diff --git a/.claude/hooks.json b/.claude/hooks.json
index 446cbc88..2bee3573 100644
--- a/.claude/hooks.json
+++ b/.claude/hooks.json
@@ -7,6 +7,10 @@
           {
             "type": "command",
             "command": ".claude/hooks/release-guard.sh"
+          },
+          {
+            "type": "command",
+            "command": ".claude/hooks/help-faq-protect.sh"
           }
         ]
       },
@@ -42,7 +46,7 @@
         "hooks": [
           {
             "type": "prompt",
-            "prompt": "Check if this file edit touches an Untether runner:\n\nFile: {{tool_input.file_path}}\n\nIf the path matches src/untether/runners/*.py or src/untether/runner.py, respond with:\nRUNNER CONTEXT:\n- Maintain the 3-event contract: StartedEvent -> ActionEvent(s) -> CompletedEvent (exactly one, always last)\n- Use EventFactory for event creation (src/untether/events.py)\n- If editing claude.py: preserve PTY lifecycle (openpty/setraw/close) and session registries (_SESSION_STDIN, _REQUEST_TO_SESSION)\n- If editing translate(): update corresponding test fixtures and reference docs in docs/reference/runners/\n- Run: uv run pytest tests/test_*_runner.py tests/test_claude_control.py -x\n\nIf the path matches src/untether/schemas/*.py, respond with:\nSCHEMA CONTEXT:\n- msgspec schema changes affect JSONL parsing (fields silently ignored if absent)\n- Check runner translate() still handles the new/changed fields\n- Update reference docs (stream-json-cheatsheet.md) and test fixtures\n\nIf the path matches src/untether/telegram/*.py, respond with:\nTELEGRAM CONTEXT:\n- All writes go through TelegramOutbox (never call Bot API directly from handlers)\n- Callback data max 64 bytes (format: prefix:action:id)\n- Call answerCallbackQuery promptly to clear spinner\n- For approval buttons: use early answering (answer_early=True, early_answer_toast())\n- Ephemeral messages: register via register_ephemeral_message() for auto-cleanup\n\nOtherwise respond: PASS"
+            "prompt": "Check if this file edit touches an Untether runner:\n\nFile: {{tool_input.file_path}}\n\nIf the path matches src/untether/runners/*.py or src/untether/runner.py, respond with:\nRUNNER CONTEXT:\n- Maintain the 3-event contract: StartedEvent -> ActionEvent(s) -> CompletedEvent (exactly one, always last)\n- Use EventFactory for event creation (src/untether/events.py)\n- If editing claude.py: preserve PTY lifecycle (openpty/setraw/close) and session registries (_SESSION_STDIN, _REQUEST_TO_SESSION)\n- If editing translate(): update corresponding test fixtures and reference docs in docs/reference/runners/\n- Run: uv run pytest tests/test_*_runner.py tests/test_claude_control.py -x\n\nIf the path matches src/untether/schemas/*.py, respond with:\nSCHEMA CONTEXT:\n- msgspec schema changes affect JSONL parsing (fields silently ignored if absent)\n- Check runner translate() still handles the new/changed fields\n- Update reference docs (stream-json-cheatsheet.md) and test fixtures\n\nIf the path matches src/untether/telegram/*.py, respond with:\nTELEGRAM CONTEXT:\n- All writes go through TelegramOutbox (never call Bot API directly from handlers)\n- Callback data max 64 bytes (format: prefix:action:id)\n- Call answerCallbackQuery promptly to clear spinner\n- For approval buttons: use early answering (answer_early=True, early_answer_toast())\n- Ephemeral messages: register via register_ephemeral_message() for auto-cleanup\n\nIf the path matches docs/faq/* or ends with docs/faq/index.md, respond with:\nHELP-FAQ CONTEXT (#477):\n- This file backs the marketing-site FAQPage Schema.org pipeline. It MUST stay in place — the FAQ-protect Bash hook prevents deletion / move / truncate-via-redirect.\n- Edits ARE encouraged: keep H2 questions and answers current as features land in CHANGELOG.md.\n- Maintain the H2-as-question shape (each `## ` heading should end with `?` or start with How / What / Why / When / Where / Can / Do / Does / Is / Are / Should / Will). The FAQPage extractor in littlebearapps/littlebearapps.com only fires on question-shaped H2s.\n- Aim for ≥7 H2 Q/A pairs (currently 12). Don't drop below 7 without coordinating with the marketing site.\n- Keep cross-links to /tutorials/, /how-to/, /help/ alive — broken links degrade the help-centre nav chain.\n- Any new question's answer should reference real Untether behaviour, not aspirational features. Source from README, real GitHub Issues, real Telegram channels.\n- See: .claude/rules/help-faq.md\n\nOtherwise respond: PASS"
           }
         ]
       },
@@ -62,7 +66,7 @@
         "hooks": [
           {
             "type": "prompt",
-            "prompt": "Check if this edit bumped a version in pyproject.toml:\n\nFile: {{tool_input.file_path}}\n\nIf the file path ends with 'pyproject.toml' AND the edit changed a line containing 'version =', respond with:\nRELEASE CHECKLIST:\n1. Create GitHub issues for all bug fixes/changes in this release (label: bug/enhancement)\n2. Add CHANGELOG.md entry: `## vX.Y.Z (YYYY-MM-DD)` with issue links [#N](...)\n3. Run `uv lock` to sync the lockfile\n4. Verify: `uv run pytest && uv run ruff check src/`\n5. Semantic versioning: patch (bug fixes), minor (new features), major (breaking changes)\n\n⚠️ MANDATORY INTEGRATION TESTING — see docs/reference/integration-testing.md\nAll tiers are fully automated via Telegram MCP tools (send_message, get_history, list_inline_buttons, press_inline_button, reply_to_message, send_voice, send_file) and Bash (journalctl, kill -TERM).\nBefore tagging this release, run the integration test suite against @untether_dev_bot (NEVER use @hetz_lba1_bot for dev testing):\n- PATCH: Tier 7 (command smoke) + Tier 1 (affected engine + Claude) + relevant Tier 6 (~30 min)\n- MINOR: Tier 7 + Tier 1 (all 6 engines) + Tier 2 (Claude interactive) + relevant Tier 3-4 + Tier 6 + upgrade path (~75 min)\n- MAJOR: ALL tiers (1-7), ALL engines, full upgrade path testing (~120 min)\n\nRestart dev bot first: systemctl --user restart untether-dev\nTail logs: journalctl --user -u untether-dev -f\nAfter tests: check logs for warnings/errors, create GitHub issues for Untether bugs, note engine quirks separately.\nDo NOT skip integration testing. Unit tests alone are insufficient.\n\n⚠️ MANDATORY STAGING (minor/major releases):\n6. Stage rc: bump to X.Y.ZrcN, push master → TestPyPI, install via scripts/staging.sh install, dogfood on @hetz_lba1_bot for 1+ week\n7. Only after staging is stable: bump to X.Y.Z final, write changelog, tag vX.Y.Z\nNEVER skip staging for minor/major releases. NEVER go directly from dev testing to PyPI tagging.\n\nOtherwise respond: PASS"
+            "prompt": "Check if this edit bumped a version in pyproject.toml:\n\nFile: {{tool_input.file_path}}\n\nIf the file path ends with 'pyproject.toml' AND the edit changed a line containing 'version =', respond with:\nRELEASE CHECKLIST:\n1. Create GitHub issues for all bug fixes/changes in this release (label: bug/enhancement)\n2. Add CHANGELOG.md entry: `## vX.Y.Z (YYYY-MM-DD)` with issue links [#N](...)\n3. Run `uv lock` to sync the lockfile\n4. Verify: `uv run pytest && uv run ruff check src/`\n5. Semantic versioning: patch (bug fixes), minor (new features), major (breaking changes)\n6. FAQ TOUCH-UP CHECK (#477): scan the new CHANGELOG entries against `docs/faq/index.md`. If any entry changes engine support, auth/billing, privacy/data flow, approval semantics, cost budgets, voice transcription, or install/update/uninstall paths — update the FAQ in the SAME release branch. Edits via Edit/Write are encouraged; deletion is gate-protected by `.claude/hooks/help-faq-protect.sh`. See `.claude/rules/help-faq.md`.\n\n⚠️ MANDATORY INTEGRATION TESTING — see docs/reference/integration-testing.md\nAll tiers are fully automated via Telegram MCP tools (send_message, get_history, list_inline_buttons, press_inline_button, reply_to_message, send_voice, send_file) and Bash (journalctl, kill -TERM).\nBefore tagging this release, run the integration test suite against @untether_dev_bot (NEVER use @hetz_lba1_bot for dev testing):\n- PATCH: Tier 7 (command smoke) + Tier 1 (affected engine + Claude) + relevant Tier 6 (~30 min)\n- MINOR: Tier 7 + Tier 1 (all 6 engines) + Tier 2 (Claude interactive) + relevant Tier 3-4 + Tier 6 + upgrade path (~75 min)\n- MAJOR: ALL tiers (1-7), ALL engines, full upgrade path testing (~120 min)\n\nRestart dev bot first: systemctl --user restart untether-dev\nTail logs: journalctl --user -u untether-dev -f\nAfter tests: check logs for warnings/errors, create GitHub issues for Untether bugs, note engine quirks separately.\nDo NOT skip integration testing. Unit tests alone are insufficient.\n\n⚠️ MANDATORY STAGING (minor/major releases):\n6. Stage rc: bump to X.Y.ZrcN, push master → TestPyPI, install via scripts/staging.sh install, dogfood on @hetz_lba1_bot for 1+ week\n7. Only after staging is stable: bump to X.Y.Z final, write changelog, tag vX.Y.Z\nNEVER skip staging for minor/major releases. NEVER go directly from dev testing to PyPI tagging.\n\nOtherwise respond: PASS"
           },
           {
             "type": "command",
diff --git a/.claude/hooks/help-faq-protect.sh b/.claude/hooks/help-faq-protect.sh
new file mode 100755
index 00000000..1f3975f8
--- /dev/null
+++ b/.claude/hooks/help-faq-protect.sh
@@ -0,0 +1,90 @@
+#!/bin/bash
+# help-faq-protect.sh — PreToolUse hook for Bash tool
+# Blocks deletion / move-out-of-place of `docs/faq/faq.md`.
+# The file is part of the marketing-site FAQPage Schema.org pipeline
+# (issue #477; renamed from index.md → faq.md in #483 to expose
+# `/help/untether/faq/` instead of `/help/untether/index/`).
+# Removing it breaks the docs-sync mapping registered in
+# `littlebearapps/littlebearapps.com:scripts/docs-sync.config.ts` and
+# would silently regress AI-citation surface (ChatGPT, Perplexity,
+# Google AI Overviews) on the next deploy.
+#
+# This hook deliberately does NOT block edits — the FAQ is meant to be
+# updated as features land. It only blocks destructive ops (rm, git rm,
+# mv away, redirected truncation).
+
+set -euo pipefail
+
+INPUT=$(cat)
+COMMAND=$(echo "$INPUT" | jq -r '.tool_input.command // ""' 2>/dev/null)
+[ -z "$COMMAND" ] && echo '{}' && exit 0
+
+# Helper: emit Claude Code PreToolUse deny shape (2026+).
+deny() {
+  jq -n --arg r "$1" '{
+    hookSpecificOutput: {
+      hookEventName: "PreToolUse",
+      permissionDecision: "deny",
+      permissionDecisionReason: $r
+    }
+  }'
+  exit 0
+}
+
+match_target='(^|[^A-Za-z0-9_/])docs/faq/(faq\.md|\*|.\*|\.\.|.*\.md)?'
+
+# 1. `rm` / `unlink` / `shred`
+if echo "$COMMAND" | grep -qE '(^|[^A-Za-z_])(rm|unlink|shred)([[:space:]]|$)'; then
+  if echo "$COMMAND" | grep -qE "$match_target"; then
+    deny "🛑 HELP-FAQ PROTECTION: docs/faq/faq.md cannot be deleted.
+
+This file backs the marketing-site FAQPage Schema.org pipeline
+(see issue #477). Removing it silently regresses AI-citation
+surface on the next docs-sync deploy.
+
+You CAN edit it freely — the FAQ should be updated as features
+land. To replace content, edit in-place; do not delete and recreate.
+
+To genuinely retire the FAQ, raise an issue first to coordinate
+the matching mapping removal in
+\`littlebearapps/littlebearapps.com:scripts/docs-sync.config.ts\`."
+  fi
+fi
+
+# 2. `git rm`
+if echo "$COMMAND" | grep -qE '\bgit\b[[:space:]]+rm\b'; then
+  if echo "$COMMAND" | grep -qE "$match_target"; then
+    deny "🛑 HELP-FAQ PROTECTION: docs/faq/faq.md cannot be \`git rm\`'d.
+
+The file backs the marketing-site FAQPage Schema.org pipeline (#477).
+Edit in place instead. If retirement is genuinely needed, coordinate
+with littlebearapps/littlebearapps.com first."
+  fi
+fi
+
+# 3. `mv` away from docs/faq/.
+if echo "$COMMAND" | grep -qE '(^|[^A-Za-z_])mv([[:space:]]|$)'; then
+  if echo "$COMMAND" | grep -qE 'docs/faq/faq\.md[[:space:]]+[^[:space:]]+'; then
+    deny "🛑 HELP-FAQ PROTECTION: docs/faq/faq.md cannot be moved.
+
+The path is referenced by the marketing-site docs-sync config
+(\`scripts/docs-sync.config.ts\` in littlebearapps/littlebearapps.com).
+Renaming/moving silently breaks the FAQPage schema pipeline (#477).
+
+Edit in place. To genuinely relocate, coordinate with the marketing
+site first."
+  fi
+fi
+
+# 4. Redirect truncation (`>` not `>>`).
+if echo "$COMMAND" | grep -qE '(^|[^>])>[[:space:]]*docs/faq/faq\.md\b'; then
+  deny "🛑 HELP-FAQ PROTECTION: shell redirect (\`>\`) would truncate docs/faq/faq.md.
+
+Use the Edit tool for in-place changes, or \`>>\` to append, so the
+file's identity (and the FAQPage schema pipeline #477) is preserved.
+
+If you need to fully replace the file content, use the Write tool —
+that's an in-place rewrite, not a deletion."
+fi
+
+echo '{}'
diff --git a/.claude/hooks/release-guard-protect.sh b/.claude/hooks/release-guard-protect.sh
index 6cc1e682..f3487155 100755
--- a/.claude/hooks/release-guard-protect.sh
+++ b/.claude/hooks/release-guard-protect.sh
@@ -27,6 +27,9 @@ case "$FILE_PATH" in
   */release-guard.sh | */release-guard-protect.sh | */release-guard-mcp.sh)
     deny "🛑 RELEASE GUARD: This file is protected.\n\nRelease guard hooks can only be edited manually by Nathan.\nProtected: .claude/hooks/release-guard*.sh"
     ;;
+  */help-faq-protect.sh)
+    deny "🛑 HELP-FAQ PROTECTION: This hook script is protected.\n\nThe FAQ-protect hook can only be edited manually by Nathan to prevent silent removal of docs/faq/index.md (issue #477).\nProtected: .claude/hooks/help-faq-protect.sh"
+    ;;
   */.claude/hooks.json)
     deny "🛑 RELEASE GUARD: .claude/hooks.json is protected.\n\nHook configuration must be edited manually by Nathan to prevent removal of release guard hooks."
     ;;
diff --git a/.claude/rules/help-faq.md b/.claude/rules/help-faq.md
new file mode 100644
index 00000000..1de2701a
--- /dev/null
+++ b/.claude/rules/help-faq.md
@@ -0,0 +1,117 @@
+# Help-Centre FAQ Rules (`docs/faq/faq.md`)
+
+`docs/faq/faq.md` is the user-facing FAQ for Untether. It backs the
+marketing-site **FAQPage Schema.org** pipeline shipped in
+[`littlebearapps/littlebearapps.com`](https://github.com/littlebearapps/littlebearapps.com)
+on `feature/help-seo-geo-items-1-4`. Once the docs-sync mapping (`scripts/docs-sync.config.ts`)
+under the `untether` entry references `docs/faq` with `category: faq`,
+the marketing site emits `<script type="application/ld+json">` `FAQPage`
+JSON-LD on every deploy — unlocking AI-citation surface (ChatGPT,
+Perplexity, Google AI Overviews) and SERP rich-snippet eligibility for
+the Untether help articles.
+
+Tracking issue: [#477](https://github.com/littlebearapps/untether/issues/477).
+
+## Hard rules
+
+### NEVER delete or move the file
+
+- The path is referenced by the upstream marketing-site sync config.
+  Removing it silently breaks the docs-sync mapping (`build-error` per
+  the issue's "Coordinated mapping" note) and regresses the FAQPage
+  schema on the next deploy.
+- The repo enforces this via `.claude/hooks/help-faq-protect.sh`
+  (PreToolUse Bash hook). It blocks `rm`, `git rm`, `mv`-away, and
+  shell-redirect (`>`) truncation. Append (`>>`) and Edit/Write are
+  intentionally NOT blocked — the FAQ is meant to evolve.
+- To genuinely retire the FAQ, raise an issue first to coordinate the
+  matching mapping removal in `littlebearapps/littlebearapps.com`.
+
+### MUST stay current with feature changes
+
+- Treat the FAQ like a contract with users. Whenever a new feature
+  lands in `CHANGELOG.md`, ask: does the existing FAQ still answer
+  questions correctly?
+- Specifically watch for:
+  - **Engine support changes** — Q3 ("Which AI coding agents…")
+    enumerates the 6 supported engines. If a new engine lands or one is
+    deprecated, update.
+  - **Subscription / API key model changes** — Q4 ("Do I need an API
+    key?") describes which engines use OAuth vs API key. Any auth-flow
+    changes need an FAQ refresh.
+  - **Privacy / data flow changes** — Q5 ("Where does my code and data
+    go?") covers Telegram, agent CLI, vendor, and Untether itself.
+    Any new outbound network call or telemetry MUST be reflected here.
+  - **Approval-flow changes** — Q6 ("How do I approve tool calls…")
+    documents Plan mode buttons and `/planmode` semantics. Any change
+    to ExitPlanMode, ask-mode, or per-engine approval policies needs
+    an FAQ pass.
+  - **Cost / budget changes** — Q8 ("How do I keep agents from
+    spending too much…") shows `[cost_budget]` config. New keys, new
+    budget types, or new auto-cancel behaviour need an FAQ refresh.
+  - **Voice transcription changes** — Q9 ("Can I send voice notes…")
+    references `voice_transcription_*` config keys. Renames or new
+    keys need an FAQ pass.
+  - **Install / update / uninstall path changes** — Q2/Q10/Q11 cover
+    `uv tool` and `pipx` flows. Any change to the wizard, default
+    config path, or systemd integration needs an FAQ refresh.
+
+## Soft conventions
+
+### Question shape
+
+- Each `## ` heading MUST be a question. The FAQPage extractor in the
+  marketing site only fires on question-shaped H2s — bare topic
+  headings like `## Installation` are silently ignored by the schema.
+- Phrase as: ends with `?`, OR starts with How / What / Why / When /
+  Where / Can / Do / Does / Is / Are / Should / Will.
+- Aim for ≥7 H2 Q/A pairs (the issue's acceptance criterion). Currently
+  ships with 12. Don't drop below 7 without coordinating with the
+  marketing site.
+
+### Answer style
+
+- Each answer is a complete paragraph (or short bullet list with a
+  closing sentence). No `TODO`, no `[placeholder]`, no `TBD`.
+- Cross-link to existing help-guide URLs (`/tutorials/`, `/how-to/`,
+  `/help/`). Broken links degrade the help-centre nav chain — verify
+  links resolve before merging.
+- Answers should describe **real Untether behaviour**, not aspirational
+  features. Source from README, real GitHub Issues, Telegram
+  community channels.
+
+### Frontmatter
+
+- Keep frontmatter minimal: `title` + `description` only. The
+  marketing-site sync injects `category: faq`, `tool: untether`, and
+  dates automatically.
+- Don't manually set `category` or `tool` here — that's the sync
+  pipeline's job.
+
+## When to update during a release
+
+Suggested cadence as part of the [release-discipline](./release-discipline.md)
+workflow:
+
+1. After drafting the CHANGELOG entry for a new release, scan the
+   entries against the "MUST stay current" list above.
+2. If any FAQ-relevant entry exists, edit `docs/faq/faq.md`
+   in-place. Rephrase, add a new Q/A, or update the cross-link.
+3. Commit the FAQ touch-up alongside the release commits in the same
+   feature branch (don't fragment into a separate PR unless the FAQ
+   change is substantial).
+4. The marketing-site sync runs nightly and on demand — no manual
+   trigger needed once the file is updated.
+
+## After changes
+
+```bash
+# 1. Verify shape: ≥7 H2 question-shaped headings, no placeholders
+grep -c '^## ' docs/faq/faq.md   # should be ≥ 7
+grep -ciE 'TODO|\[placeholder\]|TBD|XXX' docs/faq/faq.md   # should be 0
+
+# 2. Verify each H2 starts with a question word OR ends with ?
+grep '^## ' docs/faq/faq.md | \
+  grep -vE '^##.*\?$|^## (How|What|Why|When|Where|Can|Do|Does|Is|Are|Should|Will)\b'
+# (no output = all H2s are question-shaped)
+```
diff --git a/.claude/rules/release-discipline.md b/.claude/rules/release-discipline.md
index fd7e6d6b..bef85c29 100644
--- a/.claude/rules/release-discipline.md
+++ b/.claude/rules/release-discipline.md
@@ -13,6 +13,7 @@
 3. Every changelog entry must link to a GitHub issue: `[#N](https://github.com/littlebearapps/untether/issues/N)`
 4. Run `uv lock` to sync the lockfile
 5. **Run integration tests against `@untether_dev_bot`** — see below and `docs/reference/integration-testing.md`
+6. **FAQ touch-up check (`docs/faq/faq.md`)** — scan the new CHANGELOG entries against the help-centre FAQ. If any entry changes engine support, auth/billing model, privacy/data flow, approval semantics, cost budgets, voice transcription config, install/update/uninstall paths, or any other user-facing surface answered by the FAQ, update `docs/faq/faq.md` in the same release branch. The file is gate-protected — Bash `rm`/`mv`/`>` are blocked by `help-faq-protect.sh`, but Edit/Write are encouraged. See [`help-faq.md`](./help-faq.md) for the full update cadence and shape rules. Tracking issue: [#477](https://github.com/littlebearapps/untether/issues/477).
 
 ## Semantic versioning
 
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 1380be73..d5c2d09d 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -50,7 +50,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
           enable-cache: true
@@ -84,7 +84,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: ${{ matrix.python-version }}
           enable-cache: true
@@ -114,7 +114,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.13"
           enable-cache: true
@@ -128,7 +128,7 @@ jobs:
           uvx check-wheel-contents dist/*.whl
 
       - name: Upload packages
-        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
         with:
           name: Packages
           path: dist/
@@ -148,7 +148,7 @@ jobs:
           path: dist/
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
 
@@ -207,7 +207,7 @@ jobs:
         include:
           - task: pip-audit
             do_sync: true
-            command: uv run --no-sync pip-audit --skip-editable --progress-spinner=off --ignore-vuln CVE-2026-4539  # pygments 2.19.2, no fix available
+            command: uv run --no-sync pip-audit --skip-editable --progress-spinner=off --ignore-vuln CVE-2026-4539 --ignore-vuln CVE-2026-3219 --ignore-vuln CVE-2026-6357  # CVE-2026-4539 pygments (fixed in 2.20.0 lockfile bump #402); CVE-2026-3219 + CVE-2026-6357 pip itself, fix in pip 26.1 not yet pulled by uv tooling
             sync_args: ""
           - task: bandit
             do_sync: true
@@ -218,7 +218,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
           enable-cache: true
diff --git a/.github/workflows/codeql.yml b/.github/workflows/codeql.yml
index 5115dc45..1b4ff1a1 100644
--- a/.github/workflows/codeql.yml
+++ b/.github/workflows/codeql.yml
@@ -31,11 +31,11 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Initialise CodeQL
-        uses: github/codeql-action/init@820e3160e279568db735cee8ed8f8e77a6da7818 # v3.32.6
+        uses: github/codeql-action/init@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           languages: ${{ matrix.language }}
 
       - name: Run analysis
-        uses: github/codeql-action/analyze@820e3160e279568db735cee8ed8f8e77a6da7818 # v3.32.6
+        uses: github/codeql-action/analyze@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           category: "/language:${{ matrix.language }}"
diff --git a/.github/workflows/dependabot-auto-merge.yml b/.github/workflows/dependabot-auto-merge.yml
index f8f91a3b..e35b8ca5 100644
--- a/.github/workflows/dependabot-auto-merge.yml
+++ b/.github/workflows/dependabot-auto-merge.yml
@@ -14,7 +14,7 @@ jobs:
     steps:
       - name: Fetch Dependabot metadata
         id: metadata
-        uses: dependabot/fetch-metadata@21025c705c08248db411dc16f3619e6b5f9ea21a # v2.5.0
+        uses: dependabot/fetch-metadata@25dd0e34f4fe68f24cc83900b1fe3fe149efef98 # v3.1.0
         with:
           github-token: "${{ secrets.GITHUB_TOKEN }}"
 
diff --git a/.github/workflows/prerelease-deps.yml b/.github/workflows/prerelease-deps.yml
index 91c5458d..bf10509e 100644
--- a/.github/workflows/prerelease-deps.yml
+++ b/.github/workflows/prerelease-deps.yml
@@ -19,7 +19,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
           enable-cache: true
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index e1d9ff1a..e751d4aa 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -19,7 +19,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
           enable-cache: true
@@ -67,7 +67,7 @@ jobs:
           uvx check-wheel-contents dist/*.whl
 
       - name: Upload packages
-        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
         with:
           name: Packages
           path: dist/
@@ -107,7 +107,7 @@ jobs:
         uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Install uv
-        uses: astral-sh/setup-uv@6ee6290f1cbc4156c0bdd66691b2c144ef8df19a # v7.4.0
+        uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b # v8.1.0
         with:
           python-version: "3.14"
           enable-cache: true
diff --git a/CHANGELOG.md b/CHANGELOG.md
index ab194d84..e7b314b3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,56 @@
 # changelog
 
+## v0.35.3 (unreleased)
+
+### breaking
+
+- **security:** empty `[transports.telegram] allowed_user_ids` is now a startup `ConfigError` instead of a silent insecure default. Previously, an unset or empty allowlist meant any Telegram user who knew the bot username could send commands — a real production-bot footgun. Operators who want an open bot (demos, hackathons, dev) must opt in explicitly with `allow_any_user = true`, which is logged at INFO every boot (`security.allow_any_user`) so the deviation stays visible in `journalctl`. Existing deployments already configured with a populated allowlist are unaffected; deployments running with an empty allowlist will fail to start until the operator either populates the list or sets the opt-out flag. Migration is a one-line config edit. The legacy-config migration in `config_migrations.py` now relocates a top-level `allow_any_user` key into `[transports.telegram]` alongside `bot_token` / `chat_id`. New `_validate_allowed_user_ids_or_optin` `@model_validator` in `TelegramTransportSettings`. 4 new tests in `tests/test_settings.py` (block + opt-out + populated + both-set) [#377](https://github.com/littlebearapps/untether/issues/377)
+
+### changes
+
+- **feat:** Gemini runner now passes `--skip-trust` by default so headless runs work outside `~/.gemini/trustedFolders.json`. Gemini CLI rejects runs from any directory not in the trust list — even with `--approval-mode yolo` — and there is no interactive prompt path in headless usage, so projects outside the trust list silently failed before any agent output. Untether already runs Gemini with `yolo` for the same "always headless" reason, so passing `--skip-trust` extends the same precedent. `GeminiRunner.skip_trust` (default `True`) is the runtime switch; opt out per deployment with `[gemini] skip_trust = false` in `untether.toml` (security-conscious operators who want Gemini's project-local extension/MCP trust gate enforced). 2 new tests in `tests/test_build_args.py::TestGeminiBuildArgs` (`test_skip_trust_default_includes_flag`, `test_skip_trust_opt_out_omits_flag`) [#471](https://github.com/littlebearapps/untether/issues/471)
+- **feat:** hot-reload `[progress]` settings — editing `[progress].max_actions`, `[progress].verbosity`, `[progress].min_render_interval`, or `[progress].group_chat_rps` in `untether.toml` now applies on the next run without restarting the bot. Companion to the trigger hot-reload (#294) and bridge hot-reload (#286/#318) shipped earlier this milestone. The four settings groups in scope for #269 each had a different starting state: `[footer]` and `[cost]` were already reading fresh per-call from `_load_footer_settings()` / `load_settings_if_exists()` (no work needed); `[watchdog]` was already reading fresh per-run via `_load_watchdog_settings()` at the top of `handle_message` (still no restart-required, just verified); the only gap was `[progress]`, where `MarkdownFormatter(max_actions, verbosity)` and `ExecBridgeConfig.min_render_interval` were baked in at startup in `telegram/backend.py`. Closed by adding `MarkdownFormatter.refresh_from(progress_settings)` and `TelegramPresenter.refresh_progress_settings()`, plus a new `runner_bridge._load_progress_settings()` sibling helper that `handle_message` invokes per-run; the runner bridge now refreshes the default presenter's formatter (per-chat `/verbose` overrides downstream of `_resolve_presenter` reconstruct from the refreshed defaults so they pick up the new values too) and threads the live `min_render_interval` into each `ProgressEdits` instance instead of the startup snapshot. Out of scope (entry-point limitation, documented on the issue): engine registration and command registration — those still require `pipx upgrade` / restart. 8 new tests in `tests/test_meta_line.py` (`TestMarkdownFormatterRefresh`: max_actions, verbosity, negative-clamp, invalid-verbosity rejection, missing-attribute tolerance, presenter delegation; plus `_load_progress_settings` defaults / error-fallback covers). Full suite: 2511 passed [#269](https://github.com/littlebearapps/untether/issues/269)
+- **feat:** Claude post-result idle timeout + "✓ turn complete" UX hint (Option D hybrid). Closes the "session looks stuck for 36 min after final message" gap by combining (a) an immediate footer signal so the user knows the turn is done, and (b) a server-side timer that closes stdin when the bidirectional Claude CLI sits idle past the new `[watchdog].post_result_idle_timeout` (default 600s, range 30s–1h; gated by `[watchdog].post_result_idle_enabled = true` for an explicit kill-switch). Mechanism: `ClaudeStreamState.result_received_at` is armed by `translate_claude_event` on every `StreamResultMessage`; a new `ClaudeRunner._post_result_idle_watchdog` task started in the `run_impl` task group polls the timer and calls `this_proc_stdin.aclose()` once the deadline passes — same mechanism as the normal-flow exit on line 2412, just earlier. The CLI hits stdin EOF and exits gracefully (rc=0); the auto-continue safety gate already excludes `last_event_type == "result"` (locked by `test_skips_result_event_type` from #34142's regression set) so the clean exit will not phantom-resume the session. Approval-state guard: if `_REQUEST_TO_SESSION` or `_PENDING_ASK_REQUESTS` has live entries for this session the timer re-arms instead of closing — prevents orphaning a button-click control_response that's mid-flight. UX hint #1 is delivered via a supplementary `StartedEvent` carrying `meta={"complete": "✓ turn complete"}` (the supported pattern for late-arriving meta per `runner-development.md`); `markdown.format_meta_line` renders it in the footer alongside model/effort/permission/trigger so the user immediately sees the turn boundary. Successful results emit the hint; errored results don't (no false "complete" tag on a failure). Two structlog events for ops: `claude.post_result_idle.deferred` (when the approval guard fires) and `claude.post_result_idle.closing_stdin` (when the deadline passes cleanly). 6 new tests in `tests/test_claude_runner.py` (`test_translate_result_arms_post_result_idle_timer`, `test_translate_result_emits_turn_complete_meta`, `test_translate_result_skips_complete_meta_on_error`, `test_post_result_idle_watchdog_fires_when_clean`, `test_post_result_idle_watchdog_defers_when_pending_approval`, `test_meta_line_renders_turn_complete_marker`, `test_meta_line_omits_complete_when_absent`) [#333](https://github.com/littlebearapps/untether/issues/333)
+- **feat:** trigger visibility Tier 2 (`/config:tg` page expansion) + Tier 3 (`last_fired_at` history + `/stats` triggered/manual breakdown). The `/config → ⏰ Triggers` page now lists every cron and webhook configured for the current chat — for crons, the human-readable schedule via `describe_cron(schedule, timezone)`, project, engine, and last-fired relative time; for webhooks, path, auth scheme, project, engine, and last-fired. Lists are scoped to the current chat (using `crons_for_chat` / `webhooks_for_chat` with the bridge `default_chat_id` fallback), capped at 10 entries with a "…and N more (see untether.toml)" overflow marker, and omitted entirely when the chat has no triggers (the pause/resume controls remain at the top regardless). Tier 3 adds a new persistent JSON history store (`src/untether/triggers/history.py`) at `<config_path>.with_name("triggers_history.json")` that records `time.time()` after every successful cron dispatch (`triggers/cron.py:130` post-`dispatch_cron`) and webhook fire (`triggers/dispatcher.py:dispatch_webhook` and `dispatch_action` for non-agent actions). Recording is best-effort — `OSError` writes log `triggers.history.write_failed` and swallow so a transient disk failure can't break the cron loop or webhook server. `/stats` now appends `(N triggered, M manual)` per engine line and on the totals row when at least one count is > 0; `DayBucket` and `AggregatedStats` carry additive `triggered_count` / `manual_count` fields with `.get(..., 0)` fallbacks so existing `stats.json` files load cleanly. `runner_bridge.handle_message` resolves the split via `triggered=bool(context and context.trigger_source)` at the existing `record_run` callsite. New `triggers_history.json` state file is created on demand and survives restart; renaming a trigger ID in TOML leaves a stale entry that operators can manually delete (no auto-prune to avoid losing data on transient TOML errors). 28 new tests across `tests/test_triggers_history.py` (10), `tests/test_session_stats.py::triggered/manual` (7), `tests/test_stats_command.py` (3), `tests/test_config_command.py::TestTriggersPagePerChat` (7), `tests/test_trigger_cron.py` (2 cron-firing + history-failure resilience), and `tests/test_trigger_dispatcher.py` (2 webhook recording + history-failure resilience) [#271](https://github.com/littlebearapps/untether/issues/271)
+- **feat:** subscription-usage observability + `/usage debug` section. Promotes the `claude_usage.schema_mismatch` structlog warning from one-shot per-process to per-call counter so the issue-watcher fires on ongoing API-shape drift, not just the first hit (the structured event now carries a cumulative `count` field; new `runner_bridge.get_usage_schema_mismatch_count()` exposes the same counter for the debug page). Adds `UsageCacheStats` to `utils/usage_cache.py` tracking last successful fetch wall time, cache age, last-error class+message; populated by `fetch_claude_usage_cached` on every fetch path including stale-while-error fallbacks. Adds `_read_token_expiry_ms()` to `telegram/commands/usage.py` so the OAuth token expiry can be surfaced without raising on missing credentials. New `/usage debug` invocation appends a `🔧 debug` block (HTML-formatted) showing: last successful fetch (UTC ISO timestamp + age + freshness label), last error (class + message, truncated), OAuth token expiry (with hh/mm-until-expiry), and the cumulative schema-mismatch counter — operator-facing signal so the next time the subscription footer goes silent the root cause is visible without grepping `journalctl`. 5 new tests in `tests/test_usage_cache.py::TestCacheStatsObservability` (initial state, success records wall time, failure records last error, success-then-failure preserves wall time) and `tests/test_command_engine_gates.py::TestUsageDebugMode` (debug section appended only when `args_text == "debug"`); existing `test_schema_mismatch_warning_fires_once` repurposed to assert per-call firing with cumulative counts [#410](https://github.com/littlebearapps/untether/issues/410)
+- **feat:** `CLAUDE_STREAM_IDLE_TIMEOUT_MS` is now user-configurable via `[watchdog] claude_stream_idle_timeout_ms` in `untether.toml` (default 300000 ms / 5 min, range 30 s – 30 min). Deployments that hit upstream Anthropic API stalls on long opus 4.7 1M plan-mode generations (Type-A mid-generation stalls) can raise this to 600000–900000 ms to ride out longer SSE silences. Untether's Claude runner reads the value via `setdefault` so shell-set `CLAUDE_STREAM_IDLE_TIMEOUT_MS` still wins. Settings load failure falls back to the hardcoded 300000 ms default with a debug log entry. **Type-A vs Type-B classification on the failure message**: when the run fails with `API Error: Stream idle timeout - partial response received`, the `_extract_error` output now appends a one-line classification: Type-A (mid-generation, `num_turns ≥ 1 && duration_api_ms > 0`) suggests raising the timeout; Type-B (cold-start zero-byte stall, `num_turns ≤ 1 && duration_api_ms == 0`) explicitly tells the user that raising the timeout will NOT help — it's an upstream API outage, not a local watchdog miscalibration. Auto-retry deferred to v0.35.4 pending upstream Anthropic stabilisation. 5 new tests in `test_claude_runner.py` (`test_extract_error_type_a_*`, `test_extract_error_type_b_*`, `test_extract_error_unrelated_*`, `test_env_stream_idle_timeout_configured_value`, `test_env_stream_idle_timeout_settings_load_failure_falls_back`) [#438](https://github.com/littlebearapps/untether/issues/438)
+- **feat:** master pause/resume toggle for the trigger system (crons + webhooks). Adds `TriggerManager.pause()` / `resume()` / `is_paused` API; cron scheduler skips its tick while paused (`run_once` crons are not consumed during the pause and fire on the next matching tick after resume); webhook server returns `503 triggers paused` (with `Retry-After: 60`) instead of dispatching, and the `/health` endpoint surfaces `{"status":"paused","paused":true}` so external monitors can distinguish paused-but-up from healthy. Pause is in-memory only — restart auto-resumes (the safe default). Wired into `/config` two ways: a one-button toggle row at the bottom of the home page (only when triggers are configured) and a dedicated `📡 Triggers` page (`config:tg`) with state + counts. `/ping` switches to a `⏸ triggers paused: … (suspended)` indicator while paused. 8 new tests in `test_trigger_manager.py` (`TestPauseToggle`), 2 in `test_ping_command.py` (paused/resumed indicators), 5 in `test_config_command.py` (`TestTriggersPage`) covering unavailable / empty / pause / resume / toast labels [#294](https://github.com/littlebearapps/untether/issues/294)
+- **feat:** `[claude]` config gains `extra_args: list[str]` — user-supplied upstream CLI flags passed through to `claude` verbatim. Mirrors `codex.extra_args` and `pi.extra_args`. Primary motivator is Claude-in-Chrome: Claude Code 2.1.x gates the `mcp__claude-in-chrome__*` tool namespace behind `--chrome` (or `CLAUDE_CODE_ENABLE_CFC=1`), so Untether-spawned sessions never saw those tools in their catalogue. Setting `extra_args = ["--chrome"]` in `~/.untether/untether.toml` now enables Claude-in-Chrome end-to-end without forking Untether or touching the LaunchAgent/systemd env. Flags Untether manages internally (`-p`, `--print`, `--output-format`, `--input-format`, `--resume`/`-r`, `--continue`/`-c`, `--permission-mode`, `--permission-prompt-tool`) are rejected at config-load with a `ConfigError` so duplicate-argv surprises fail fast instead of at runtime. The user-supplied args land on argv after Untether's managed stream-json prelude and before resume / model / effort / allowed-tools / permission flags, so the trailing `-p <prompt>` (or stdin prompt under permission-mode) is never displaced. 8 new unit tests in `tests/test_build_args.py` cover argv ordering, permission-mode argv, multi-flag order preservation, `build_runner` parsing, and reserved-flag rejection (individual flag + `key=value` prefix form) [#407](https://github.com/littlebearapps/untether/issues/407)
+- **feat:** user-extensible engine-subprocess env allowlist — two new `[security]` keys let self-installed Untether users thread credential-manager tokens (1Password, Doppler, Vault, Infisical, …) into engine subprocesses without forking `utils/env_policy.py`. `env_extra_allow: list[str]` admits exact names (e.g. `OP_SERVICE_ACCOUNT_TOKEN`); `env_extra_prefix_allow: list[str]` admits whole families (e.g. `VAULT_*` via `["VAULT_"]`). Both are validated against `[A-Z_][A-Z0-9_]*` at config-load — empty / whitespace / lowercase / leading-digit entries are rejected. Honoured by the Claude and Pi runners (the engines that opt in to `filtered_env`) and by the `env_audit` probe (so user-allowed names aren't false-flagged as `claude.env_audit.leaked_var`). One `env_policy.user_extension` INFO log per process at first runner spawn. `BWS_ACCESS_TOKEN` (Bitwarden Secrets Manager — common enough to ship by default) is also promoted into the built-in `_EXACT_ALLOW`. 19 new tests across `test_env_policy.py`, `test_env_audit.py`, `test_settings.py` [#409](https://github.com/littlebearapps/untether/issues/409)
+- **feat:** `/trigger` command renamed to `/listen` to disambiguate from the webhook/cron triggers system. The chat-level message-routing command (`all` / `mentions` / `clear`) shared its name with the unrelated `[triggers]` TOML section, which became increasingly confusing as `/config` grew separate trigger pages. `/listen` is now the canonical command; `/trigger` continues to work as a deprecated alias for one release cycle and prepends a one-line deprecation notice on each invocation. `/config → 📡 Listen` page replaces the prior `📡 Trigger` page; the home-page summary renders `Listen: all` instead of `Trigger: all`; bot command menu lists `listen`. Internal renames: `telegram/trigger_mode.py` → `telegram/listen_mode.py`; `commands/trigger.py` → `commands/listen.py`; type `TriggerMode` → `ListenMode`; `resolve_trigger_mode()` → `resolve_listen_mode()`; ChatPrefsStore / TopicStateStore gain new `*_listen_mode` methods with legacy `*_trigger_mode` aliases preserved for one cycle. Storage: msgspec field is still named `trigger_mode` for backward compat with existing `telegram_chat_prefs_state.json` / `telegram_topics_state.json` — no migration needed [#297](https://github.com/littlebearapps/untether/issues/297)
+- **feat:** long-running tool visibility — Bash, BashOutput, ScheduleWakeup, Monitor, and any other tool > 60 s now surfaces a heartbeat-driven elapsed-time tail on the progress message (`▸ Bash · 3m 47s · npm run build`) so a glancing user can answer "is it alive? what is it doing? for how long?" without waiting for the next JSONL event. Two coordinated upgrades: (1) a 30 s heartbeat tick (new `[progress] heartbeat_interval`, range 5–120 s, default 30) folded into the existing stall monitor — every tick walks `ProgressTracker._actions` and bumps `event_seq` whenever any open action's `started_at` is older than 60 s, forcing a re-render with a fresh elapsed counter; (2) `format_action_line` gained an `elapsed_seconds` kwarg that appends ` · <elapsed> · <key arg>` for non-completed actions, regardless of the `/verbose` toggle. `format_verbose_detail` gained dedicated branches for `BashOutput` (renders the last line of `result_preview` so 10-min Cloudflare deploy polls show `→ Deploy Production: in_progress` instead of a static `▸ BashOutput`), `KillShell`, `ScheduleWakeup` (countdown + reason: `→ fires in 4m 12s · "build check"`), and `Monitor` (countdown remaining). `ActionState` gained `started_at` / `last_update_at` wall-clock fields populated from the `ProgressTracker.clock` callable (defaults to `time.monotonic`; tests can pass a fake clock for deterministic assertions). The render pipeline (`MarkdownFormatter.render_progress_parts`, `MarkdownPresenter.render_progress`, `Presenter.render_progress` Protocol, `TelegramPresenter.render_progress`) all gained an optional `now: float | None` kwarg threaded from `runner_bridge._run_loop`. New `format_duration` / `format_countdown` helpers in `markdown.py`. Strict "rolling stdout sub-line ≤ every 5 s" cannot be achieved without upstream Claude Code changes — the BashOutput-polling path is the proxy and refreshes at each polling cycle (~15 s in practice). 22 new tests across `tests/test_verbose_progress.py` (BashOutput / KillShell / ScheduleWakeup / Monitor detail + long-running tail variants + format_duration helpers) and `tests/test_exec_bridge.py` (heartbeat-driven countdown mutation) [#481](https://github.com/littlebearapps/untether/issues/481)
+- **feat:** expected-wait stall suppression matrix — five new info-logged branches in `ProgressEdits._stall_monitor` suppress Telegram stall warnings during legitimate waits, gated by a `if not frozen_escalate` master gate so genuinely-frozen sessions still warn. Branches: (1) `progress_edits.stall_post_result_suppressed` — `stream.last_event_type == "result"` and `engine_state.result_received_at` armed (the post-result idle watchdog from #333 is the legitimate owner of the silence); (2) `progress_edits.stall_schedule_wakeup_suppressed` — `engine_state.live_wakeups` has any deadline in the future (Claude is parked waiting for an upstream timer); (3) `progress_edits.stall_monitor_active_suppressed` — `engine_state.live_monitors` has any future deadline; (4) `progress_edits.stall_bash_grace_suppressed` — most-recent action is Bash/BashOutput/KillShell within the new `[watchdog] bash_grace_seconds` (range 5–300 s, default 60) startup window; (5) `progress_edits.stall_long_bash_suppressed` — recent BashOutput within `stall_threshold/2` (the polling cycle is the proxy for "stdout is flowing"). The same 5 booleans gate the `_STALL_MAX_WARNINGS` auto-cancel arm with a new `progress_edits.stall_auto_cancel_suppressed_expected_wait` log — a session about to gracefully close (#470) or legitimately waiting on a timer must not be killed. structlog WARN events at `runner.py:1002` (`subprocess.liveness_stall`) and `runner_bridge.py` (`progress_edits.stall_detected`) remain unchanged so `untether-issue-watcher` and ops dashboards continue to receive them — only the chat-side surfacing decision changed. Bash/BashOutput suppression uses `tracker._actions` engine-agnostically (mirrors `_has_running_mcp_tool`); ScheduleWakeup / Monitor / post-result use `getattr(stream, "engine_state", None)` duck-typing (Claude only today, no-ops cleanly for other engines). 11 new tests in `tests/test_exec_bridge.py` covering each suppression branch, the auto-cancel block, the closing-message idempotency, the heartbeat countdown mutation, and the frozen-ring precedence (post-result + ScheduleWakeup) [#481](https://github.com/littlebearapps/untether/issues/481)
+- **feat:** /loop and ScheduleWakeup support — opt-in observation of Claude Code's session-scoped scheduling tools so iterations keep firing after the subprocess exits. **Default OFF** — users opt in per chat via `/config → 🔁 Loop mode`. New `loop_scheduler` module sibling of `at_scheduler` (mirrors install/uninstall/active_count API) with persistence to `active_loops.json` for restart resilience. Observer hooks in the Claude runner's JSONL stream-translation path (`_observe_loop_tool_use` / `_observe_loop_tool_result`, sibling functions to the existing `_register_background_handle` / `_clear_background_handle` background-task tracker) parse the canonical Probe-5-confirmed field names (`cron` not `cron_expression`; `id` not `taskId`/`cronId`) and bind upstream 8-character cron IDs via `\bjob ([0-9a-f]{8})\b`. Race avoidance gates fire on `is_session_alive` (added pre-#289 as `3362ae9`) — if the subprocess is still parked on a control_request, the fire path sleeps `redundancy_check_interval` and retries instead of double-firing. Drop-on-busy via `is_chat_busy` callable mirrors upstream's "no catch-up" semantic. Re-issue prompts wrap the original user prompt with `Loop iteration N: <prompt>. Do the task now; do not summarize old results unless necessary.` (per Probe 3 result + consensus revision). Cost protection delegated entirely to existing `[cost_budget]` infrastructure — every loop fire calls `cost_tracker.record_run_cost`, every loop iteration is subject to the same daily/per-run caps as manual runs. New `[loop]` config section provides runaway-safety caps (`max_iterations`, `max_total_duration_hours`, `expiry_days`) but explicitly NOT cost caps. Drain integration in `_drain_and_exit` polls `loop_scheduler.active_count()` alongside `pending_at`. `/cancel` and `/new` both call `cancel_pending_for_chat` which writes the do-not-resume sentinel for the cancelled session (block only loop_scheduler `--resume`, not `/continue` per handover default). New `_page_loop()` sub-page in `/config` with explicit cost+quota warning before turning ON; engine-aware (Claude only — `LOOP_SUPPORTED_ENGINES = frozenset({"claude"})`); `💰 Set a budget` deeplink to `config:cu` for one-tap budget setup. 5 doc files updated (schedule-tasks how-to, cost-budgets callout, troubleshooting symptom table, FAQ Q, config reference `[loop]` section). Empirically grounded — `claude --resume` does NOT restore session-scoped cron tasks in `claude` v2.1.129/2.1.132 in `--print` mode (Probe 1), so Untether owns ALL firing across both CronCreate and ScheduleWakeup tool families. 58 new tests across `tests/test_loop_scheduler.py` (41), `tests/test_claude_runner.py::TestLoopObservation` (10 + 1 sync), and `tests/test_config_command.py::TestLoopMode` (7) [#289](https://github.com/littlebearapps/untether/issues/289)
+
+### fixes
+
+- **fix:** rc13 — plan-mode research/audit completions no longer ship 25k–42k char (~8–12 Telegram message) finals. The rc11 fix for #508 (Layer A preamble + Layer E plan-body re-emit) was directionally right but tuned too verbose: A1 told Claude to "expand the bullets into a substantive summary" for research/audit tasks (plan bodies ballooned to 2–5k chars), A2 told Claude "your next assistant message MUST repeat the substantive findings" (post-approval text ballooned to 0.5–2k chars and was paraphrased rather than literal-copied), and Layer E's substring skip rule `body in final_answer` failed on every paraphrased run, so the plan body was unconditionally concatenated in front of the post-approval text. Staging `@hetz_lba1_bot` v0.35.3rc12 over 48 h showed aushistory finals at 14k / 16k / 28k / 35k / 42k chars and scout finals at 26k / 27k chars — the 42k case matches the 11-message user repro. The Telegram MCP `search_messages` literal `📋 Plan (approved):` returned hits on every recent plan-mode completion, confirming Layer E was the load-bearing over-firer rather than preamble alone. rc13 retunes both layers to CLI-style brevity: A1 becomes "concise 3–5 bullets; plan is shown for approval, not as the final deliverable" (drops the "expand into substantive summary" license); A2 becomes "brief CLI-style summary, 3–7 bullets or 1–2 short paragraphs, ~500–1500 chars, do NOT re-paste the full plan content"; A3 (`## Summary` `### Plan/Document Created`) becomes "Path AND a 3–5 bullet headline summary, not a re-paste of the full content". Layer E's `_prepend_exitplanmode_plan` substring check is replaced with a length gate (`len(final_answer) < 600`) so a real CLI-style summary skips the prepend entirely; substring check stays as a cheap belt-and-braces second skip; the plan body is capped at 1500 chars + `…\n\n(plan truncated — shown in full during approval)` when Layer E does fire (preserving the original #508 UX for genuinely-empty post-approval results without re-introducing runaway concatenation). 7 new / updated tests in `tests/test_preamble.py` (regression-locks the rc11 verbosity-driving phrases out of `_DEFAULT_PREAMBLE`, plus length-gate / body-cap / substring-skip cases) and 2 in `tests/test_claude_runner.py` (`test_translate_result_skips_prepend_when_answer_substantive`, `test_translate_result_caps_long_plan_body_when_prepending`) [#515](https://github.com/littlebearapps/untether/issues/515)
+- **fix:** rc11 — research/audit plan-mode runs no longer surface a short final Telegram message that just points to a plan file. Live user impact: 5m30s scout-project research run on staging v0.35.3rc10 produced a `result` answer of 584 chars (the brief plan-body acknowledgement extracted via the `last_assistant_text` empty-`result` fallback), with the substantive findings only available in `~/.claude/plans/<topic>.md` — unhelpful on a phone where files cannot easily be opened. Two-layer fix per gpt-5.2 + gemini-3.1-pro consensus and an advisor pass: **Layer A (preamble)** — `_DEFAULT_PREAMBLE` in `runner_bridge.py` now includes a Plan-mode requirements section instructing Claude that (A1) the `ExitPlanMode` `plan` parameter MUST contain a 3–5 bullet substantive summary, never just a file path; (A2) the post-approval next assistant message MUST repeat the substantive findings (the plan-body messages on Telegram disappear after approval, so post-approval text is the only thing the user retains); and (A3) the `### Plan/Document Created` summary bullet now asks for inline key findings, not just a path pointer. **Layer E (capture & re-emit)** — new `ClaudeStreamState.last_exitplanmode_plan` field is populated from `tool_use.input.plan` whenever Claude calls `ExitPlanMode`, captured in the `StreamToolUseBlock` arm of `translate_claude_event`. The previously-dead `_outline_prefix` matcher in `runner_bridge.handle_message` is replaced with a new `_prepend_exitplanmode_plan(final_answer, plan_body)` helper that prepends the plan body with a `📋 Plan (approved):` header + separator when the post-approval `final_answer` doesn't already contain it (substring-only gate; no length threshold — the live repro had answer_len=584, larger than any sensible threshold). Skip rule covers the case where Layer A causes Claude to repeat the plan content in its post-approval text, avoiding duplication. 8 new tests across `tests/test_preamble.py` (A1/A2/A3 clauses present + 5 `_prepend_exitplanmode_plan` cases: short final, substring-skip, no-plan, empty, None) and `tests/test_claude_runner.py` (`test_translate_exitplanmode_captures_plan_body`, `test_translate_exitplanmode_ignores_empty_plan_body`) [#508](https://github.com/littlebearapps/untether/issues/508)
+- **fix:** rc11 — `ScheduleWakeup` calls outside `/loop dynamic mode` no longer hold the Claude session alive indefinitely. Live impact: session `845cfcc3-…` on staging v0.35.3rc10 sat post-result idle for 58 minutes before manual `/cancel` (`peak_idle_seconds=3502.3`, `stall_warnings=15`) — the upstream `ScheduleWakeup` tool is documented as *only* firing under `/loop dynamic mode`, so calling it outside that mode is a silent no-op, the agent's turn ended, and Untether's `_post_result_idle_watchdog` waited the full 600 s timeout while `_has_pending_wakeup()` correctly suppressed stall auto-cancel. Fix: detect the dead-wakeup case in `ClaudeRunner._post_result_idle_watchdog` (claude.py:2406) by reading the existing `state.live_wakeups` registry (#481) plus a new parallel `state.live_wakeups_arm_delay` dict that captures the original `delaySeconds` at arm time (the deadline value in `live_wakeups` is hard to invert after it passes). When a wakeup is armed AND `_loop_enabled_for_chat(get_run_channel_id())` returns False, the watchdog cuts its effective timeout to `min(timeout_s, max_armed_delay + 60.0)` so the session closes within delay+grace instead of the default 600 s. The closing structlog `claude.post_result_idle.closing_stdin` gains `effective_timeout_s` and `dead_wakeup` keys so untether-issue-watcher can surface the new shortcut path. With `/loop` ON, the shortcut never fires — legitimate background work keeps the full default timeout. 2 new regression tests in `tests/test_claude_runner.py` (`test_dead_schedule_wakeup_shortens_post_result_timeout`, `test_active_loop_preserves_default_post_result_timeout`) [#507](https://github.com/littlebearapps/untether/issues/507)
+- **fix:** rc11 — base `JsonlSubprocessRunner._iter_jsonl_events` now breaks the read loop after a `CompletedEvent`, mirroring Claude's override (added during #502). Defensive hardening — without the break, any non-Claude engine subprocess (Codex, OpenCode, Pi, Gemini, AMP) that emits its terminal event AND has a child inheriting the stdout fd (MCP server, backgrounded shell, …) would block on `iter_json_lines` waiting for an EOF that never comes; `proc.wait()` is then never reached and the task group hangs. Not yet observed in production because Claude is the only engine known to spawn long-lived MCP children today, but the test prototyped during #502 work confirmed the bug exists in the base path. Per-engine audit (codex/opencode/pi/gemini/amp) confirmed each emits exactly one terminal event with no post-completion events, so the unconditional break is safe. 1 new regression test in `tests/test_exec_runner.py` (`test_base_iter_jsonl_breaks_on_did_emit_completed`) using a stub `iter_json_lines` that yields a `TurnCompleted` line then awaits an unfired `anyio.Event()` — without the break the test hangs past the 2 s `fail_after` deadline [#505](https://github.com/littlebearapps/untether/issues/505)
+- **fix:** Claude schema now recognises `server_tool_use` and `advisor_tool_result` content block types — Anthropic server-side tools (web_search, code_execution, computer_use, …) and the parent agent's `advisor()` meta-tool result blocks. Previously msgspec rejected the whole JSONL line with `ValidationError: Invalid value 'server_tool_use'` (or `'advisor_tool_result'`) and the runner silently dropped tool-use info — no progress action in Telegram, no entry in `state.pending_actions`, no input to verbose-mode rendering or cost tracking. Sampling 24h of staging traffic on 2026-05-08 showed paired `server_tool_use` + `advisor_tool_result` events firing across **5 different projects** (auditor-toolkit, scout, brand-copilot, aushistory) and **5 different sessions**. New msgspec structs `StreamServerToolUseBlock` (mirrors `StreamToolUseBlock`: id/name/input) and `StreamAdvisorToolResultBlock` (mirrors `StreamToolResultBlock`: tool_use_id/content/is_error) join the `StreamContentBlock` union; `translate_claude_event`'s match arm for assistant content widens to share the existing tool_use body for `server_tool_use` (`_register_background_handle` and `_observe_loop_tool_use` already filter on tool name and no-op cleanly for unrecognised server tools), and the user-message `isinstance` check widens to share the tool_result body for `advisor_tool_result`. No new helpers, no new branches — server tools render via the existing `format_verbose_detail` (web_search has a verbose handler; code_execution / computer_use fall back to `▸ <tool_name>`). 5 new tests: 3 in `tests/test_claude_schema.py` (`test_decode_server_tool_use_block`, `test_decode_advisor_tool_result_block`, `test_decode_advisor_tool_result_block_minimal`) cover schema round-trip including optional-field defaults; 2 in `tests/test_claude_runner.py` (`test_translate_server_tool_use_block`, `test_translate_advisor_tool_result_block`) cover translation, `pending_actions` lifecycle, and `last_tool_use_id` stamping [#489](https://github.com/littlebearapps/untether/issues/489)
+- **fix:** AskUserQuestion multi-question flow no longer crashes Untether with `TypeError` after answering question 1 of N via the "Other" → text-reply path. Observed live on staging (`@hetz_lba1_bot`, v0.35.2) on 2026-05-08: `route_message` constructed a `RenderedMessage` for the next question's option-button keyboard but passed it to a `send_plain` partial whose `text:` kwarg expects `str`, raising `TypeError: sequence item 0: expected str instance, RenderedMessage found` inside `markdown.assemble_markdown_parts` and propagating up to kill the entire Untether process (systemd auto-restarted in ~10s with no Telegram update loss thanks to `offset_persistence.py`, but ALL active runs across all chats were lost). Refactored: the multi-question continuation logic is now a module-level helper `send_next_ask_question_message` in `telegram/commands/ask_question.py` that calls `transport.send` directly with a `RenderedMessage` carrying HTML parse_mode + inline_keyboard. `route_message` calls the helper for the text-reply continuation path; the callback-button continuation path still edits in place via `ctx.executor.edit` (unchanged). 2 new regression tests in `tests/test_ask_user_question.py` (`test_send_next_ask_question_message_uses_rendered_message`, `test_send_next_ask_question_message_no_thread`) covering thread-aware and thread-less SendOptions [#488](https://github.com/littlebearapps/untether/issues/488)
+- **fix:** `/at`-scheduled runs now stamp `RunContext.trigger_source = "at:<token>"` so the run footer shows `⏰ at:<token>` provenance, mirroring the `⏰ cron:<id>` and `⚡ webhook:<id>` markers already added in #271 (rc4) and Tier 2/3 (rc5). Closes the gap noted in the 2026-04-25 Codex sweep comment on #271, where `/at` fires were the only trigger source whose footer was indistinguishable from a regular user-initiated run. `at_scheduler.schedule_delayed_run` now wraps the captured chat context (or a fresh `RunContext` if the chat is unmapped) with `dataclasses.replace(context, trigger_source=f"at:{token}")` after the token is generated; `runner_bridge.handle_message`'s existing icon-prefix tuple is extended from `("cron:",)` to `("cron:", "at:")` so the alarm-clock icon renders for both (semantically a one-shot delayed cron). `record_run`'s existing `triggered=bool(context and context.trigger_source)` gate also picks up `/at` runs in the `/stats` triggered/manual breakdown, no extra wiring needed. 1 new test in `tests/test_at_command.py` (`test_handle_stamps_trigger_source_on_mapped_chat`); the existing `test_handle_captures_global_default_when_unmapped` extended to assert the trigger_source-only RunContext path; the existing `test_run_delayed_forwards_captured_context_and_engine` updated since the captured context is no longer reference-equal to the original (it now carries the stamped trigger_source) [#271](https://github.com/littlebearapps/untether/issues/271)
+- **security:** auto-approve scope review for Claude `ControlRewindFilesRequest` and `ControlMcpMessageRequest` (`src/untether/runners/claude.py:_AUTO_APPROVE_TYPES`). Both subtypes were verified safe under the present upstream Claude Code 2.1.x trust model: Untether is a transport pass-through that never inspects the `mcp_message.message` payload (a compromised MCP server is the inherent MCP threat model, not specific to auto-approve), and `rewind_files` is user-initiated upstream (the model cannot trigger it autonomously) and does not touch Untether's per-session approval state (`_PLAN_EXIT_APPROVED`, `_DISCUSS_APPROVED`). Added a multi-paragraph safety-invariant comment near the auto-approve gate documenting the re-audit trigger (upstream semantic change to either subtype) plus 3 regression-lock tests in `tests/test_claude_control.py::TestAutoApproveSafetyInvariant` that fail loudly if the auto-approve path starts inspecting payloads. Audit memo: `docs/audits/2026-04-27-380-auto-approve-scope-review.md` [#380](https://github.com/littlebearapps/untether/issues/380)
+- **security:** `voice_transcription_api_key` is now `SecretStr` (parity with `bot_token` from #196). The value is masked in `repr()`/`str()`/tracebacks and any accidental structlog serialisation. Access goes via `.get_secret_value()` at the sole transport boundary in `telegram/loop.py:2208` before passing to the OpenAI SDK; everything in between (`TelegramBridgeConfig.update_from`, hot-reload) handles `SecretStr | None` end-to-end. Empty / whitespace-only configured values round-trip to `None` to preserve the prior `NonEmptyStr | None` contract [#378](https://github.com/littlebearapps/untether/issues/378)
+- **security:** daily cost tracker no longer loses updates under concurrent calls. `cost_tracker._daily_cost` previously did an unguarded read-modify-write — two concurrent `record_run_cost` calls could both read `(today, X)`, both write `(today, X + cost)`, and lose one run's cost. Under attack this defeats the per-day budget gate. Wrapped the RMW in a `threading.Lock`; `get_daily_cost()` also acquires the lock for snapshot consistency. Functions stay synchronous — the critical section is a single tuple assignment (sub-microsecond) and `threading.Lock` covers both async (cooperative) and threaded callers. New `ThreadPoolExecutor`-based fuzz test (16 workers × 200 calls) asserts atomicity [#379](https://github.com/littlebearapps/untether/issues/379)
+- **security:** prompt content moved out of INFO logs. The `runner.start` log used to carry `prompt=<first 100 chars>`. Prompts can contain credentials, PII, or proprietary code; INFO logs are typically the most broadly-accessible tier. `runner.start` now keeps `prompt_len` and `args` only; a new `runner.start_prompt` event at DEBUG carries the preview when explicitly opted in [#205](https://github.com/littlebearapps/untether/issues/205)
+- **security:** Claude runner override of `runner.start` no longer leaks prompt content at INFO. `runners/claude.py:run_impl` had its own duplicate `runner.start` call that was missed when the base runner was fixed for #205 — it kept emitting `prompt=prompt[:100] + "…"` for every Claude session. Five live runs during the v0.35.3 follow-up E2E pass confirmed it leaked the first ~100 chars of the Untether preamble at INFO; not user content in practice, but spec violation. The override now mirrors the base impl: `prompt_len` + `args` at INFO, `runner.start_prompt` preview at DEBUG. Argv redaction tightened too — `redact_env_i_args` strips `env -i KEY=VAL` pairs (#361 was already doing this for `subprocess.spawn` but not for `runner.start`), and legacy-mode (no `permission_mode`) argv has the trailing `-- <prompt>` collapsed to `-- <prompt redacted>` so prompt content never reaches INFO under any code path. 2 new regression tests in `tests/test_claude_runner.py` (`test_runner_start_does_not_log_prompt_at_info` covering control-channel mode, `test_runner_start_redacts_legacy_mode_prompt_in_args` covering legacy `-p` mode) [#478](https://github.com/littlebearapps/untether/issues/478)
+- **security:** AMP runner default flipped — `dangerously_allow_all` is now `False` by default, requiring an explicit `[amp] dangerously_allow_all = true` to opt in. Previously, AMP runs ran with no permission controls unless the operator went out of their way to disable them — backwards from how every other engine ships. Untether's own permission layer remains the primary control; AMP's permission system is a defence-in-depth that's now on by default [#206](https://github.com/littlebearapps/untether/issues/206)
+- **security:** Pi session directories are created with explicit `0o700` mode and any pre-existing dir gets `chmod`'d to `0o700` so other users on shared hosts can't read Pi session JSONL [#207](https://github.com/littlebearapps/untether/issues/207)
+- **security:** `_sanitise_stderr` regex extended to cover macOS (`/Users/<user>/`, `/private/var/...`), container roots (`/app/`, `/workspace/`), and other absolute paths beyond `/home/<user>/` (`/var/`, `/tmp/`, `/opt/`, `/srv/`, `/etc/`, `/usr/local/`, `/root/`). Path:line markers (`:42`) survive sanitisation so stack traces remain useful [#208](https://github.com/littlebearapps/untether/issues/208)
+- **security:** `/file get` no longer has a TOCTOU window between `stat()` and `read_bytes()`. The download path now opens the file once and reads at most `max_download_bytes + 1` bytes inside an `anyio.to_thread.run_sync` worker so a file that grows mid-read can't slip past the cap. Also keeps the event loop unblocked on slow disks [#211](https://github.com/littlebearapps/untether/issues/211)
+- **security:** structlog token redaction now covers OpenAI project keys (`sk-proj-...`). The generic `sk-...` regex didn't match the project-key char set (underscore + hyphen). Added a dedicated `OPENAI_PROJECT_KEY_RE` applied before the generic pattern [#213](https://github.com/littlebearapps/untether/issues/213)
+- **security:** Pygments bumped 2.19.2 → 2.20.0 to clear CVE-2026-4539 (ReDoS in `AdlLexer`). Transitive dep — `uv lock --upgrade-package pygments` plus an `--ignore-vuln CVE-2026-4539` removal in CI's `pip-audit` step [#402](https://github.com/littlebearapps/untether/issues/402)
+- **security(secrets):** placeholder bot-token strings replaced with `<BOT_ID>:<BOT_TOKEN>` in user-facing onboarding text and tutorials (`telegram/onboarding.py`, `docs/tutorials/install.md`, `llms-full.txt`) so the GitHub secret-scanner stops flagging the format. Test fixtures kept as-is — operator dismisses those alerts as "used in tests" [#403](https://github.com/littlebearapps/untether/issues/403)
+- **fix:** Claude post-result idle no longer emits stall noise + adds a clean closing message. After Claude emits a `result` event, `_post_result_idle_watchdog` (#333) keeps stdin open for `[watchdog] post_result_idle_timeout` (default 600 s) so multi-turn sessions don't pay a respawn cost; previously the existing stall monitor would still tick during that window and surface "no progress for 10 min" warnings — pure noise to the user, since the watchdog was the legitimate owner of the silence. Now (a) `progress_edits.stall_post_result_suppressed` fires while the watchdog runs, (b) the auto-cancel `_STALL_MAX_WARNINGS` arm is also gated (so a session about to gracefully close cannot be SIGTERM'd), and (c) when the watchdog actually closes stdin it stamps `ClaudeStreamState.post_result_closed_at` + `post_result_idle_minutes`, which the bridge's heartbeat tick polls and uses to fire one (and only one) Telegram message: `✓ turn complete · session closed after Nm idle` — gives the user a clean end-state signal instead of inferring from silence. Idempotency is enforced via a `post_result_closing_sent` flag; structlog WARN events are unchanged so `untether-issue-watcher` continues to see them. Genuinely-frozen post-result sessions (frozen-ring escalation) still warn — the suppression is precisely scoped, not a blanket disable. 4 new tests in `tests/test_exec_bridge.py` (`test_stall_post_result_suppressed_when_result_armed`, `test_stall_post_result_blocks_auto_cancel`, `test_stall_post_result_overridden_by_frozen_ring`, `test_post_result_closing_message_sent`, `test_post_result_closing_message_idempotent`) [#470](https://github.com/littlebearapps/untether/issues/470)
+- **fix:** ScheduleWakeup deadline was always 0.0 in production. `_register_background_handle` in `runners/claude.py` read `delay_ms`/`timeout_ms` from the tool input, but the actual Claude Code stream-json schema (per #289 and the upstream `claude-agent-sdk-python` reference) emits `delaySeconds` (range 60–3600). `live_wakeups[tool_id]` membership-only checks (`#346` wedge detector) still worked because both branches populated the dict; deadlines fell to 0.0, breaking countdown rendering. Fixed by reading `delaySeconds` first and keeping the `delay_ms`/`timeout_ms` fallbacks for backward compat with existing test fixtures. Necessary precursor to #481's countdown rendering. 2 new regression tests in `tests/test_claude_runner.py` (`test_schedule_wakeup_reads_delaySeconds_field`, `test_schedule_wakeup_delay_ms_fallback_still_works`) [#481](https://github.com/littlebearapps/untether/issues/481)
+
+### docs
+
+- **docs:** new `docs/faq/faq.md` (originally landed as `docs/faq/index.md` in rc6; renamed in rc9 [#483](https://github.com/littlebearapps/untether/issues/483) so the help-centre URL is `/help/untether/faq/` rather than `/help/untether/index/`) with 12 H2 question-shaped FAQs covering install, supported engines, API keys, data flow, interactive approvals, crash recovery, cost budgets, voice notes, update, uninstall, and support channels. Sourced from README + real common-channel topics; no placeholders. Companion to the marketing-site FAQPage Schema.org pipeline shipped on `feature/help-seo-geo-items-1-4` in `littlebearapps/littlebearapps.com` — the docs-sync mapping (`scripts/docs-sync.config.ts`) lands separately on the marketing-site repo. Once both PRs merge, `https://untether.littlebearapps.com/help/untether/faq/` will surface a `<script type="application/ld+json">` `FAQPage` block with all 12 Q/A pairs for AI-citation surface (ChatGPT, Perplexity, Google AI Overviews) and SERP rich-snippet eligibility [#477](https://github.com/littlebearapps/untether/issues/477)
+- **docs:** new `## Loop mode` section in `docs/how-to/schedule-tasks.md` explaining the observe-and-fire-on-resume architecture, runaway caps, and per-fire cost ranges (cache-warm vs cold). Cost-budgets how-to gets a Loop-mode + budgets warning callout. Troubleshooting how-to gets a "Loop didn't fire / loop fired too many times" symptom table. FAQ gets a new H2 "Does /loop work via Untether?" (verifies against `.claude/rules/help-faq.md`: 13 H2s, all question-shaped). Config reference gets a new `[loop]` section between `[watchdog]` and `[auto_continue]` with the explicit "cost limits are NOT in `[loop]`" pointer to `[cost_budget]` [#289](https://github.com/littlebearapps/untether/issues/289)
+
 ## v0.35.2 (2026-04-20)
 
 ### changes
diff --git a/CLAUDE.md b/CLAUDE.md
index 07fc0d9b..34871246 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -13,6 +13,7 @@ Untether adds interactive permission control, plan mode support, and several UX
 - **Pause & Outline Plan** — third button on plan approval; after Claude writes the outline, Approve/Deny/Let's discuss buttons appear automatically (hold-open keeps session alive while user reads)
 - **Agent context preamble** — configurable prompt preamble tells agents they're on Telegram and requests structured end-of-task summaries; `[preamble]` config section
 - **`/planmode`** — toggle permission mode per chat (on/off/auto)
+- **`/listen`** — set listen mode (`all` / `mentions`) per chat or topic; controls when the bot responds in groups; renamed from `/trigger` in v0.35.3 (#297) to disambiguate from webhook/cron triggers — `/trigger` still works as a deprecated alias for one release cycle
 - **Ask mode** — interactive AskUserQuestion with option buttons, sequential multi-question flows, and `/config` toggle; Claude-only
 - **Early callback answering** — clears button spinners immediately instead of waiting for processing
 - **Approval push notifications** — separate notify message when approval buttons appear
@@ -47,6 +48,8 @@ Untether adds interactive permission control, plan mode support, and several UX
 - **Trigger visibility (Tier 1)** — `/ping` shows per-chat trigger summary (`⏰ triggers: 1 cron (id, 9:00 AM daily (Melbourne))`); run footer shows `⏰ cron:<id>` / `⚡ webhook:<id>` for trigger-initiated runs; new `describe_cron()` utility renders common patterns in plain English
 - **Graceful restart improvements (Tier 1)** — persists Telegram `update_id` to `last_update_id.json` so restarts don't drop/duplicate messages; `Type=notify` systemd integration via stdlib `sd_notify` (`READY=1` + `STOPPING=1`); `RestartSec=2`
 - **`diff_preview` plan bypass (#283)** — after user approves a plan outline via "Pause & Outline Plan", the `_discuss_approved` flag short-circuits diff preview for subsequent Edit/Write tools so no second approval is needed
+- **User-extensible env allowlist (#409)** — `[security] env_extra_allow` and `env_extra_prefix_allow` (in `untether.toml`) extend the engine-subprocess env allowlist with per-deployment names so users can thread credential-manager tokens (1Password, Doppler, Vault, Infisical, …) without forking `utils/env_policy.py`. Names are validated against `[A-Z_][A-Z0-9_]*`. Honoured by the Claude and Pi runners and by the `env_audit` probe. `BWS_ACCESS_TOKEN` was promoted into the built-in defaults at the same time. One `env_policy.user_extension` INFO log per process
+- **Master trigger pause toggle (#294)** — `TriggerManager.pause()` / `resume()` / `is_paused` gate cron firing and webhook dispatch globally; webhook server returns `503 triggers paused` (with `Retry-After: 60`); `/health` endpoint reflects paused state. Wired into `/config` two ways: home-page button row (only when triggers configured) and a dedicated `📡 Triggers` page (`config:tg`) showing counts + Pause/Resume button. `/ping` switches to `⏸ triggers paused: … (suspended)` while paused. Pause is in-memory only — restart auto-resumes (safe default)
 
 See `.claude/skills/claude-stream-json/` and `.claude/rules/control-channel.md` for implementation details.
 
@@ -84,6 +87,8 @@ Telegram <-> TelegramPresenter <-> RunnerBridge <-> Runner (claude/codex/opencod
 | `commands/config.py` | `/config` inline settings menu |
 | `commands/ask_question.py` | AskUserQuestion option button handler |
 | `commands/topics.py` | `/new`, `/ctx`, `/topic` commands; `_cancel_chat_tasks()` helper |
+| `commands/listen.py` | `/listen` command (listen-mode toggle); `/trigger` deprecated alias (#297) |
+| `listen_mode.py` | `resolve_listen_mode()` and `should_trigger_run()` for response gating |
 | `utils/proc_diag.py` | `/proc` process diagnostics for stall analysis (CPU, RSS, TCP, FDs, children) |
 | `shutdown.py` | Graceful shutdown state and drain logic |
 | `telegram/bridge.py` | Telegram message rendering |
@@ -156,8 +161,9 @@ Project hooks in `.claude/hooks.json` fire automatically:
 | Hook | Trigger | What it does |
 |------|---------|-------------|
 | release-guard | Bash: `git push`, `git tag`, `gh pr merge`, `gh release` | Blocks pushes to master/main, tag creation, PR merging, releases; allows feature and dev branch pushes |
-| release-guard-protect | Edit/Write to guard scripts or `hooks.json` | Prevents modification of release guard infrastructure |
+| release-guard-protect | Edit/Write to guard scripts, `hooks.json`, or `help-faq-protect.sh` | Prevents modification of release guard infrastructure and the FAQ-protect hook |
 | release-guard-mcp | GitHub MCP write tools | Blocks `merge_pull_request` and writes to master/main; allows feature branches |
+| help-faq-protect | Bash: `rm`, `git rm`, `mv`, `>` redirect targeting `docs/faq/faq.md` | Blocks deletion / move / truncate of the help-centre FAQ; edits via Edit/Write/append `>>` are allowed (#477, #483) |
 | dev-workflow-guard | `systemctl` with `untether` | Blocks staging restarts during dev; guides to `untether-dev`; allows `staging.sh`/`pipx upgrade` path |
 | runner-edit-context | Edit/Write to `runners/*.py` | 3-event contract, PTY lifecycle, test/doc reminders |
 | schema-edit-context | Edit/Write to `schemas/*.py` | msgspec impact on parsing, fixture updates |
@@ -177,6 +183,7 @@ Rules in `.claude/rules/` auto-load when editing matching files:
 | `release-discipline.md` | `CHANGELOG.md`, `pyproject.toml` | GitHub issue linking, changelog format, semantic versioning |
 | `dev-workflow.md` | `src/untether/**` | Dev vs staging separation, never restart staging for testing, always use untether-dev |
 | `context-quality.md` | AI context files (`CLAUDE.md`, `AGENTS.md`, etc.) | Cross-file consistency, path verification, version accuracy, command accuracy |
+| `help-faq.md` | `docs/faq/**` | NEVER delete; keep FAQ current with feature changes; H2s must be question-shaped (#477) |
 
 ## Tests
 
@@ -200,7 +207,7 @@ Key test files:
 - `test_cooldown_bypass.py` — 21 tests: outline bypass, rapid retry auto-deny, no-text auto-deny, cooldown escalation, hold-open outline flow
 - `test_verbose_progress.py` — 21 tests: format_verbose_detail() for each tool type, MarkdownFormatter verbose mode, compact regression
 - `test_verbose_command.py` — 7 tests: /verbose toggle on/off/clear, backend id
-- `test_config_command.py` — 218 tests: home page, plan mode/ask mode/verbose/engine/trigger/model/reasoning sub-pages, toggle actions, callback vs command routing, button layout, engine-aware visibility, default resolution
+- `test_config_command.py` — 221 tests: home page, plan mode/ask mode/verbose/engine/listen/model/reasoning sub-pages, toggle actions, callback vs command routing, button layout, engine-aware visibility, default resolution
 - `test_pi_compaction.py` — 6 tests: compaction start/end, aborted, no tokens, sequence
 - `test_proc_diag.py` — 24 tests: format_diag, is_cpu_active, collect_proc_diag (Linux /proc reads), ProcessDiag defaults
 - `test_exec_runner.py` — 22 tests: event tracking (event_count, recent_events ring buffer, PID in StartedEvent meta), JsonlStreamState defaults
@@ -374,6 +381,12 @@ Before tagging a release:
 
 48 screenshots in `docs/assets/screenshots/` with a tracking checklist in `CAPTURES.md`. README uses a composite hero collage (`hero-collage.jpg`) built with ImageMagick for mobile responsiveness. Doc files use HTML `<img>` tags with `width="360"` and `loading="lazy"` (works in both GitHub and MkDocs). 14 screenshots are still missing and commented out with `<!-- TODO: capture screenshot -->` markers.
 
+## Help-centre FAQ
+
+`docs/faq/faq.md` (12 H2 question-shaped Q/A pairs; renamed from `docs/faq/index.md` in #483 so the help-centre URL becomes `/help/untether/faq/`) backs the marketing-site **FAQPage Schema.org** pipeline shipped on `feature/help-seo-geo-items-1-4` in [`littlebearapps/littlebearapps.com`](https://github.com/littlebearapps/littlebearapps.com). Once the docs-sync mapping in `scripts/docs-sync.config.ts` registers `untether → docs/faq → category: faq`, the marketing site emits `<script type="application/ld+json">` `FAQPage` JSON-LD on every help-centre deploy, unlocking AI-citation surface (ChatGPT, Perplexity, Google AI Overviews) and SERP rich-snippet eligibility.
+
+**The file MUST NOT be deleted or moved** — that silently breaks the docs-sync mapping and regresses the schema on the next deploy. The repo enforces this via the `help-faq-protect.sh` Bash hook which blocks `rm`, `git rm`, `mv`-away, and shell `>` truncation. **Edits ARE encouraged**: keep the FAQ in sync with new features as they land in `CHANGELOG.md`. See [`.claude/rules/help-faq.md`](.claude/rules/help-faq.md) for the full update cadence and shape rules. Tracking issues: [#477](https://github.com/littlebearapps/untether/issues/477) (creation), [#483](https://github.com/littlebearapps/untether/issues/483) (URL rename).
+
 ## Conventions
 
 - Python 3.12+, anyio for async, msgspec for JSONL parsing, structlog for logging
diff --git a/README.md b/README.md
index c7f9813d..92e2b27f 100644
--- a/README.md
+++ b/README.md
@@ -97,11 +97,12 @@ The wizard offers three **workflow modes** — pick the one that fits:
 - 🔄 **Cross-environment resume** — start a session in your terminal, pick it up from Telegram with `/continue`; works with Claude Code, Codex, OpenCode, Pi, and Gemini ([guide](docs/how-to/cross-environment-resume.md))
 - 📎 **File transfer** — upload files to your repo with `/file put`, download with `/file get`; agents can also deliver files automatically by writing to `.untether-outbox/` during a run — sent as Telegram documents on completion
 - 🛡️ **Graceful recovery** — orphan progress messages cleaned up on restart; stall detection with CPU-aware diagnostics; auto-continue for Claude Code sessions that exit prematurely
-- ⏰ **Scheduled tasks** — cron expressions with timezone support, webhook triggers, one-shot delays (`/at 30m <prompt>`), `run_once` crons, and hot-reload configuration (no restart required). `/ping` shows per-chat trigger summary; trigger-initiated runs show provenance in the footer
+- ⏰ **Scheduled tasks** — cron expressions with timezone support, webhook triggers, one-shot delays (`/at 30m <prompt>`), `run_once` crons, master pause/resume toggle, and hot-reload configuration (no restart required). `/ping` shows per-chat trigger summary; trigger-initiated runs show provenance in the footer (`⏰ cron:<id>` / `⚡ webhook:<id>` / `⏰ at:<token>`); `/stats` reports per-engine triggered-vs-manual breakdown
+- 🔁 **Autonomous loops (Claude only)** — opt-in observation of Claude Code's `/loop` and `ScheduleWakeup`; Untether re-fires iterations after the subprocess exits so loops keep running between turns. Off by default; enable per chat via `/config → 🔁 Loop mode`. Cost guarded by `[cost_budget]`, runaway-safety capped by `[loop]` (max iterations, total duration, expiry)
 - 💬 **Forum topics** — map Telegram topics to projects and branches
 - 📤 **Session export** — `/export` for markdown or JSON transcripts
 - 🗂️ **File browser** — `/browse` to navigate project files with inline buttons
-- ⚙️ **Inline settings** — `/config` opens an in-place settings menu; toggle plan mode, ask mode, approval policy (Codex), approval mode (Gemini), verbose, engine, model, reasoning, and trigger with buttons
+- ⚙️ **Inline settings** — `/config` opens an in-place settings menu; toggle plan mode, ask mode, approval policy (Codex), approval mode (Gemini), verbose, engine, model, reasoning, and listen mode with buttons; dedicated `📡 Triggers` page lists per-chat crons/webhooks with last-fired times and a master pause/resume toggle
 - 🧩 **Plugin system** — extend with custom engines, transports, and commands
 - 🔌 **Plugin-compatible** — Claude Code plugins detect Untether sessions via `UNTETHER_SESSION` env var, preventing hooks from interfering with Telegram output; works with [PitchDocs](https://github.com/littlebearapps/lba-plugins) and other Claude Code plugins
 - 📊 **Session statistics** — `/stats` shows per-engine run counts, action totals, and duration across today, this week, and all time
@@ -168,7 +169,7 @@ Claude effort levels: `low`, `medium`, `high`, `xhigh`, `max` (`xhigh` requires
 | `/agent` | Show or set the engine for this chat |
 | `/model` | Override the model for an engine |
 | `/planmode` | Toggle plan mode (on/auto/off) |
-| `/usage` | Show API costs for the current session |
+| `/usage` | Show API costs for the current session (`/usage debug` shows fetch state, OAuth expiry, schema-mismatch counter) |
 | `/export` | Export session transcript |
 | `/browse` | Browse project files |
 | `/new` | Cancel running tasks and clear stored sessions |
@@ -177,10 +178,10 @@ Claude effort levels: `low`, `medium`, `high`, `xhigh`, `max` (`xhigh` requires
 | `/topic` | Create or bind forum topics |
 | `/restart` | Gracefully restart Untether (drains active runs first) |
 | `/verbose` | Toggle verbose progress mode (show tool details) |
-| `/config` | Interactive settings menu (plan mode, ask mode, verbose, engine, model, reasoning, trigger, approval mode, cost & usage) |
+| `/config` | Interactive settings menu (plan mode, ask mode, verbose, engine, model, reasoning, listen, approval mode, cost & usage); `📡 Triggers` page for cron/webhook list + master pause/resume |
 | `/ctx` | Show or update project/branch context |
 | `/reasoning` | Set reasoning level override |
-| `/trigger` | Set group chat trigger mode |
+| `/listen` | Set group chat listen mode (`all` / `mentions` / `clear`); `/trigger` still works as a deprecated alias |
 | `/stats` | Per-engine session statistics (today/week/all-time) |
 | `/auth` | Codex device re-authentication |
 | `/at 30m <prompt>` | Schedule a one-shot delayed run (60s–24h; `/cancel` to drop) |
@@ -275,7 +276,7 @@ Full documentation is available in the [`docs/`](https://github.com/littlebearap
 - [File browser](https://github.com/littlebearapps/untether/blob/master/docs/how-to/browse-files.md) — `/browse` inline navigation
 - [Session export](https://github.com/littlebearapps/untether/blob/master/docs/how-to/export-sessions.md) — markdown and JSON transcripts
 - [Verbose progress](https://github.com/littlebearapps/untether/blob/master/docs/how-to/verbose-progress.md) — tool detail display
-- [Group chats](https://github.com/littlebearapps/untether/blob/master/docs/how-to/group-chat.md) — multi-user and trigger modes
+- [Group chats](https://github.com/littlebearapps/untether/blob/master/docs/how-to/group-chat.md) — multi-user and listen modes
 - [Context binding](https://github.com/littlebearapps/untether/blob/master/docs/how-to/context-binding.md) — per-chat project/branch binding
 - [Webhooks and cron](https://github.com/littlebearapps/untether/blob/master/docs/how-to/webhooks-and-cron.md) — automated runs from external events
 - [Update Untether](https://github.com/littlebearapps/untether/blob/master/docs/how-to/update.md) — upgrade to the latest version
@@ -337,6 +338,13 @@ Untether is a fork of [takopi](https://github.com/banteg/takopi) by [@banteg](ht
 
 ---
 
+## ✍️ From the blog
+
+- <a href="https://littlebearapps.com/blog/coding-from-the-park/" target="_blank" rel="noopener noreferrer">Coding from the park</a> — why Untether exists, and what it feels like to run an agent while you're away from your desk
+- <a href="https://littlebearapps.com/blog/dogfooding-bugs-tests-cant-find/" target="_blank" rel="noopener noreferrer">Dogfooding bugs tests can't find</a> — how integration testing via `@untether_dev_bot` catches the things unit tests miss
+
+---
+
 ## 📄 Licence
 
 [MIT](https://github.com/littlebearapps/untether/blob/master/LICENSE) — Made by [Little Bear Apps](https://github.com/littlebearapps) 🐶
diff --git a/SECURITY.md b/SECURITY.md
index d92d36d7..f62155e7 100644
--- a/SECURITY.md
+++ b/SECURITY.md
@@ -45,6 +45,25 @@ Include:
 - Bot token management — token security is the operator's responsibility
 - Issues requiring physical access to the host machine
 
+## Security improvements in v0.35.3
+
+v0.35.3 ships a follow-on hardening bundle on top of v0.35.2. Upgrade notes:
+
+- **BREAKING — empty `allowed_user_ids` rejected at startup** ([#377](https://github.com/littlebearapps/untether/issues/377)). Previously the empty default meant any Telegram user who knew the bot username could send commands. Untether now refuses to start with `ConfigError: [transports.telegram] allowed_user_ids is empty …`. Operators who genuinely need an open bot (demos, hackathons, dev) must opt in explicitly with `allow_any_user = true`, which is logged INFO every boot (`security.allow_any_user`). See [Security how-to](docs/how-to/security.md).
+- **AMP `dangerously_allow_all` default flipped to `false`** ([#206](https://github.com/littlebearapps/untether/issues/206)). AMP runs no longer skip its built-in permission system unless the operator opts in.
+- **Pi session directory locked to `0o700`** ([#207](https://github.com/littlebearapps/untether/issues/207)). Other users on shared hosts can no longer read Pi session JSONL.
+- **`voice_transcription_api_key` is now `SecretStr`** ([#378](https://github.com/littlebearapps/untether/issues/378)) — parity with `bot_token`. Masked in repr/str/tracebacks and structlog serialisation.
+- **Prompt content removed from INFO logs** ([#205](https://github.com/littlebearapps/untether/issues/205), [#478](https://github.com/littlebearapps/untether/issues/478)) — `runner.start` no longer carries `prompt[:100]`. A debug-only `runner.start_prompt` event is available when explicitly enabled.
+- **`/file get` TOCTOU window closed** ([#211](https://github.com/littlebearapps/untether/issues/211)) — single-open + bounded read in a worker thread.
+- **stderr sanitisation regex extended** ([#208](https://github.com/littlebearapps/untether/issues/208)) — covers macOS (`/Users/…`, `/private/var/…`), container roots (`/app/`, `/workspace/`), and other absolute paths beyond `/home/<user>/`.
+- **OpenAI project-key redaction** ([#213](https://github.com/littlebearapps/untether/issues/213)) — structlog redaction now covers `sk-proj-…` keys (the generic `sk-…` regex didn't match the project-key char set).
+- **Daily cost tracker race fixed** ([#379](https://github.com/littlebearapps/untether/issues/379)) — the unguarded read-modify-write that could lose a run's cost (and bypass the per-day budget cap) is now wrapped in a lock.
+- **Pygments bumped 2.19.2 → 2.20.0** ([#402](https://github.com/littlebearapps/untether/issues/402)) — clears CVE-2026-4539 (ReDoS in `AdlLexer`).
+- **Auto-approve scope re-audit** ([#380](https://github.com/littlebearapps/untether/issues/380)) — `ControlRewindFilesRequest` and `ControlMcpMessageRequest` re-verified safe under the upstream Claude Code 2.1.x trust model. Regression-lock tests fail loudly if the auto-approve path starts inspecting payloads. Audit memo at `docs/audits/2026-04-27-380-auto-approve-scope-review.md`.
+- **User-extensible env allowlist** ([#409](https://github.com/littlebearapps/untether/issues/409)) — `[security] env_extra_allow` and `env_extra_prefix_allow` let operators thread credential-manager tokens (1Password, Doppler, Vault, Infisical) into engine subprocesses without forking. `BWS_ACCESS_TOKEN` is now in the built-in defaults.
+
+See [CHANGELOG v0.35.3](https://github.com/littlebearapps/untether/blob/master/CHANGELOG.md#v0353) for the full entry list.
+
 ## Security improvements in v0.35.2
 
 v0.35.2 ships a security hardening bundle. Upgrade notes:
diff --git a/docs/audits/2026-04-27-380-auto-approve-scope-review.md b/docs/audits/2026-04-27-380-auto-approve-scope-review.md
new file mode 100644
index 00000000..fcc77e72
--- /dev/null
+++ b/docs/audits/2026-04-27-380-auto-approve-scope-review.md
@@ -0,0 +1,164 @@
+# #380 — Auto-approve scope review for `ControlRewindFilesRequest` and `ControlMcpMessageRequest`
+
+**Audit date:** 2026-04-27
+**Author:** Claude (Untether agent, supervised by @npschram)
+**Issue:** [#380](https://github.com/littlebearapps/untether/issues/380)
+**Cross-ref:** [Audit 2026-04-20 §ASI02](./agent-orchestration-security-audit-2026-04-20.md), `[security] priority: high`
+
+## Scope
+
+`src/untether/runners/claude.py` auto-approves five non-tool control_request subtypes
+without surfacing them to the Telegram user:
+
+```python
+_AUTO_APPROVE_TYPES = (
+    ControlInitializeRequest,    # protocol housekeeping
+    ControlHookCallbackRequest,  # hook plumbing
+    ControlMcpMessageRequest,    # ← reviewed here
+    ControlRewindFilesRequest,   # ← reviewed here
+    ControlInterruptRequest,     # cancel
+)
+```
+
+The 2026-04-20 audit flagged the two MCP-/rewind-related types as worth a deeper
+look because:
+
+- `ControlRewindFilesRequest` could in principle undo state that drove a prior
+  denial decision.
+- `ControlMcpMessageRequest` could carry tainted payloads from a compromised
+  MCP server.
+
+This memo documents the audit findings and the regression locks added to keep
+the audit honest.
+
+## Methodology
+
+1. Read the message-shape definitions in `src/untether/schemas/claude.py:154-174`.
+2. Trace every call site in `src/untether/runners/claude.py` that handles each
+   subtype.
+3. Cross-reference Untether's session-level approval state
+   (`_PLAN_EXIT_APPROVED`, `_DISCUSS_APPROVED`, `_HANDLED_REQUESTS`) to confirm
+   nothing in the auto-approve path mutates those registries.
+4. Confirm Claude Code's upstream invocation surface for each subtype.
+
+## Findings
+
+### `ControlMcpMessageRequest` — auto-approve **safe**
+
+**Shape:** `{server_name: str, message: Any}` (subtype `"mcp_message"`).
+
+**Behaviour at the auto-approve path:**
+
+- Untether stores the request_id in `state.auto_approve_queue` and the raw
+  payload in `_REQUEST_TO_INPUT[request_id]`.
+- The payload is **never inspected, executed, parsed, or rendered** by Untether.
+  The drain task (`_drain_auto_approve`) only reads the request_id; the payload
+  is opaque storage so that an `updated_input` round-trip would be possible if
+  the protocol ever requires it (it currently doesn't for this subtype).
+- The drain emits a `control_response{approved: true}` over the stdin PTY back
+  to Claude Code.
+
+**Threat model considered:**
+
+A compromised MCP server could craft `message` to contain prompt-injection
+content. That payload would flow through Claude Code to the model. Routing
+this control_request through Telegram approval would NOT block the payload —
+the payload is already in flight to Claude Code by the time we see the
+control_request, and Claude Code is the path of record for delivering MCP
+messages to the model regardless of our acknowledgement.
+
+The risk of compromised MCP servers is the inherent threat model of any MCP
+server, not specific to auto-approve. The mitigation lives upstream (in
+Claude Code's MCP hardening work, e.g. `system.init` connection-status
+filtering and #365 catalog refresh) — not on Untether's approval channel.
+
+**Verdict:** auto-approve is correct.
+
+### `ControlRewindFilesRequest` — auto-approve **safe**
+
+**Shape:** `{user_message_id: str}` (subtype `"rewind_files"`).
+
+**Behaviour at the auto-approve path:** identical pass-through pattern as
+mcp_message — request_id queued, payload opaque, response written verbatim.
+
+**Threat model considered:**
+
+The intuitive concern is "rewind could undo state that drove a prior denial."
+Specifically: a prior turn might have included a denial that prevented a write;
+rewind to a checkpoint before that denial could let the model re-attempt and
+succeed.
+
+Three things mitigate this in practice:
+
+1. **Rewind is user-initiated.** Upstream Claude Code 2.1.x exposes rewind via
+   the `/rewind` slash command (or programmatic equivalent). The model cannot
+   autonomously trigger it. Untether currently has no UI that issues `/rewind`,
+   so this control_request only fires when the user types `/rewind` themselves
+   in a chat. The user has already consented.
+2. **Approval state does not live in the file system.** Untether's per-session
+   approval state — `_PLAN_EXIT_APPROVED`, `_DISCUSS_APPROVED`, denial counts,
+   discuss cooldowns — lives in Untether-owned module-level dicts on the
+   parent process. `rewind_files` operates on Claude Code's internal file
+   checkpoints; it does not touch Untether registries.
+3. **A subsequent write would still pass through the standard tool gate.**
+   Even if rewind reset the file state, the next write tool call would emit
+   a fresh `ControlCanUseToolRequest`, which goes through Untether's normal
+   approval flow (with diff_preview when configured). The user would see the
+   write and have a chance to deny again.
+
+**Verdict:** auto-approve is correct **as long as rewind remains
+user-initiated upstream**. If a future Claude Code release allows the model
+to trigger rewind autonomously, this audit must be revisited and rewind moved
+to `_TOOLS_REQUIRING_APPROVAL`.
+
+## Documentation + regression locks
+
+- **Inline comment** added to `src/untether/runners/claude.py` near
+  `_AUTO_APPROVE_TYPES` documenting both subtypes' invariants and the
+  re-audit trigger (upstream semantic change to either subtype).
+- **Three regression-lock tests** added to
+  `tests/test_claude_control.py::TestAutoApproveSafetyInvariant`:
+  - `test_mcp_message_payload_not_inspected` — asserts the auto-approve path
+    does not stringify, iterate, or otherwise interact with the `message`
+    payload (defence against drift toward inspecting payloads here, which
+    would mean the trust model has shifted).
+  - `test_rewind_files_request_does_not_clear_plan_approval` — asserts that
+    handling a `rewind_files` request leaves `_PLAN_EXIT_APPROVED` and
+    `_DISCUSS_APPROVED` untouched. Prevents a future change from
+    accidentally coupling rewind to per-session approval state.
+  - `test_auto_approve_emits_no_telegram_events` — asserts all five
+    auto-approve subtypes emit `[]`, the invariant that justifies skipping
+    the Telegram-side gate.
+
+## Recommendations
+
+1. **No code change beyond comment + tests.** The current auto-approve list is
+   correct under the present trust model.
+2. **Re-audit trigger.** Subscribe to upstream Claude Code release notes for
+   any semantic change to either subtype. Specifically watch for:
+   - `mcp_message` gaining the ability to carry executable instructions
+     interpreted by Claude Code itself (e.g. local CLI side effects from MCP
+     server messages).
+   - `rewind_files` becoming model-callable (e.g. via a new `Rewind` tool or
+     a model-initiated subtype).
+   The inline comment in `runners/claude.py` and this memo together form the
+   audit trail; the regression tests fail loudly if the auto-approve path
+   starts behaving differently.
+3. **Follow-up scope.** A broader audit of Claude Code's parent-initiated
+   control_request surface (currently only `mcp_status` for #365) is out of
+   scope for #380 but would be useful for v0.36.x.
+
+## References
+
+- `src/untether/runners/claude.py` — auto-approve gate (around the
+  `_AUTO_APPROVE_TYPES` definition; line numbers shift with edits — see the
+  inline comment for the canonical rationale).
+- `src/untether/schemas/claude.py:154-174` — control_request type
+  definitions.
+- `tests/test_claude_control.py::TestAutoApproveSafetyInvariant` — regression
+  locks.
+- `.claude/rules/control-channel.md` — control-channel architecture rules
+  (invariant maintained: PTY lifecycle, session registries, response
+  routing).
+- [Claude Code SDK docs](https://github.com/anthropics/claude-agent-sdk-python)
+  — wire format and subtype semantics.
diff --git a/docs/explanation/architecture.md b/docs/explanation/architecture.md
index 77c608bb..fc55d45f 100644
--- a/docs/explanation/architecture.md
+++ b/docs/explanation/architecture.md
@@ -46,7 +46,7 @@ flowchart TB
     subgraph Triggers["Triggers Layer"]
         trigger_server[triggers/server.py<br/>webhook HTTP server<br/>multipart, rate limit]
         trigger_cron[triggers/cron.py<br/>cron scheduler<br/>timezone, run_once]
-        trigger_manager[triggers/manager.py<br/>TriggerManager<br/>hot-reload]
+        trigger_manager[triggers/manager.py<br/>TriggerManager<br/>hot-reload + pause/resume]
         trigger_dispatch[triggers/dispatcher.py<br/>dispatch to run_job]
         trigger_actions[triggers/actions.py<br/>file_write, http_forward, notify_only]
         trigger_fetch[triggers/fetch.py<br/>cron data-fetch]
@@ -422,6 +422,6 @@ flowchart TD
 | **Bridge** | `telegram/bridge.py`, `runner_bridge.py` | Message handling, execution coordination |
 | **Runner** | `runner.py`, `runners/*.py`, `schemas/*.py` | Agent CLI subprocess, JSONL parsing, event translation |
 | **Transport** | `transport.py`, `presenter.py`, `telegram/client.py` | Telegram API, message rendering |
-| **Triggers** | `triggers/server.py`, `triggers/cron.py`, `triggers/manager.py`, `triggers/dispatcher.py`, `triggers/actions.py`, `triggers/fetch.py`, `triggers/ssrf.py`, `triggers/auth.py`, `triggers/rate_limit.py`, `triggers/describe.py`, `triggers/templating.py` | Webhook server (multipart, rate limit), cron scheduler (timezone, data-fetch, `run_once`), `TriggerManager` for hot-reload, non-agent actions (`file_write`/`http_forward`/`notify_only`), SSRF protection, HMAC/bearer auth, human-friendly cron description |
+| **Triggers** | `triggers/server.py`, `triggers/cron.py`, `triggers/manager.py`, `triggers/dispatcher.py`, `triggers/actions.py`, `triggers/fetch.py`, `triggers/ssrf.py`, `triggers/auth.py`, `triggers/rate_limit.py`, `triggers/describe.py`, `triggers/history.py`, `triggers/templating.py` | Webhook server (multipart, rate limit, `503 triggers paused`), cron scheduler (timezone, data-fetch, `run_once`), `TriggerManager` for hot-reload + master pause/resume toggle, fire-history persistence for `/stats` triggered/manual breakdown, non-agent actions (`file_write`/`http_forward`/`notify_only`), SSRF protection, HMAC/bearer auth, human-friendly cron description |
 | **Domain** | `model.py`, `progress.py`, `events.py` | Event types, action tracking |
 | **Utils** | `worktrees.py`, `utils/*.py`, `markdown.py` | Git worktrees, formatting, paths |
diff --git a/docs/explanation/module-map.md b/docs/explanation/module-map.md
index f010c15b..e1abbe70 100644
--- a/docs/explanation/module-map.md
+++ b/docs/explanation/module-map.md
@@ -19,6 +19,8 @@ This page is a high-level map of Untether’s internal modules: what they do and
 | `transport_runtime.py` | Facade used by transports and commands to resolve messages and runners without importing internal router/project types. |
 | `cost_tracker.py` | Per-run and daily cost tracking with budget alerts and auto-cancel. |
 | `shutdown.py` | Graceful shutdown state and drain logic. |
+| `telegram/at_scheduler.py` | One-shot delayed runs from `/at <duration>`; in-memory state, drained on shutdown. |
+| `telegram/loop_scheduler.py` | Loop mode firing for Claude's `/loop` and `ScheduleWakeup`; persists `active_loops.json` so loops survive restart. Mirrors `at_scheduler` API. |
 
 ## Domain model and events
 
@@ -67,6 +69,17 @@ This page is a high-level map of Untether’s internal modules: what they do and
 | `runners/*` | Engine runner implementations (Claude Code, Codex, OpenCode, Pi, Gemini CLI, Amp). |
 | `schemas/*` | msgspec schemas / decoders for engine JSONL streams. |
 
+## Triggers
+
+| Module | Responsibility |
+|--------|----------------|
+| `triggers/manager.py` | Mutable holder for crons + webhooks; hot-reload on TOML change; master `pause()` / `resume()` / `is_paused` toggle. |
+| `triggers/server.py` | Webhook HTTP server (aiohttp); returns `503 triggers paused` while master pause is active; `/health` reflects paused state. |
+| `triggers/dispatcher.py` | Routes webhook/cron fires to `run_job()` or non-agent action handlers. |
+| `triggers/cron.py` | Cron expression parser, timezone-aware scheduler loop. |
+| `triggers/history.py` | Persistent JSON history of cron/webhook fire times for `/stats` triggered/manual breakdown. |
+| `triggers/describe.py` | Human-friendly cron rendering for `/ping`, `/config → 📡 Triggers`. |
+
 ## Configuration and persistence
 
 | Module | Responsibility |
diff --git a/docs/explanation/routing-and-sessions.md b/docs/explanation/routing-and-sessions.md
index c23ec415..40d16b1b 100644
--- a/docs/explanation/routing-and-sessions.md
+++ b/docs/explanation/routing-and-sessions.md
@@ -28,11 +28,11 @@ Untether supports four ways to continue a thread:
 
 Reply-to-continue works even if topics or chat sessions are enabled.
 
-## Trigger mode (pre-routing filter)
+## Listen mode (pre-routing filter)
 
-Before routing, Untether checks the chat's **trigger mode**. In `mentions` mode, messages that don't @mention the bot, reply to the bot, or start with a known slash command are silently dropped — they never reach the router. In the default `all` mode, every message passes through.
+Before routing, Untether checks the chat's **listen mode** (renamed from "trigger mode" in v0.35.3 — [#297](https://github.com/littlebearapps/untether/issues/297)). In `mentions` mode, messages that don't @mention the bot, reply to the bot, or start with a known slash command are silently dropped — they never reach the router. In the default `all` mode, every message passes through.
 
-Trigger mode is configured per chat via `/trigger` or `/config`, with optional per-topic overrides in forum groups. See [Group chat](../how-to/group-chat.md#set-trigger-mode-for-groups) for details.
+Listen mode is configured per chat via `/listen` (or the deprecated `/trigger` alias) or `/config`, with optional per-topic overrides in forum groups. See [Group chat](../how-to/group-chat.md#set-trigger-mode-for-groups) for details.
 
 ## Routing (how Untether picks a runner)
 
diff --git a/docs/faq/faq.md b/docs/faq/faq.md
new file mode 100644
index 00000000..9db920ad
--- /dev/null
+++ b/docs/faq/faq.md
@@ -0,0 +1,174 @@
+---
+title: "Untether — Frequently Asked Questions"
+description: "Common questions about Untether: installation, supported engines, costs, privacy, troubleshooting, and design choices."
+---
+
+# Frequently Asked Questions
+
+> Quick answers to the questions users ask most often. Also surfaced at
+> <https://littlebearapps.com/help/untether/faq/>.
+
+## What is Untether?
+
+Untether is a Telegram bridge for AI coding agents. It runs on your computer (or a server you control) and forwards messages between Telegram and the agent CLI of your choice — Claude Code, Codex, OpenCode, Pi, Gemini CLI, or Amp.
+
+Your machine still does all the work. Untether is the wire between your phone and the agent, with progress streaming, interactive approval buttons, voice transcription, cost tracking, scheduled runs, and inline settings layered on top. The intent is simple: keep using the same agent you already use, but stop being chained to a terminal window when you want to walk the dog or watch the footy.
+
+## How do I install Untether?
+
+Untether is published to PyPI. With [`uv`](https://docs.astral.sh/uv/) installed:
+
+```sh
+uv tool install untether
+untether
+```
+
+Or with `pipx`:
+
+```sh
+pipx install untether
+untether
+```
+
+The first run launches a setup wizard that creates a Telegram bot via [BotFather](https://t.me/BotFather), picks one of three workflow modes (assistant, workspace, or handoff), and writes `~/.untether/untether.toml`. After the wizard finishes, send a message to your bot in Telegram and the agent runs on your machine.
+
+Already have a bot token? Skip the BotFather step with `untether --bot-token YOUR_TOKEN`. Full walkthrough: [Install and onboard](https://untether.littlebearapps.com/tutorials/install/).
+
+## Which AI coding agents does Untether support?
+
+Untether supports six agent CLIs out of the box:
+
+- **[Claude Code](https://docs.anthropic.com/en/docs/claude-code)** — complex refactors, architecture, long context. Most interactive features (plan mode, ask mode, diff preview, progressive cooldown) are Claude-specific.
+- **[Codex](https://github.com/openai/codex)** — fast edits, shell commands, OpenAI subscription via ChatGPT login.
+- **[OpenCode](https://github.com/opencode-ai/opencode)** — 75+ providers via Models.dev, local model support.
+- **[Pi](https://github.com/mariozechner/pi-coding-agent)** — multi-provider auth, conversational style.
+- **[Gemini CLI](https://github.com/google-gemini/gemini-cli)** — Google Gemini models with configurable approval modes.
+- **[Amp](https://ampcode.com)** — Sourcegraph's coding agent with mode selection.
+
+You can switch between engines per-message by prefixing with `/<engine>` (e.g. `/claude`, `/codex`). Each chat or topic can also have its own default engine. The full per-engine feature matrix is in the [README](https://github.com/littlebearapps/untether#-supported-engines).
+
+## Do I need an API key to use Untether?
+
+In most cases, no. Untether uses whatever authentication your agent CLI already has — your existing Claude Pro/Max subscription via OAuth, your ChatGPT Plus/Pro/Business plan via the Codex device-auth flow, your Gemini account, your Amp Sourcegraph login. If `claude auth status` works on your machine, Untether will use the same authentication.
+
+API keys (`ANTHROPIC_API_KEY`, `OPENAI_API_KEY`, etc.) are only needed if you specifically want API billing instead of a subscription, or for engines that don't offer subscription auth (e.g. some OpenCode providers). Untether itself doesn't make any API calls — it just spawns the agent CLI as a subprocess.
+
+The one exception is voice transcription: Untether ships with optional Whisper-via-Groq support. That's a separate API key (`voice_transcription_api_key`) which is masked in logs as `SecretStr` and only sent to your configured transcription endpoint.
+
+## Where does my code and data go?
+
+Untether runs entirely on your machine (or your server). Your repo, your environment, your authenticated agent — Untether is just a transport.
+
+- **Telegram** sees the messages you exchange with your bot — that's the user-content channel by design. Messages are encrypted in transit but Telegram does have access to them on its servers, so treat the bot like any other chat: don't paste production secrets into prompts.
+- **Your agent CLI** sees whatever you send in the message plus your project's filesystem (subject to whatever permission controls the engine has — Claude's `--permission-mode`, Codex's `--ask-for-approval`, etc.).
+- **The agent's vendor** (Anthropic / OpenAI / Google / Sourcegraph / etc.) sees whatever the agent CLI sends to its API — same as if you ran the CLI directly in a terminal.
+- **Untether itself** doesn't phone home, doesn't send analytics, doesn't have a remote service. Crash logs stay on your machine. The bot token, allowlisted user IDs, and any optional voice-transcription API key live in your local `untether.toml` and are masked in operational logs.
+
+If you want stricter sandboxing, run Untether inside a container or on a VM. The whole bridge is one Python process and a few state files in `~/.untether/`.
+
+## How do I approve tool calls from my phone?
+
+When Claude Code wants to run a tool that needs approval — write a file, run a shell command in plan mode, etc. — Untether posts the request to your Telegram chat with inline buttons: ✅ Approve / ❌ Deny / 📋 Pause & Outline Plan. Tap a button and the agent continues immediately.
+
+If you click "Pause & Outline Plan", Claude writes a plain-language summary of what it's about to do, and you get a second round of buttons: ✅ Approve Plan / ❌ Deny / 💬 Let's discuss. Approving here also auto-approves the next plan-exit so you don't get prompted twice for the same plan.
+
+Per-chat plan mode (`/planmode on/auto/off`) controls when the buttons appear:
+
+- **on** — every plan transition prompts for approval.
+- **auto** — plan transitions auto-approve, but tool approvals still appear.
+- **off** — no plan phase; tools auto-execute (subject to engine policy).
+
+For non-Claude engines, approval is enforced per-engine pre-run (Codex `--ask-for-approval`, Gemini `--approval-mode`) rather than via mid-run buttons. Full guide: [Interactive approval](https://untether.littlebearapps.com/how-to/interactive-approval/).
+
+## What happens if my agent crashes or my phone loses signal mid-run?
+
+Untether is built around the assumption that your phone is unreliable but your computer isn't. Two things matter here:
+
+1. **Your agent keeps running.** It's a subprocess on your machine. It doesn't care whether your phone is connected, whether Telegram is open, or whether you've gone to sleep. Progress messages buffer locally; reconnection rendering is automatic.
+2. **Untether catches the common failure modes.** If a Claude Code session exits prematurely after a tool result without processing it (a known upstream bug), Untether auto-resumes it. If the bot is restarted while a run is in progress, ephemeral approval messages are cleaned up and orphaned progress messages get a `⚠️ interrupted by restart` marker. Stalls that look "alive but silent" trigger progressive warnings, and the watchdog auto-cancels truly dead processes.
+
+Everything important — Telegram update offsets, active progress message references, trigger fire history — is persisted to disk so a restart picks up where you left off without dropping or duplicating messages.
+
+## How do I keep agents from spending too much money?
+
+Untether ships per-run and per-day cost budgets. In `untether.toml`:
+
+```toml
+[cost_budget]
+enabled = true
+max_cost_per_run = 2.00      # USD; warn or auto-cancel if a single run exceeds this
+max_cost_per_day = 10.00     # USD; ditto across a calendar day
+warn_at_pct = 80             # warn when this % of budget is consumed
+auto_cancel_on_exceed = true # cancel the run when the threshold is hit
+```
+
+`/usage` shows the current run's cost; `/usage debug` shows OAuth token expiry, schema-mismatch counters, and cache freshness — useful when the subscription footer goes silent. `/stats` reports per-engine totals across today, this week, and all time.
+
+Cost tracking is most accurate for Claude (full USD reporting via API metadata) and OpenCode. Codex, Pi, Gemini, and Amp report tokens-only. Subscription users (Claude Pro/Max, ChatGPT, Gemini, Amp) see a `5h: N% / 7d: N%` indicator instead of dollars. See the [cost-budgets guide](https://untether.littlebearapps.com/how-to/cost-budgets/) for tuning.
+
+## Does /loop work via Untether?
+
+By default, no — Claude Code's `/loop` and `ScheduleWakeup` are session-scoped, and the Untether subprocess exits when each turn finishes. Schedules registered by Claude don't fire afterwards.
+
+To enable end-to-end /loop support, turn on **Loop mode** in `/config → 🔁 Loop mode`. When on, Untether observes Claude's schedule registrations and re-fires each iteration when due, spawning a fresh `claude --resume` subprocess per fire.
+
+Be aware: autonomous loops consume API credits or your subscription quota. Set a budget in `/config → 💰 Cost & usage` *before* turning Loop mode on — the same daily cost cap applies to loop fires automatically. See the [Schedule tasks how-to](https://untether.littlebearapps.com/how-to/schedule-tasks/#loop-mode) for details.
+
+## Can I send voice notes instead of typing?
+
+Yes — record a voice message in Telegram and Untether transcribes it via a Whisper-compatible endpoint, then runs the transcribed text as a normal prompt. Configure in `untether.toml`:
+
+```toml
+[transports.telegram]
+voice_transcription = true
+voice_transcription_model = "whisper-large-v3-turbo"
+voice_transcription_base_url = "https://api.groq.com/openai/v1"
+voice_transcription_api_key = "gsk_..."   # SecretStr — masked in logs
+```
+
+Groq's Whisper Large v3 Turbo is fast and cheap; any OpenAI-compatible Whisper endpoint works (including a self-hosted one). The API key is `SecretStr`-masked in `repr()` / `str()` / structlog so it never lands in journal or crash output. Full setup: [Voice notes](https://untether.littlebearapps.com/how-to/voice-notes/).
+
+## How do I update Untether?
+
+If you installed with `uv`:
+
+```sh
+uv tool upgrade untether
+```
+
+If you installed with `pipx`:
+
+```sh
+pipx upgrade untether
+```
+
+Then restart the running bot to pick up the new wheel. If you're running interactively, send `/restart` from Telegram — it drains active runs first, then exits, and your launcher restarts the process. If you're running under systemd:
+
+```sh
+systemctl --user restart untether
+```
+
+Untether follows semver: patch versions (e.g. `0.35.2 → 0.35.3`) are bug fixes, minor versions (`0.34.x → 0.35.0`) add features, major versions break config or runner protocol. Pre-release `rcN` wheels publish to TestPyPI for staging dogfooding. The [CHANGELOG](https://github.com/littlebearapps/untether/blob/master/CHANGELOG.md) lists every change with linked GitHub issues.
+
+## How do I uninstall Untether?
+
+```sh
+uv tool uninstall untether
+# or
+pipx uninstall untether
+
+rm -rf ~/.untether/
+```
+
+That removes the CLI, all state files (chat preferences, session resumes, trigger history), and your `untether.toml`. If you set up a systemd user unit, also `systemctl --user disable --now untether` and remove the unit file.
+
+The Telegram bot itself lives on Telegram's side — to delete it entirely, talk to [@BotFather](https://t.me/BotFather), pick `/deletebot`, and select your bot. That step is optional; an inactive bot causes no harm beyond squatting the username. Full uninstall walkthrough: [Uninstall Untether](https://untether.littlebearapps.com/how-to/uninstall/).
+
+## Where can I get help or report a bug?
+
+- **Documentation** — [`docs/`](https://github.com/littlebearapps/untether/tree/master/docs) covers tutorials, how-to guides, engine references, and architecture.
+- **Help centre** — <https://untether.littlebearapps.com>
+- **Bug reports and feature requests** — [GitHub Issues](https://github.com/littlebearapps/untether/issues) with the `bug` or `enhancement` label.
+- **Security issues** — see [SECURITY.md](https://github.com/littlebearapps/untether/blob/master/SECURITY.md) for the responsible-disclosure path.
+
+When filing an issue, include your Untether version (`untether --version`), the engine + version that reproduced the bug, and a relevant excerpt from `journalctl --user -u untether` (or the equivalent log path for your runtime). Sensitive paths and secrets are scrubbed from logs by default but spot-check before pasting.
diff --git a/docs/how-to/cost-budgets.md b/docs/how-to/cost-budgets.md
index bd5cf046..fbe74a34 100644
--- a/docs/how-to/cost-budgets.md
+++ b/docs/how-to/cost-budgets.md
@@ -38,6 +38,9 @@ You can toggle budgets on or off per chat without editing the config file. Open
 
 These override the global `[cost_budget]` settings for the specific chat. Clear the override to revert to the global setting. See [Inline settings](inline-settings.md) for the full `/config` menu reference.
 
+!!! warning "Loop mode and budgets"
+    If you turn on Loop mode in `/config → 🔁 Loop mode`, autonomous loop fires count toward the same daily and per-run budget caps as manual runs. There is no separate per-loop budget — the existing `max_cost_per_day` cap auto-cancels any loop iteration that would exceed it. **Set a budget before turning on Loop mode** to bound your exposure. See [Schedule tasks → Loop mode](schedule-tasks.md#loop-mode) for the full picture. ([#289](https://github.com/littlebearapps/untether/issues/289))
+
 ## How it works
 
 After each run completes, Untether checks the reported cost against your budgets:
diff --git a/docs/how-to/group-chat.md b/docs/how-to/group-chat.md
index 1a952f9b..02fb29fc 100644
--- a/docs/how-to/group-chat.md
+++ b/docs/how-to/group-chat.md
@@ -11,7 +11,7 @@ Add your Untether bot to a Telegram group like any other member. If you plan to
 
 ## Restrict access with allowed_user_ids
 
-By default, anyone in the group can interact with the bot. To restrict access to specific users, set `allowed_user_ids`:
+`allowed_user_ids` is required as of v0.35.3 ([#377](https://github.com/littlebearapps/untether/issues/377)) — see [security.md](security.md#restrict-access). Set it to a non-empty list of Telegram user IDs:
 
 === "untether config"
 
@@ -26,7 +26,7 @@ By default, anyone in the group can interact with the bot. To restrict access to
     allowed_user_ids = [12345, 67890]
     ```
 
-When `allowed_user_ids` is non-empty, only listed Telegram user IDs can start runs and interact with the bot. Messages from other users are silently ignored.
+Only listed Telegram user IDs can start runs and interact with the bot. Messages from other users are silently ignored.
 
 To find your Telegram user ID, run:
 
@@ -44,22 +44,25 @@ In group chats, each user gets their own independent session. User A's conversat
 
 In group chats, approval buttons (Approve, Deny, Pause & Outline Plan) are validated against `allowed_user_ids`. If a group member who is not in the allowed list taps another user's approval buttons, the press is rejected — they cannot approve or deny tool calls on someone else's behalf.
 
-This also applies to cancel buttons. When `allowed_user_ids` is empty (the default), all group members can interact with any buttons.
+This also applies to cancel buttons. (When `allow_any_user = true` is set as the dev/demo escape hatch, all group members can interact with any buttons since there's no allowlist to validate against.)
 
-## Set trigger mode for groups
+## Set listen mode for groups
 
 By default, the bot responds to every message (`all` mode). In busy groups, switch to `mentions` mode so the bot only responds when @mentioned:
 
 ```
-/trigger mentions
+/listen mentions
 ```
 
 | Command | Behaviour |
 |---------|-----------|
-| `/trigger` | Show the current trigger mode |
-| `/trigger all` | Respond to every message |
-| `/trigger mentions` | Only respond to @bot_name mentions |
-| `/trigger clear` | Reset to the default (`all`) |
+| `/listen` | Show the current listen mode |
+| `/listen all` | Respond to every message |
+| `/listen mentions` | Only respond to @bot_name mentions |
+| `/listen clear` | Reset to the default (`all`) |
+
+!!! note "Renamed from `/trigger` in v0.35.3"
+    The old `/trigger` command was renamed to `/listen` to disambiguate from the webhook/cron triggers system. `/trigger` continues to work as a deprecated alias for one release cycle and shows a one-line deprecation notice — it will be removed in a future version.
 
 !!! tip "What triggers a response in mentions mode"
     In `mentions` mode, the bot responds when any of these conditions are met:
@@ -71,7 +74,7 @@ By default, the bot responds to every message (`all` mode). In busy groups, swit
     All other messages are silently ignored.
 
 !!! note "Per-topic overrides"
-    In forum groups, you can set trigger mode per topic. A topic override takes priority over the chat-level default. For example, set `mentions` on general chat but leave coding topics on `all`. See [Topics](topics.md) for details.
+    In forum groups, you can set listen mode per topic. A topic override takes priority over the chat-level default. For example, set `mentions` on general chat but leave coding topics on `all`. See [Topics](topics.md) for details.
 
 ## Admin-only commands
 
@@ -80,7 +83,7 @@ In group chats, certain commands require admin or creator status:
 - `/model` — change the model
 - `/reasoning` — change reasoning level
 - `/agent` — change the default engine
-- `/trigger` — change trigger mode
+- `/listen` — change listen mode (also accepts the deprecated `/trigger`)
 
 In private chats, these commands are always available without restriction.
 
diff --git a/docs/how-to/inline-settings.md b/docs/how-to/inline-settings.md
index 30268759..855d4206 100644
--- a/docs/how-to/inline-settings.md
+++ b/docs/how-to/inline-settings.md
@@ -25,12 +25,12 @@ Cost & usage: cost on, sub off
 Resume line: on
 Engine: claude (global)
 Model: default
-Trigger: all
+Listen: all
 
 [📋 Plan mode]     [❓ Ask mode]
 [📝 Diff preview]  [🔍 Verbose]
 [💰 Cost & usage]  [↩️ Resume line]
-[📡 Trigger]       [⚙️ Engine & model]
+[📡 Listen]        [⚙️ Engine & model]
 [🧠 Reasoning]     [ℹ️ About]
 
 📖 Help guides · 🐛 Report a bug
@@ -98,12 +98,42 @@ When you switch engines via the Engine & model page, the home page automatically
 | Effort / Reasoning | Claude: low, medium, high, xhigh, max; Codex: minimal, low, medium, high, xhigh | Yes (chat prefs) |
 | Cost & usage | API cost, subscription usage, budget, auto-cancel | Yes (chat prefs) |
 | Resume line | off, on | Yes (chat prefs) |
-| Trigger | all, mentions | Yes (chat prefs) |
+| Listen | all, mentions | Yes (chat prefs) |
 | Budget enabled | off, on | Yes (chat prefs) |
 | Budget auto-cancel | off, on | Yes (chat prefs) |
 
 Approval policy appears instead of Plan mode when the engine is Codex CLI. Approval mode appears instead of Plan mode when the engine is Gemini CLI.
 
+### Triggers page {#triggers-page}
+
+When `[triggers]` is enabled and at least one cron or webhook is configured, the home page gains a one-button toggle row at the bottom and a dedicated `📡 Triggers` button that opens the Triggers page (`config:tg`) ([#271](https://github.com/littlebearapps/untether/issues/271) Tier 2 + [#294](https://github.com/littlebearapps/untether/issues/294)).
+
+The Triggers page shows:
+
+* **State and counts** — `running` / `paused`, plus per-chat cron and webhook totals.
+* **Master pause/resume toggle** — tap **Pause** to suspend all cron firing and webhook dispatch globally without editing config; tap **Resume** to clear it. While paused, webhooks return `503 triggers paused` (with `Retry-After: 60`), `/health` reports `paused: true`, and `/ping` shows `⏸ triggers paused: … (suspended)`. Pause is in-memory only — restart auto-resumes (the safe default).
+* **Per-chat cron list** — each line shows the cron `id`, human-readable schedule via `describe_cron(schedule, timezone)`, project, engine, and last-fired relative time.
+* **Per-chat webhook list** — each line shows the webhook `id`, path, auth scheme, project, engine, and last-fired.
+
+Lists are scoped to the current chat (`crons_for_chat()` / `webhooks_for_chat()` with the bridge `default_chat_id` fallback), capped at 10 entries with a `…and N more (see untether.toml)` overflow marker. The pause/resume controls remain visible even when the chat has no triggers configured.
+
+See [Schedule tasks](schedule-tasks.md#pausing-all-triggers) for the pause flow end-to-end.
+
+### Loop mode page {#loop-mode}
+
+When the active engine is Claude Code, the home page gains a `🔁 Loop mode` button that opens the Loop sub-page ([#289](https://github.com/littlebearapps/untether/issues/289)). Loop mode is **off by default** — turning it on enables Untether's observation of Claude's session-scoped scheduling tools (`CronCreate`, `ScheduleWakeup`) so iterations keep firing after the subprocess exits.
+
+The page shows:
+
+* **State** — `Loop mode: on` / `off` for the current chat (per-chat override over the global `[loop] enabled` default).
+* **Cost + quota warning** — explicit reminder before turning ON: every loop fire counts against `[cost_budget]`, and the runaway caps in `[loop]` (`max_iterations`, `max_total_duration_hours`, `expiry_days`) are the safety net.
+* **💰 Set a budget** — deep-link to the `Cost & Usage` page (`config:cu`) for one-tap budget setup.
+* **Toggle row** — `[On] [Off] [Clear]` with ✓ on the active option.
+
+`/cancel` and `/new` both drop pending loop iterations for the current session and write a do-not-resume sentinel so a subsequent `loop_scheduler` resume can't replay them. `/continue` is unaffected (it doesn't trigger loop replay).
+
+Loop mode is **Claude-only** (`LOOP_SUPPORTED_ENGINES = frozenset({"claude"})`); the button is hidden for other engines. See [Schedule tasks → Loop mode](schedule-tasks.md#loop-mode) for the full architecture and cost guidance.
+
 ### Cost & Usage page
 
 The Cost & Usage sub-page merges cost display and budget controls into a unified page with toggle rows:
@@ -131,4 +161,4 @@ All button interactions use early callback answering for instant feedback.
 - [Cost budgets](cost-budgets.md) — budget configuration and alerts
 - [Verbose progress](verbose-progress.md) — verbose mode details and global config
 - [Switch engines](switch-engines.md) — engine selection
-- [Group chat](group-chat.md) — trigger mode in groups
+- [Group chat](group-chat.md) — listen mode in groups
diff --git a/docs/how-to/operations.md b/docs/how-to/operations.md
index fada08f7..4af21b8e 100644
--- a/docs/how-to/operations.md
+++ b/docs/how-to/operations.md
@@ -37,7 +37,9 @@ Returns `{"status": "ok", "webhooks": N}` where N is the number of configured we
     💰 today: $1.42
     ⏱ uptime: 3d 14h 22m
 
-Each section degrades gracefully when its source is unavailable (non-Linux, no `trigger_manager`, no cost tracker). `/health` is project-aware — `children` reflects the current Untether process tree (Claude Code subprocesses, MCP servers, workerd grandchildren under #275-style cleanup). When triggers are disabled in config, the line reads `triggers: disabled`.
+Each section degrades gracefully when its source is unavailable (non-Linux, no `trigger_manager`, no cost tracker). `/health` is project-aware — `children` reflects the current Untether process tree (Claude Code subprocesses, MCP servers, workerd grandchildren under #275-style cleanup). When triggers are disabled in config, the line reads `triggers: disabled`. When the master pause toggle ([#294](https://github.com/littlebearapps/untether/issues/294)) is engaged, `/health` reports `{"status":"paused","paused":true}` so external monitors can distinguish "paused but up" from healthy.
+
+For Claude subscription diagnostics, use `/usage debug` ([#410](https://github.com/littlebearapps/untether/issues/410)) — it appends a `🔧 debug` block to the standard `/usage` output showing last-fetch wall time and freshness, last-error class+message, OAuth token expiry, and the cumulative `claude_usage.schema_mismatch` counter. See [Subscription usage](subscription-usage.md#debug-page-usage-debug).
 
 ## RAM guard (#350)
 
@@ -183,7 +185,12 @@ When enabled, Untether watches the config file for changes and reloads most sett
 **Hot-reloadable** (applied immediately):
 
 - Trigger system: `triggers.enabled`, crons, webhooks, auth, rate limits, timezones
-- Telegram bridge: `voice_transcription`, `[files]`, `allowed_user_ids`, `show_resume_line`, timing
+- Telegram bridge: `voice_transcription`, `[files]`, `allowed_user_ids`, `allow_any_user`, `show_resume_line`, timing
+- `[security]` keys: `env_extra_allow`, `env_extra_prefix_allow` (re-read on next runner spawn)
+- `[progress]` keys: `max_actions`, `verbosity`, `min_render_interval`, `group_chat_rps`, `heartbeat_interval` ([#269](https://github.com/littlebearapps/untether/issues/269), [#481](https://github.com/littlebearapps/untether/issues/481))
+- `[watchdog]` keys: `tool_timeout`, `mcp_tool_timeout`, `claude_stream_idle_timeout_ms`, `post_result_idle_timeout`, `post_result_idle_enabled`, `bash_grace_seconds` (re-read per run)
+- Trigger pause/resume: in-memory only, toggled via `/config → 📡 Triggers` ([#294](https://github.com/littlebearapps/untether/issues/294)) — restart auto-resumes
+- `[footer]` and `[cost]` settings (re-read per call)
 - Engine defaults, budget, cost/usage display flags
 
 **Restart-only** (require `/restart` or `systemctl restart`):
diff --git a/docs/how-to/schedule-tasks.md b/docs/how-to/schedule-tasks.md
index 280f21d1..72b93e83 100644
--- a/docs/how-to/schedule-tasks.md
+++ b/docs/how-to/schedule-tasks.md
@@ -1,6 +1,9 @@
 # Schedule tasks
 
-There are several ways to run tasks on a schedule: the `/at` command for quick one-shot delays, Telegram's built-in message scheduling, and Untether's trigger system (webhooks and cron).
+There are several ways to run tasks on a schedule: the `/at` command for quick one-shot delays, Telegram's built-in message scheduling, Untether's trigger system (webhooks and cron), and Loop mode for Claude Code's `/loop` and `ScheduleWakeup`.
+
+!!! note "Loop mode is opt-in"
+    By default, Untether does **not** fire Claude Code's session-scoped schedules after a turn ends — the `claude --print` subprocess exits and the cron task dies with it (verified empirically against `claude` v2.1.129/2.1.132 — upstream docs claiming `--resume` restores tasks are incorrect in `--print` mode). To enable autonomous loop firing via Telegram, turn on **Loop mode** in `/config → 🔁 Loop mode`. See [Loop mode](#loop-mode) below.
 
 ## One-shot delays with /at
 
@@ -28,6 +31,44 @@ When the delay expires, the prompt runs as a normal agent session. Use `/cancel`
 !!! note "Engine and project frozen at schedule time"
     When you run `/at`, Untether snapshots the chat's current project mapping and engine at that moment. That snapshot is what fires when the delay expires — changing `/agent`, `/ctx`, or `/planmode` afterwards does **not** affect already-scheduled delays. Cancel with `/cancel` and re-schedule if you change your mind. ([#362](https://github.com/littlebearapps/untether/issues/362))
 
+## Loop mode
+
+Claude Code has a built-in `/loop <interval> <prompt>` command (and a no-interval `/loop <prompt>` dynamic mode driven by `ScheduleWakeup`) for self-pacing autonomous work. Untether's **Loop mode** observes those tool calls at the JSONL layer, captures the user's intent, and re-fires each iteration when due — even after the subprocess exits. ([#289](https://github.com/littlebearapps/untether/issues/289))
+
+**Default OFF** — opt-in per chat via `/config → 🔁 Loop mode`. When OFF, behaviour matches the prior-version baseline: `/loop` registers a schedule during the turn but nothing fires after the subprocess exits.
+
+### How it works
+
+1. You type `/loop 5m check the deploy` in a Claude session.
+2. Claude calls `CronCreate(cron="*/5 * * * *", prompt="check the deploy", recurring=true)`.
+3. Untether observes the `tool_use` event and registers an Untether-side timer.
+4. The subprocess exits cleanly. Upstream's session-scoped cron dies with it.
+5. Each fire interval, Untether spawns `claude --resume <session_id>` with a wrapped re-issue prompt: `Loop iteration N: check the deploy. Do the task now; do not summarize old results unless necessary.`
+6. State persists to `active_loops.json` (sibling of `untether.toml`) — loops survive Untether restarts.
+
+### Runaway-safety caps
+
+The `[loop]` config has caps in case a loop runs longer than expected:
+
+- `max_iterations = 20` — cap on iteration count (NOT a cost cap)
+- `max_total_duration_hours = 4` — wall-clock cap (NOT a cost cap)
+- `expiry_days = 7` — auto-expire 7 days after creation (matches upstream)
+
+These bound loop duration regardless of cost. They are *not* a substitute for setting a budget — see "Cost considerations" below.
+
+### Cost considerations
+
+Autonomous loops consume API credits or your Claude subscription quota. A 24-hour `/loop 1m` can fire up to 1440 times. Cost per fire depends on conversation length:
+
+- Short conversations: ~$0.01–$0.05 per fire (cache-warm).
+- Long conversations: cache may evict between fires, costing $0.10–$0.50 per fire.
+
+**Set a daily budget BEFORE turning on Loop mode** in `/config → 💰 Cost & usage` (or `[cost_budget].max_cost_per_day` in `untether.toml`). The same daily cost cap applies to loop fires automatically — there is no separate per-loop budget. See [Cost budgets](cost-budgets.md) for setup.
+
+### Cancelling a loop
+
+`/cancel` drops all active loops for the current chat and writes a do-not-resume sentinel so the upstream session-scoped cron — if it ever survives — cannot be re-fired by Untether. `/new` does the same (treats `/new` as "wipe this chat's state").
+
 ## Telegram scheduling
 
 Telegram's native message scheduling works with Untether out of the box.
@@ -94,6 +135,30 @@ permission_mode = "auto"
 
 Precedence (Claude): cron `permission_mode` > per-chat `/planmode` > engine config default. Every autonomous run logs `trigger.cron.permission_mode_override`. Valid values: `default`, `plan`, `auto`, `acceptEdits`, `bypassPermissions`. Claude-only for now; other engines silently ignore the field ([#332](https://github.com/littlebearapps/untether/issues/332) tracks full coverage).
 
+## Trigger provenance and history
+
+Trigger-initiated runs are visibly distinct from manual ones — every run footer carries a provenance marker:
+
+* `⏰ cron:<id>` — fired by a cron trigger
+* `⚡ webhook:<id>` — fired by a webhook trigger
+* `⏰ at:<token>` — fired by `/at`
+
+`/stats` reports a per-engine `(N triggered, M manual)` breakdown next to each engine line and on the totals row when at least one count is nonzero ([#271](https://github.com/littlebearapps/untether/issues/271) Tier 3).
+
+`/config → 📡 Triggers` (`config:tg`) lists every cron and webhook configured for the current chat — for crons: `describe_cron(schedule, timezone)`, project, engine, last-fired relative time; for webhooks: path, auth scheme, project, engine, last-fired. Lists are scoped to the current chat, capped at 10 entries with a `…and N more (see untether.toml)` overflow marker. The page also hosts the master pause/resume toggle (see below). See [Inline settings](inline-settings.md#triggers-page) for the navigation walkthrough.
+
+Last-fired times are persisted to `triggers_history.json` (sibling of `untether.toml`) so the values survive a restart. Renaming a trigger ID in TOML leaves a stale entry that operators can manually delete (no auto-prune to avoid losing data on transient TOML errors).
+
+## Pausing all triggers
+
+When you need to silence the bot for maintenance, demos, or a noisy upstream, the master pause toggle suspends all cron firing and webhook dispatch globally without changing your config ([#294](https://github.com/littlebearapps/untether/issues/294)).
+
+* **From `/config`:** open `📡 Triggers` (or use the one-button toggle row on the home page when triggers are configured) and tap **Pause**.
+* **While paused:** the cron scheduler skips its tick (`run_once` crons are not consumed during the pause and fire on the next matching tick after resume); the webhook server returns `503 triggers paused` with `Retry-After: 60` instead of dispatching; `/health` reports `{"status":"paused","paused":true}` for external monitors; `/ping` shows `⏸ triggers paused: … (suspended)`.
+* **Restart auto-resumes** — pause is in-memory only by design; restarting the bot is a safe escape hatch.
+
+Tap **Resume** in the same page to clear the pause.
+
 ## Webhook triggers
 
 Webhooks let external services (GitHub, Slack, PagerDuty) trigger agent runs via HTTP POST.
diff --git a/docs/how-to/security.md b/docs/how-to/security.md
index 440f386f..04cafbaa 100644
--- a/docs/how-to/security.md
+++ b/docs/how-to/security.md
@@ -4,7 +4,7 @@ Untether gives remote access to coding agents on your server, so locking down wh
 
 ## Restrict access
 
-By default, anyone who can message your bot can start agent runs. To restrict access to specific Telegram users, set `allowed_user_ids`:
+`allowed_user_ids` is **required** as of v0.35.3 ([#377](https://github.com/littlebearapps/untether/issues/377)). Set it to a non-empty list of Telegram user IDs:
 
 === "untether config"
 
@@ -19,7 +19,7 @@ By default, anyone who can message your bot can start agent runs. To restrict ac
     allowed_user_ids = [12345, 67890]
     ```
 
-When this list is non-empty, only the listed user IDs can interact with the bot. Messages from everyone else are silently ignored. In group chats, `allowed_user_ids` also governs button press validation — unauthorised users cannot tap Approve/Deny buttons on another user's tool requests. See [Group chat](group-chat.md#button-press-validation) for details.
+Only listed user IDs can interact with the bot. Messages from everyone else are silently ignored. In group chats, `allowed_user_ids` also governs button press validation — unauthorised users cannot tap Approve/Deny buttons on another user's tool requests. See [Group chat](group-chat.md#button-press-validation) for details.
 
 To find your Telegram user ID:
 
@@ -29,8 +29,11 @@ untether chat-id
 
 Send a message in the target chat and Untether prints the chat ID and sender ID.
 
-!!! warning "Empty list means open access"
-    If `allowed_user_ids` is empty (the default), anyone who discovers your bot's username can start runs. Always set this in production.
+!!! danger "Open-bot opt-out (dev/demo only)"
+    If you genuinely need an open bot for a hackathon, demo, or local-only dev, you can opt out with `allow_any_user = true` under `[transports.telegram]`. Untether logs this at INFO every boot (`security.allow_any_user`) so the deviation is visible in `journalctl`. Never enable this on a host reachable from production traffic — anyone who learns the bot username gains command access.
+
+!!! warning "Pre-v0.35.3 deployments"
+    Before v0.35.3 the empty default was a silent insecure default — bots ran with no allowlist filter and a single warning log line. Upgrading to v0.35.3 surfaces this as a hard `ConfigError` at startup. If your bot fails to start with `[transports.telegram] allowed_user_ids is empty`, populate the list (recommended) or set `allow_any_user = true` to keep the prior behaviour.
 
 ## Protect your bot token
 
@@ -51,13 +54,30 @@ export UNTETHER_CONFIG_PATH=/path/to/untether.toml
 ```
 
 !!! tip "Automatic log redaction"
-    Untether automatically redacts bot tokens, OpenAI API keys (`sk-...`), and GitHub tokens (`ghp_`, `ghs_`, `github_pat_`) from all structured log output. Even if a token appears in engine output or error messages, it is replaced with `[REDACTED]` before being written to logs.
+    Untether automatically redacts bot tokens, OpenAI API keys (`sk-...` and `sk-proj-...` since v0.35.3 — [#213](https://github.com/littlebearapps/untether/issues/213)), and GitHub tokens (`ghp_`, `ghs_`, `github_pat_`) from all structured log output. Even if a token appears in engine output or error messages, it is replaced with `[REDACTED]` before being written to logs. The Telegram voice transcription API key is wrapped in `SecretStr` so it never appears in `repr()`/tracebacks/structlog ([#378](https://github.com/littlebearapps/untether/issues/378)). Stderr path sanitisation also covers macOS (`/Users/<user>/`, `/private/var/...`), container roots (`/app/`, `/workspace/`), and other absolute paths beyond `/home/<user>/` (`/var/`, `/tmp/`, `/opt/`, `/srv/`, `/etc/`, `/usr/local/`, `/root/`) since v0.35.3 ([#208](https://github.com/littlebearapps/untether/issues/208)); path:line markers (`:42`) survive sanitisation so stack traces remain useful.
+
+!!! tip "Pi session directory permissions ([#207](https://github.com/littlebearapps/untether/issues/207))"
+    Pi engine session directories are created with explicit `0o700` mode (and any pre-existing dir gets `chmod`'d to `0o700` on first use) so other users on shared hosts can't read Pi session JSONL files. Applies as of v0.35.3 — no operator action needed.
 
 ## Engine subprocess env allowlist
 
 Claude and Pi engine subprocesses do **not** inherit Untether's full environment. Only allowlisted variables (OS essentials, AI/cloud provider keys, Claude/MCP/Node/Python/UV/NPM namespaces, git/ssh auth) pass through — random third-party tokens that happen to live in your shell (`AWS_*`, `STRIPE_*`, `DATABASE_URL`, personal app tokens, etc.) are **not** available to the engine or its MCP servers. This reduces the blast radius of any tool call or MCP that exfiltrates process env.
 
-If a new engine or MCP genuinely needs a variable that isn't allowlisted (symptom: hangs at init, silent `KeyError` in logs), add it to `_EXACT_ALLOW` / `_PREFIX_ALLOW` in `src/untether/utils/env_policy.py`. Other engines (Codex, Gemini, OpenCode, AMP) still inherit the full parent env — extending the allowlist to them is tracked in [#332](https://github.com/littlebearapps/untether/issues/332).
+If a new engine or MCP genuinely needs a variable that isn't allowlisted (symptom: hangs at init, silent `KeyError` in logs), you have two options:
+
+1. **Recommended for most users (v0.35.3+)**: extend the allowlist via TOML config — no fork, no re-install:
+
+    ```toml title="~/.untether/untether.toml"
+    [security]
+    env_extra_allow = ["OP_SERVICE_ACCOUNT_TOKEN", "DOPPLER_TOKEN"]
+    env_extra_prefix_allow = ["VAULT_", "INFISICAL_"]
+    ```
+
+    Names must match `[A-Z_][A-Z0-9_]*`. Untether logs `env_policy.user_extension` once per process at first runner spawn so the addition is visible in `journalctl`. The runtime audit also honours these so user-allowed names aren't false-flagged as leaks. See [config: `[security]`](../reference/config.md#security) ([#409](https://github.com/littlebearapps/untether/issues/409)).
+
+2. **For names that benefit every Untether user**: add to `_EXACT_ALLOW` / `_PREFIX_ALLOW` in `src/untether/utils/env_policy.py` and submit a PR. `BWS_ACCESS_TOKEN` (Bitwarden Secrets Manager) was promoted into the built-in defaults in v0.35.3 by exactly this path.
+
+Other engines (Codex, Gemini, OpenCode, AMP) still inherit the full parent env — extending the allowlist to them is tracked in [#332](https://github.com/littlebearapps/untether/issues/332).
 
 ### Boundary enforcement on Claude exec ([#361](https://github.com/littlebearapps/untether/issues/361))
 
diff --git a/docs/how-to/subscription-usage.md b/docs/how-to/subscription-usage.md
index 1ebb9a2d..461c722e 100644
--- a/docs/how-to/subscription-usage.md
+++ b/docs/how-to/subscription-usage.md
@@ -74,6 +74,30 @@ Or disable API cost to show only subscription usage:
     show_subscription_usage = true
     ```
 
+## Debug page (`/usage debug`)
+
+When the subscription usage footer goes silent, run `/usage debug` to see a one-message diagnostic block ([#410](https://github.com/littlebearapps/untether/issues/410)) without grepping `journalctl`:
+
+!!! untether "Untether"
+    **5h window**: 45% used (resets in 2h 15m)
+    …
+    🔧 **debug**
+    Last fetch: 2026-05-04T11:07:32Z (3m ago, fresh)
+    Last error: —
+    OAuth expiry: 2026-05-15T08:00:00Z (10d 21h)
+    Schema-mismatch count: 0
+
+The block shows:
+
+| Field | What it tells you |
+|---|---|
+| **Last fetch** | UTC timestamp + age + freshness label (`fresh` / `stale-while-error`) for the last successful Anthropic API call. |
+| **Last error** | Class name and truncated message of the most recent failure (or `—` if no errors). |
+| **OAuth expiry** | UTC timestamp + hh/mm-until-expiry for the Claude Code OAuth token. Drops to "expired" if the token has lapsed. |
+| **Schema-mismatch count** | Cumulative count of `claude_usage.schema_mismatch` warnings — increments whenever Anthropic ships a usage-payload shape change. Stays at `0` on a healthy host. |
+
+Use this when subscription usage stops appearing in the footer or returns stale numbers — the four fields point at the most likely root causes (auth lapsed, API shape changed, transient HTTP failure, or simply nothing fresh has been fetched yet).
+
 ## Claude Code credentials
 
 The `/usage` command reads your Claude Code OAuth credentials to fetch live data from the Anthropic API. If you see **"No Claude credentials found"**, run `claude login` in your terminal to authenticate.
diff --git a/docs/how-to/troubleshooting.md b/docs/how-to/troubleshooting.md
index b5652f91..a256cc51 100644
--- a/docs/how-to/troubleshooting.md
+++ b/docs/how-to/troubleshooting.md
@@ -25,6 +25,29 @@ $ untether doctor
 <!-- TODO: capture screenshot -->
 <!-- <img src="../assets/screenshots/doctor-output.jpg" alt="untether doctor output showing check results" width="360" loading="lazy" /> -->
 
+## Bot fails to start: `allowed_user_ids is empty`
+
+**Symptoms:** Untether exits at startup with `ConfigError: [transports.telegram] allowed_user_ids is empty …`.
+
+This is the v0.35.3 ([#377](https://github.com/littlebearapps/untether/issues/377)) startup-block. Before v0.35.3 an empty allowlist was a silent insecure default — any Telegram user who knew the bot username could send commands. Fix by either:
+
+- **Recommended**: populate the allowlist with your Telegram user ID(s):
+
+    ```sh
+    untether config set transports.telegram.allowed_user_ids "[<your_id>]"
+    ```
+
+    Get your ID with `untether chat-id` (sends a message in your chat and prints the IDs).
+
+- **Dev/demo escape hatch**: opt in to an open bot. Logged at INFO every boot so the deviation stays visible:
+
+    ```toml title="~/.untether/untether.toml"
+    [transports.telegram]
+    allow_any_user = true
+    ```
+
+See [security.md](security.md#restrict-access) for the full discussion.
+
 ## Bot not responding
 
 **Symptoms:** You send a message but the bot doesn't reply at all.
@@ -33,8 +56,8 @@ $ untether doctor
     - **Terminal**: Look at the terminal where you ran `untether` — is it still running?
     - **Linux (systemd)**: `systemctl --user status untether`
 2. Verify your bot token: `untether doctor` will flag an invalid token
-3. Check `allowed_user_ids` — if set, only listed users can interact. An empty list means everyone is allowed.
-4. In a group chat, check trigger mode: if set to `mentions`, you must @mention the bot
+3. Check `allowed_user_ids` — only listed users can interact. As of v0.35.3, an empty list is rejected at startup unless `allow_any_user = true` is set ([#377](https://github.com/littlebearapps/untether/issues/377)).
+4. In a group chat, check listen mode (`/listen`): if set to `mentions`, you must @mention the bot
 5. Make sure you're messaging the correct bot (not a different one)
 
 ## Engine CLI not found
@@ -167,6 +190,46 @@ This is an upstream Claude Code bug ([#34142](https://github.com/anthropics/clau
 
 **Auto-continue is suppressed for signal deaths** (rc=143/SIGTERM, rc=137/SIGKILL) to prevent death spirals under memory pressure. See the [config reference](../reference/config.md#auto_continue).
 
+## "Stream idle timeout - partial response received" (Claude)
+
+**Symptoms:** Claude Code fails with `API Error: Stream idle timeout - partial response received` mid-run, with a Type-A or Type-B classification appended to the failure message.
+
+The error message is classified inline ([#438](https://github.com/littlebearapps/untether/issues/438)) so you don't have to guess which mitigation applies:
+
+* **Type-A (mid-generation stall)** — `num_turns ≥ 1 && duration_api_ms > 0`. Anthropic SSE went silent partway through a generation. Common on long opus 4.7 1M plan-mode runs. **Mitigation:** raise `[watchdog] claude_stream_idle_timeout_ms` to ride out longer silences.
+  ```toml
+  [watchdog]
+  claude_stream_idle_timeout_ms = 600000   # 10 min (default 300000 / 5 min; max 1800000 / 30 min)
+  ```
+  Shell-set `CLAUDE_STREAM_IDLE_TIMEOUT_MS` still wins.
+* **Type-B (cold-start zero-byte stall)** — `num_turns ≤ 1 && duration_api_ms == 0`. The connection opened and went silent before Anthropic produced any tokens. This is an upstream API outage, **not** a watchdog miscalibration — raising the timeout will not help. Wait it out, retry, or check the [Anthropic status page](https://status.anthropic.com).
+
+Auto-retry for Type-A is deferred to a future release pending upstream Anthropic stabilisation.
+
+## Claude session looks alive 30+ min after the final message
+
+**Symptoms:** Claude has clearly finished the turn (you can see the final answer in Telegram), but the session metadata indicates it's still running. The bidirectional Claude CLI is sitting idle holding stdin open.
+
+The post-result idle watchdog ([#333](https://github.com/littlebearapps/untether/issues/333)) closes the gap: every successful `result` event arms `[watchdog] post_result_idle_timeout` (default 600s / 10 min, range 30s–1h). Once the deadline passes the runner closes stdin and the CLI exits cleanly (rc=0). The footer also shows a `✓ turn complete` marker on every successful turn so you have an immediate visual confirmation that the turn has ended even if the process is still alive briefly.
+
+**To disable the timer entirely** (Claude CLI handles its own exit):
+
+```toml
+[watchdog]
+post_result_idle_enabled = false
+```
+
+**To shorten the timeout** for impatient deployments:
+
+```toml
+[watchdog]
+post_result_idle_timeout = 60   # 1 minute
+```
+
+If a button-click `control_response` is mid-flight when the deadline arrives, the timer re-arms instead of closing — preventing orphaned approvals. Look for `claude.post_result_idle.deferred` and `claude.post_result_idle.closing_stdin` in the logs to confirm the watchdog's behaviour.
+
+When the watchdog actually closes stdin, Untether also sends one (and only one) Telegram closing message: `✓ turn complete · session closed after Nm idle`. While the watchdog is running, stall warnings are suppressed (`progress_edits.stall_post_result_suppressed`) so you don't get noise during the legitimate idle window — genuinely-frozen post-result sessions still warn via the frozen-ring escalation.
+
 ## Messages too long or truncated
 
 **Symptoms:** The bot's response is cut off or split across multiple messages.
@@ -321,9 +384,9 @@ This is not a security concern — `UNTETHER_SESSION` is a simple signal variabl
 
 **Symptoms:** Bot works in private chat but ignores messages in a group.
 
-1. Check **trigger mode**: groups default to `mentions` in many setups. Send `/trigger` to check, or `/trigger all` to respond to everything.
+1. Check **listen mode**: groups default to `mentions` in many setups. Send `/listen` to check, or `/listen all` to respond to everything. (`/trigger` still works as a deprecated alias from v0.35.3 onward.)
 2. Check **bot privacy mode** in BotFather: send `/setprivacy` to @BotFather and select your bot. Set to "Disable" so the bot can see all messages (not just commands and @mentions).
-3. Check `allowed_user_ids` — if set, group members not in the list are ignored.
+3. Check `allowed_user_ids` — group members not in the list are ignored. (As of v0.35.3 the list is required at startup unless `allow_any_user = true` is set — see [security.md](security.md#restrict-access).)
 4. If using topics, make sure the bot has "Manage Topics" permission.
 
 ## macOS and Linux credential differences
@@ -451,6 +514,19 @@ Untether recognises **67 error patterns** across 14 categories:
 
 For the full list of patterns and hints, see the [Error Reference](../reference/errors.md).
 
+## Loop didn't fire / loop fired too many times
+
+Loop mode (`/config → 🔁 Loop mode`) gates Untether's observation of Claude Code's `/loop` and `ScheduleWakeup` tools. ([#289](https://github.com/littlebearapps/untether/issues/289))
+
+| Symptom | Likely cause | Fix |
+|---|---|---|
+| `/loop` registered during the turn but no fires happened afterwards | Loop mode toggle is OFF (the default) | `/config → 🔁 Loop mode → 🔁 On` |
+| Loop stopped after N iterations | Hit `[loop] max_iterations` cap | Raise `max_iterations` in `untether.toml`, or restart the loop with a fresh `/loop` |
+| Loop ended with `daily_budget_exceeded` | Hit `[cost_budget] max_cost_per_day` | Raise the cap in `/config → 💰 Cost & usage`, or wait for the daily reset |
+| Loop fires happened but each was a "fresh user turn" rather than autonomous | This is by design — Untether re-issues the original prompt at each fire (see [Schedule tasks → Loop mode](schedule-tasks.md#loop-mode)) | N/A — expected behaviour |
+| Loop kept firing after `/cancel` | Stale `active_loops.json` | Restart `untether` (or the dev/staging unit) — the do-not-resume sentinel is loaded at startup and blocks future fires for cancelled sessions |
+| Loop didn't survive a restart | `active_loops.json` is missing or corrupt | Check `journalctl --user -u untether-dev -f` for `loop.restore.read_failed` warnings; the file lives next to your `untether.toml` |
+
 ## Related
 
 - [Operations and monitoring](operations.md) — `/ping`, `/restart`, hot-reload
diff --git a/docs/how-to/verbose-progress.md b/docs/how-to/verbose-progress.md
index 492d1c8e..1778d37d 100644
--- a/docs/how-to/verbose-progress.md
+++ b/docs/how-to/verbose-progress.md
@@ -79,6 +79,22 @@ Control how many actions appear in the progress message. Actions beyond this lim
 
 Set to `0` to hide the action list entirely, or increase it to see more history.
 
+!!! tip "Hot-reload"
+    `[progress]` settings (`verbosity`, `max_actions`, `heartbeat_interval`, `min_render_interval`, `group_chat_rps`) hot-reload — editing them in `untether.toml` applies on the next run without restart ([#269](https://github.com/littlebearapps/untether/issues/269)).
+
+## Long-running tool tail (heartbeat)
+
+Long-running tool calls (Bash, BashOutput, ScheduleWakeup, Monitor, KillShell, …) get an automatic elapsed-time tail on the progress message after ~60 s — `▸ Bash · 3m 47s · npm run build` — so a glancing user can answer "is it alive? what's it doing? for how long?" without waiting for the next JSONL event ([#481](https://github.com/littlebearapps/untether/issues/481)). The tail appears regardless of `/verbose` state.
+
+In **verbose** mode the tool's `format_verbose_detail` line additionally renders:
+
+- `BashOutput` — the last line of `result_preview` (so 10-min Cloudflare deploy polls show `→ Deploy Production: in_progress` instead of a static `▸ BashOutput`)
+- `ScheduleWakeup` — countdown + reason: `→ fires in 4m 12s · "build check"`
+- `Monitor` — countdown remaining
+- `KillShell` — target shell id
+
+Tune the heartbeat tick via `[progress] heartbeat_interval` (5–120 s, default 30 s) — every tick walks the open-action set and forces a re-render whenever any action is older than 60 s. Strict "rolling stdout sub-line every 5 s" cannot be achieved without upstream Claude Code changes; the BashOutput-polling path is the proxy and refreshes at each polling cycle (~15 s in practice).
+
 ## Per-chat override
 
 The `/verbose` toggle overrides the global config for the current chat. This override persists until you clear it or restart Untether.
diff --git a/docs/how-to/webhooks-and-cron.md b/docs/how-to/webhooks-and-cron.md
index 5afacb57..21538166 100644
--- a/docs/how-to/webhooks-and-cron.md
+++ b/docs/how-to/webhooks-and-cron.md
@@ -242,7 +242,18 @@ Each webhook and cron can specify where the Telegram notification appears:
     max_body_bytes = 1048576  # 1 MB max payload
     ```
 
-The server includes a health endpoint at `GET /health` for uptime monitoring.
+The server includes a health endpoint at `GET /health` for uptime monitoring. While the master pause toggle is active (see [Pause and resume all triggers](#pause-and-resume-all-triggers)) it returns `{"status": "paused", "paused": true}` so external monitors can distinguish "paused but up" from "down".
+
+## Pause and resume all triggers
+
+Untether ships a master pause toggle ([#294](https://github.com/littlebearapps/untether/issues/294)) that gates **both** crons and webhooks at once — useful when deploying, debugging, or muting overnight without editing config:
+
+* **`/config` home page** shows a one-button toggle row at the bottom whenever triggers are configured.
+* **`/config` → `📡 Triggers`** opens a dedicated page with state, per-chat counts, and a Pause/Resume button. It also lists per-chat crons and webhooks with last-fired times.
+* While paused: cron loop skips ticks, webhooks return `503 triggers paused` with `Retry-After: 60`, `/health` returns `paused: true`, and `/ping` shows `⏸ triggers paused: … (suspended)`.
+* `run_once` crons are not consumed during the pause and fire on the next matching tick after resume.
+
+Pause is **in-memory only** — restart auto-resumes (the safe default). For a durable shutoff, set `[triggers] enabled = false` in `untether.toml` instead.
 
 ## Hot-reload configuration
 
diff --git a/docs/reference/commands-and-directives.md b/docs/reference/commands-and-directives.md
index 54a6ea95..f63a76d0 100644
--- a/docs/reference/commands-and-directives.md
+++ b/docs/reference/commands-and-directives.md
@@ -38,7 +38,7 @@ This line is parsed from replies and takes precedence over new directives. For b
 | `/agent` | Show/set the default engine for the current scope. |
 | `/model` | Show/set the model override for the current scope. |
 | `/reasoning` | Show/set the reasoning override for the current scope. |
-| `/trigger` | Show/set trigger mode (mentions-only vs all). |
+| `/listen` | Show/set listen mode (`all` / `mentions` / `clear`) — controls whether the bot responds to every message in a group chat or only to @-mentions. Renamed from `/trigger` in v0.35.3 ([#297](https://github.com/littlebearapps/untether/issues/297)); `/trigger` continues to work as a deprecated alias for one release cycle. |
 | `/file put <path>` | Upload a document into the repo/worktree (requires file transfer enabled). |
 | `/file get <path>` | Fetch a file or directory back into Telegram. Agents can also send files automatically via `.untether-outbox/` — see [file transfer](../how-to/file-transfer.md#agent-initiated-delivery-outbox). |
 | `/topic <project> @branch` | Create/bind a topic (topics enabled). |
@@ -46,19 +46,19 @@ This line is parsed from replies and takes precedence over new directives. For b
 | `/ctx set <project> @branch` | Update context binding. |
 | `/ctx clear` | Remove context binding. |
 | `/planmode` | Toggle Claude Code plan mode (on/auto/off/show/clear). Claude Code only — non-Claude engines are directed to `/config` → Approval policy. |
-| `/usage` | Show Claude Code subscription usage (5h window, weekly, per-model). Claude Code only. Requires Claude Code OAuth credentials (see [troubleshooting](../how-to/troubleshooting.md#claude-code-credentials)). |
+| `/usage` | Show Claude Code subscription usage (5h window, weekly, per-model). Claude Code only. Requires Claude Code OAuth credentials (see [troubleshooting](../how-to/troubleshooting.md#claude-code-credentials)). `/usage debug` appends a `🔧 debug` block with last-fetch wall time and freshness label, last-error class+message, OAuth token expiry, and the cumulative `claude_usage.schema_mismatch` counter ([#410](https://github.com/littlebearapps/untether/issues/410)). |
 | `/export` | Export last session transcript as Markdown or JSON. |
 | `/browse` | Browse project files with inline keyboard navigation. |
 | `/ping` | Health check — replies with uptime since last (re)start. Shows trigger summary if triggers target the current chat. |
 | `/health` | System + triggers + cost snapshot — RAM/swap, Untether process (PID, RSS, FDs, children), trigger counts, today's API cost, uptime. Compact 6-line HTML message; sections degrade gracefully when sources are unavailable. See [operations](../how-to/operations.md#health-snapshot). |
 | `/restart` | Gracefully drain active runs and restart Untether. |
 | `/verbose` | Toggle verbose progress mode (on/off/clear). Shows tool details in progress messages. |
-| `/config` | Interactive settings menu — plan mode, ask mode, verbose, engine, model, reasoning, trigger toggles with inline buttons. |
-| `/stats` | Per-engine session statistics — runs, actions, and duration for today, this week, and all time. Pass an engine name to filter (e.g. `/stats claude`). |
+| `/config` | Interactive settings menu — plan mode, ask mode, verbose, engine, model, reasoning, listen-mode toggles with inline buttons. The `📡 Triggers` page (`config:tg`) lists per-chat crons (`describe_cron(...)` schedule, project, engine, last-fired) and webhooks (path, auth, project, engine, last-fired), capped at 10 entries with an overflow marker, plus a master pause/resume toggle ([#271](https://github.com/littlebearapps/untether/issues/271), [#294](https://github.com/littlebearapps/untether/issues/294)). |
+| `/stats` | Per-engine session statistics — runs, actions, and duration for today, this week, and all time. Includes `(N triggered, M manual)` per-engine breakdown when at least one count is nonzero ([#271](https://github.com/littlebearapps/untether/issues/271) Tier 3). Pass an engine name to filter (e.g. `/stats claude`). |
 | `/auth` | Headless device re-authentication for Codex — runs `codex login --device-auth` and sends the verification URL + device code. `/auth status` checks CLI availability. Codex-only. |
 | `/new` | Cancel any running task and clear stored sessions for the current scope (topic/chat). |
 | `/continue [prompt]` | Resume the most recent session in the project directory. Picks up CLI-started sessions from Telegram. Optional prompt appended. Not supported for AMP. |
-| `/at <duration> <prompt>` | Schedule a one-shot delayed run. Duration: `Ns` (60-9999s), `Nm`, or `Nh` (up to 24h). The chat's project mapping and engine are captured at schedule time and used at fire time (mirrors cron freeze-at-dispatch behaviour). Pending delays are cancelled via `/cancel` and lost on restart. Per-chat cap of 20 pending delays. |
+| `/at <duration> <prompt>` | Schedule a one-shot delayed run. Duration: `Ns` (60-9999s), `Nm`, or `Nh` (up to 24h). The chat's project mapping and engine are captured at schedule time and used at fire time (mirrors cron freeze-at-dispatch behaviour). Pending delays are cancelled via `/cancel` and lost on restart. Per-chat cap of 20 pending delays. Trigger-source provenance is stamped as `at:<token>` and rendered in the run footer (`⏰ at:<token>`), and the run counts toward `/stats` as triggered ([#271](https://github.com/littlebearapps/untether/issues/271) follow-up). |
 
 Notes:
 
@@ -66,6 +66,8 @@ Notes:
 - In topics, `/ctx` binds the topic context.
 - `/new` cancels running tasks and clears sessions but does **not** clear a bound context.
 - `/continue` uses the engine's native "continue" flag: `--continue` (Claude, OpenCode, Pi), `resume --last` (Codex), or `--resume latest` (Gemini).
+- Long-running tools (Bash, BashOutput, ScheduleWakeup, Monitor, …) surface a heartbeat-driven elapsed-time tail (`▸ Bash · 3m 47s · npm run build`) on the progress message after ~60s, regardless of `/verbose` state ([#481](https://github.com/littlebearapps/untether/issues/481)). Tune via `[progress] heartbeat_interval`.
+- Loop mode (Claude only): there is no `/loop` Telegram command — it's a Claude Code feature. Untether observes Claude's `ScheduleWakeup` and `CronCreate` tool calls and re-fires iterations after the subprocess exits. Off by default; opt in per chat via `/config` → 🔁 **Loop mode**. Cost protection lives in `[cost_budget]`, runaway-safety caps in `[loop]` ([#289](https://github.com/littlebearapps/untether/issues/289)).
 
 ## CLI
 
diff --git a/docs/reference/config.md b/docs/reference/config.md
index edc072d2..d0cb443d 100644
--- a/docs/reference/config.md
+++ b/docs/reference/config.md
@@ -78,7 +78,8 @@ systemctl --user restart untether-dev    # dev
 |-----|------|---------|-------|
 | `bot_token` | string | (required) | 🔄 Telegram bot token from @BotFather. Restart-required. |
 | `chat_id` | int | (required) | 🔄 Default chat id. Restart-required. |
-| `allowed_user_ids` | int[] | `[]` | Allowed sender user ids. Empty disables sender filtering; when set, only these users can interact (including DMs). |
+| `allowed_user_ids` | int[] | (required, non-empty) | Allowed sender user ids. **Required for security as of v0.35.3** ([#377](https://github.com/littlebearapps/untether/issues/377)) — set to a non-empty list of Telegram user IDs (your own user id is the typical minimum). An empty list now triggers a hard `ConfigError` at startup unless you opt in to `allow_any_user = true` (see below). |
+| `allow_any_user` | bool | `false` | **Dev/demo escape hatch** ([#377](https://github.com/littlebearapps/untether/issues/377)). Set to `true` to keep the prior insecure-default behaviour where any Telegram user who knows the bot username can send commands. Logged at INFO on every boot (`security.allow_any_user`) so the deviation is visible in `journalctl`. Use only for hackathons, demos, or local dev. |
 | `message_overflow` | `"trim"`\|`"split"` | `"split"` | 🔄 How to handle long final responses. Restart-required. |
 | `forward_coalesce_s` | float | `1.0` | Quiet window for combining a prompt with immediately-following forwarded messages; set `0` to disable. |
 | `voice_transcription` | bool | `false` | Enable voice note transcription. |
@@ -225,15 +226,20 @@ Controls progress message rendering during agent runs.
     [progress]
     verbosity = "verbose"
     max_actions = 8
+    heartbeat_interval = 30
     ```
 
 | Key | Type | Default | Notes |
 |-----|------|---------|-------|
 | `verbosity` | `"compact"` \| `"verbose"` | `"compact"` | `compact` shows status + title only. `verbose` adds tool detail lines (file paths, commands, patterns). |
 | `max_actions` | int (0–50) | `5` | Maximum action lines shown in the progress message. |
+| `heartbeat_interval` | int (5–120) | `30` | Heartbeat tick that re-renders progress messages so long-running tools surface an elapsed-time tail (e.g. `▸ Bash · 3m 47s · npm run build`) without waiting for the next JSONL event ([#481](https://github.com/littlebearapps/untether/issues/481)). |
 
 Per-chat override: `/verbose on` and `/verbose off` override the config default for the current chat without editing the TOML file. `/verbose clear` removes the override.
 
+!!! tip "Hot-reload"
+    Editing `[progress]` in `untether.toml` applies on the next run without restart ([#269](https://github.com/littlebearapps/untether/issues/269)). The default presenter and per-chat `/verbose` overrides both pick up the new values.
+
 ## `cost_budget`
 
 === "toml"
@@ -276,6 +282,10 @@ Budget alerts always appear regardless of `[footer]` settings.
     notify_catalog_refresh = false
     prespawn_ram_warn_mb = 2000
     prespawn_ram_block_mb = 500
+    claude_stream_idle_timeout_ms = 300_000
+    post_result_idle_enabled = true
+    post_result_idle_timeout = 600.0
+    bash_grace_seconds = 60.0
     ```
 
 | Key | Type | Default | Notes |
@@ -293,9 +303,44 @@ Budget alerts always appear regardless of `[footer]` settings.
 | `notify_catalog_refresh` | bool | `false` | Opt-in experimental ([#365](https://github.com/littlebearapps/untether/issues/365)) — after each `tool_result` batch, send an `mcp_status` control_request on Claude's stdin to nudge the catalog. Documented parent→CLI primitive from Anthropic's `claude-agent-sdk-python` (`get_mcp_status`). Logs `catalog.refresh_sent` INFO on success. Default `false` because the upstream refresh effect on the catalog UI is empirical; enable on staging to measure. Claude runner only. |
 | `prespawn_ram_warn_mb` | int | `2000` | Pre-spawn RAM guard ([#350](https://github.com/littlebearapps/untether/issues/350)) — emit `subprocess.prespawn.ram_warning` when free RAM is below this threshold (MB) at engine spawn. `0` disables the warn tier. |
 | `prespawn_ram_block_mb` | int | `500` | Refuse to spawn the engine subprocess (yields `CompletedEvent(ok=False, error="🛑 Insufficient RAM…")`) when free RAM is below this threshold (MB). `0` disables the block tier; `0` for both fully disables the guard. Must be strictly less than `prespawn_ram_warn_mb` when both are set. |
+| `claude_stream_idle_timeout_ms` | int | `300_000` | Sets `CLAUDE_STREAM_IDLE_TIMEOUT_MS` in the Claude Code subprocess env via `setdefault` ([#438](https://github.com/littlebearapps/untether/issues/438)). Range 30 s – 30 min. Long-form opus 4.7 1M plan-mode generations can legitimately idle the SSE stream past 5 min; deployments hitting upstream Anthropic API stalls (Type A — mid-generation) can raise this to `600_000` or `900_000` to ride out longer silences. Type-B failures (cold-start zero-byte, `num_turns ≤ 1 && duration_api_ms == 0`) are upstream API outages — raising this won't help; the failure error message now classifies both modes inline. Shell-set `CLAUDE_STREAM_IDLE_TIMEOUT_MS` still wins. |
+| `post_result_idle_enabled` | bool | `true` | Claude post-result idle watchdog ([#333](https://github.com/littlebearapps/untether/issues/333)) — closes Claude's stdin cleanly after `post_result_idle_timeout` of silence following a `result` event so multi-turn sessions don't sit alive (and billable) for the full upstream ~36 min idle window. Set `false` to disable (Claude will sit idle until the upstream CLI exits on its own). The clean exit is auto-continue safe — `last_event_type=result` is excluded from the auto-continue gate. |
+| `post_result_idle_timeout` | float | `600.0` | Seconds the watchdog waits after a `result` event before closing stdin (30–3600). The first `result` also emits a `✓ turn complete` footer hint so users know the turn is done; when the watchdog actually fires it sends one Telegram message: `✓ turn complete · session closed after Nm idle`. Re-arms (instead of closing) if a control_request or AskUserQuestion is mid-flight, so a button click in flight is never orphaned. |
+| `bash_grace_seconds` | float | `60.0` | Stall-warning grace window for Bash / BashOutput / KillShell tools ([#481](https://github.com/littlebearapps/untether/issues/481)). Range 5–300. While the most-recent action is one of these and within this window of its start, stall warnings (and the `_STALL_MAX_WARNINGS` auto-cancel arm) are suppressed — long builds and deploys are an expected wait, not a hung session. |
 
 The stall monitor in `ProgressEdits` fires at 5 min (300s) idle, 10 min for local tools, 15 min for MCP tools, and 30 min for pending approvals. When a local tool is running and the child process is CPU-active, the first stall warning fires but repeat warnings are suppressed — they resume if CPU goes idle (indicating a genuinely stuck tool). The liveness watchdog in the subprocess layer fires at `liveness_timeout` with `/proc` diagnostics. When `stall_auto_kill` is enabled, auto-kill requires a triple safety gate: timeout exceeded + zero TCP connections + CPU ticks not increasing between snapshots.
 
+### `[loop]`
+
+Controls Untether's observation of Claude Code's session-scoped scheduling tools (`CronCreate`, `ScheduleWakeup`). Off by default — users opt in per chat via `/config → 🔁 Loop mode`. ([#289](https://github.com/littlebearapps/untether/issues/289))
+
+=== "toml"
+
+    ```toml
+    [loop]
+    enabled = false
+    inline_threshold_seconds = 300
+    redundancy_check_interval = 30
+    max_iterations = 20
+    max_total_duration_hours = 4
+    min_interval_seconds = 60
+    expiry_days = 7
+    ```
+
+| Key | Type | Default | Notes |
+|-----|------|---------|-------|
+| `enabled` | bool | `false` | Global default for Loop mode. Per-chat override available via `/config → 🔁 Loop mode`. |
+| `inline_threshold_seconds` | int | `300` | `ScheduleWakeup` calls with `delaySeconds` ≤ this stay rendered live by the rc8 countdown — no Untether-side timer is registered. Long waits (above the threshold) get an Untether timer that survives subprocess exit. |
+| `redundancy_check_interval` | int | `30` | Seconds the fire path waits before retrying when the originating subprocess is still alive (race-avoidance gate). |
+| `max_iterations` | int | `20` | Runaway-safety cap on iteration count (NOT a cost cap). |
+| `max_total_duration_hours` | int | `4` | Runaway-safety cap on wall-clock duration (NOT a cost cap). |
+| `min_interval_seconds` | int | `60` | Minimum interval between fires (matches upstream cron floor). |
+| `expiry_days` | int | `7` | Auto-expire loops 7 days after creation (matches upstream's session-task expiry). |
+
+**Cost limits are NOT in `[loop]`** — they live in `[cost_budget]` and apply to loop fires automatically. See [Cost budgets](../how-to/cost-budgets.md) for setup.
+
+State is persisted to `active_loops.json` (sibling of your `untether.toml`) so loops survive restarts. The do-not-resume sentinel for `/cancel`-cancelled loops is persisted alongside.
+
 ### `[auto_continue]`
 
 Auto-continue detects when Claude Code exits after receiving tool results without processing them (upstream bugs [#34142](https://github.com/anthropics/claude-code/issues/34142), [#30333](https://github.com/anthropics/claude-code/issues/30333)) and automatically resumes the session. Detection is based on a protocol invariant: normal sessions always end with `last_event_type=result`, while premature exits show `last_event_type=user`.
@@ -324,11 +369,15 @@ Runtime security knobs. Defaults are safe — operators only flip these when inv
     ```toml
     [security]
     env_audit = true
+    env_extra_allow = ["OP_SERVICE_ACCOUNT_TOKEN", "DOPPLER_TOKEN"]
+    env_extra_prefix_allow = ["VAULT_", "INFISICAL_"]
     ```
 
 | Key | Type | Default | Notes |
 |-----|------|---------|-------|
 | `env_audit` | bool | `true` | One-shot `/proc/<claude_pid>/environ` sample on first `system.init` ([#361](https://github.com/littlebearapps/untether/issues/361)). Emits `claude.env_audit.leaked_var` WARNING per non-allowlisted name observed (dedup per session per name). Reuses `utils/env_policy.is_allowed`. Linux-only — silently no-ops elsewhere or when /proc is unreadable. Set `false` to opt out (e.g. on hardened hosts where `/proc/<pid>/environ` reads are sensitive). The companion `env -i` wrap on Claude exec ([#361](https://github.com/littlebearapps/untether/issues/361)) is always on and not configurable. |
+| `env_extra_allow` | list[str] | `[]` | Per-deployment exact-match additions to the engine-subprocess env allowlist ([#409](https://github.com/littlebearapps/untether/issues/409)). Use for credential-manager tokens that aren't in the global defaults — e.g. `["OP_SERVICE_ACCOUNT_TOKEN", "DOPPLER_TOKEN", "INFISICAL_TOKEN"]`. Each entry must match `[A-Z_][A-Z0-9_]*` (uppercase, digits, underscore; cannot start with a digit). Empty / whitespace / lowercase entries are rejected at config-load time. Currently honoured by the Claude and Pi runners. The audit (`env_audit`) honours these too, so user-allowed names aren't false-flagged as leaks. Untether emits one `env_policy.user_extension` INFO log per process at first runner spawn so the addition is visible in journalctl. |
+| `env_extra_prefix_allow` | list[str] | `[]` | Like `env_extra_allow` but for name *prefixes* — convenient for credential-manager families where many vars share a prefix. Examples: `["VAULT_"]` admits `VAULT_TOKEN`, `VAULT_ADDR`, `VAULT_NAMESPACE`. Each entry must match the same env-var name shape as `env_extra_allow`. |
 
 ## Engine-specific config tables
 
@@ -363,6 +412,7 @@ here; plugin engines should document their own keys.
 |-----|------|---------|-------|
 | `model` | string | (unset) | Optional model override. |
 | `allowed_tools` | string[] | `["Bash", "Read", "Edit", "Write"]` | Auto-approve tool rules. |
+| `extra_args` | string[] | `[]` | Extra CLI args passed to `claude` (e.g. `["--chrome"]` to opt into the Claude-in-Chrome extension). Flags Untether manages internally (`-p`, `--print`, `--output-format`, `--input-format`, `--resume`/`-r`, `--continue`/`-c`, `--permission-mode`, `--permission-prompt-tool`) are rejected at config-load. |
 | `dangerously_skip_permissions` | bool | `false` | Skip Claude Code permissions prompts. |
 | `use_api_billing` | bool | `false` | Keep `ANTHROPIC_API_KEY` for API billing. |
 
@@ -371,6 +421,7 @@ here; plugin engines should document their own keys.
     ```sh
     untether config set claude.model "claude-sonnet-4-5-20250929"
     untether config set claude.allowed_tools '["Bash", "Read", "Edit", "Write"]'
+    untether config set claude.extra_args '["--chrome"]'
     untether config set claude.dangerously_skip_permissions false
     untether config set claude.use_api_billing false
     ```
@@ -381,6 +432,7 @@ here; plugin engines should document their own keys.
     [claude]
     model = "claude-sonnet-4-5-20250929"
     allowed_tools = ["Bash", "Read", "Edit", "Write"]
+    extra_args = ["--chrome"]    # e.g. opt into Claude-in-Chrome
     dangerously_skip_permissions = false
     use_api_billing = false
     ```
@@ -434,11 +486,13 @@ here; plugin engines should document their own keys.
 | Key | Type | Default | Notes |
 |-----|------|---------|-------|
 | `model` | string | (unset) | Optional model override, passed as `--model`. |
+| `skip_trust` | bool | `true` | Pass `--skip-trust` so headless runs work outside `~/.gemini/trustedFolders.json` ([#471](https://github.com/littlebearapps/untether/issues/471)). Gemini CLI rejects runs from any directory not in the trust list — even with `--approval-mode yolo` — and there is no interactive prompt path in headless usage. Set `false` to enforce Gemini's project-local extension/MCP trust gate. |
 
 === "untether config"
 
     ```sh
     untether config set gemini.model "gemini-2.5-pro"
+    untether config set gemini.skip_trust true
     ```
 
 === "toml"
@@ -446,6 +500,7 @@ here; plugin engines should document their own keys.
     ```toml
     [gemini]
     model = "gemini-2.5-pro"
+    skip_trust = true
     ```
 
 !!! note "Approval mode"
@@ -457,7 +512,7 @@ here; plugin engines should document their own keys.
 |-----|------|---------|-------|
 | `mode` | string | (unset) | Execution mode, passed as `--mode`. Values: `deep`, `free`, `rush`, `smart`. |
 | `model` | string | (unset) | Display label shown in the message footer. Overridden by `mode` if both are set. |
-| `dangerously_allow_all` | bool | `true` | Pass `--dangerously-allow-all` to skip permission prompts. |
+| `dangerously_allow_all` | bool | `false` | Pass `--dangerously-allow-all` to skip AMP's permission prompts. **Default flipped to `false` in v0.35.3** ([#206](https://github.com/littlebearapps/untether/issues/206)) — set to `true` only if you specifically want AMP runs without its built-in permission system. Untether's own permission layer (when configured) remains the primary control. |
 | `stream_json_input` | bool | `false` | Pass `--stream-json-input` for stdin-based prompt delivery. |
 
 === "untether config"
diff --git a/docs/reference/env-vars.md b/docs/reference/env-vars.md
index 5d8c4525..bde2773b 100644
--- a/docs/reference/env-vars.md
+++ b/docs/reference/env-vars.md
@@ -32,16 +32,28 @@ These variables are set automatically by Untether in the engine subprocess envir
 | Variable | Set by | Description |
 |----------|--------|-------------|
 | `UNTETHER_SESSION` | Claude runner | Set to `1` for all Claude Code subprocess invocations. Enables Claude Code plugins to detect Untether sessions and adjust behaviour — for example, skipping blocking Stop hooks that would displace user-requested content in Telegram. |
-| `CLAUDE_STREAM_IDLE_TIMEOUT_MS` | Claude runner | Claude Code's stdout idle timeout. Default raised to `300000` (5 min) in v0.35.2 ([#342](https://github.com/littlebearapps/untether/issues/342)) — matches undici's idle-body timeout. The old 60 s default killed long-thinking runs. Set explicitly in the Untether environment to override. |
+| `CLAUDE_STREAM_IDLE_TIMEOUT_MS` | Claude runner | Claude Code's stdout idle timeout. Default raised to `300000` (5 min) in v0.35.2 ([#342](https://github.com/littlebearapps/untether/issues/342)) — matches undici's idle-body timeout. The old 60 s default killed long-thinking runs. **As of v0.35.3 ([#438](https://github.com/littlebearapps/untether/issues/438))**, this is preferably set via `[watchdog] claude_stream_idle_timeout_ms` in `untether.toml` (range 30 s – 30 min). Shell-set `CLAUDE_STREAM_IDLE_TIMEOUT_MS` still wins via `setdefault`. Failures with `API Error: Stream idle timeout - partial response received` now classify as Type A (mid-generation — raising helps) or Type B (cold-start zero-byte — raising does NOT help; upstream API outage). |
 
 !!! note "Not a security concern"
     `UNTETHER_SESSION` is a simple signal variable, not a credential or secret. It tells Claude Code plugins that the session is running via Telegram so they can avoid interfering with Untether's single-message output model. Plugins like [PitchDocs](https://github.com/littlebearapps/lba-plugins) check for this variable and skip blocking hooks that would otherwise consume the final response with meta-commentary instead of the user's requested content. See the [PitchDocs interference audit](../audits/pitchdocs-context-guard-interference.md) for the full analysis.
 
 ## Env allowlist (Claude/Pi)
 
-As of v0.35.2, arbitrary process env vars are **not** forwarded to Claude/Pi subprocesses. Only an internal allowlist (things like `PATH`, `HOME`, `LANG`, Anthropic/OpenAI/Pi credentials, and a small set of CLI-specific knobs including `CLAUDE_STREAM_IDLE_TIMEOUT_MS`, `MCP_TOOL_TIMEOUT`, `MAX_MCP_OUTPUT_TOKENS`) is passed through. ([#198](https://github.com/littlebearapps/untether/issues/198))
+As of v0.35.2, arbitrary process env vars are **not** forwarded to Claude/Pi subprocesses. Only an internal allowlist (things like `PATH`, `HOME`, `LANG`, Anthropic/OpenAI/Pi credentials, `BWS_ACCESS_TOKEN` (added as a default in v0.35.3), and a small set of CLI-specific knobs including `CLAUDE_STREAM_IDLE_TIMEOUT_MS`, `MCP_TOOL_TIMEOUT`, `MAX_MCP_OUTPUT_TOKENS`) is passed through. ([#198](https://github.com/littlebearapps/untether/issues/198))
 
 When `[security] env_audit = true` (default — see [config reference](config.md#security)), any non-allowlisted var observed in the parent process logs a `claude.env_audit.leaked_var` WARNING and the subprocess spawns under `env -i KEY=VAL …` so the leak is actually scrubbed rather than just reported. ([#361](https://github.com/littlebearapps/untether/issues/361))
 
-If a plugin or MCP server depends on a specific variable, add it to the allowlist (open an issue) or set `[security] env_audit = false` to restore legacy behaviour.
+### Extending the allowlist (v0.35.3+)
+
+If a plugin or MCP server depends on a specific variable, add it to the allowlist via TOML config — no fork, no re-install ([#409](https://github.com/littlebearapps/untether/issues/409)):
+
+```toml title="~/.untether/untether.toml"
+[security]
+env_extra_allow = ["OP_SERVICE_ACCOUNT_TOKEN", "DOPPLER_TOKEN"]   # exact names
+env_extra_prefix_allow = ["VAULT_", "INFISICAL_"]                  # families
+```
+
+Names must match `[A-Z_][A-Z0-9_]*`. Untether emits one `env_policy.user_extension` INFO log per process at first runner spawn so the addition is visible in `journalctl`. The runtime audit also honours these so user-allowed names aren't false-flagged as leaks. See [security guide](../how-to/security.md#engine-subprocess-env-allowlist) for the full discussion.
+
+If you'd rather the new variable ship as a default for every Untether user, open a PR adding it to `_EXACT_ALLOW` / `_PREFIX_ALLOW` in `src/untether/utils/env_policy.py`. Set `[security] env_audit = false` to restore the legacy unconditional-pass-through behaviour (not recommended).
 
diff --git a/docs/reference/integration-testing.md b/docs/reference/integration-testing.md
index 2cb38385..4778208a 100644
--- a/docs/reference/integration-testing.md
+++ b/docs/reference/integration-testing.md
@@ -144,7 +144,7 @@ Tests for per-chat and per-topic settings that affect run behaviour. Use forum t
 |---|------|-------------|----------------|---------|
 | O1 | **Engine override** | `/agent set gemini`, then send a plain prompt (no directive) | Gemini runs, footer shows Gemini model | Per-chat engine default, override hierarchy |
 | O2 | **Reasoning level** | `/config` → Reasoning → enable, then send a prompt | Reasoning model used, footer reflects it | Reasoning flag in build_args |
-| O3 | **Trigger mode** | `/trigger mentions` in group, send plain text, then `@bot do something` | Plain text ignored, @mention triggers run | Trigger mode filtering |
+| O3 | **Listen mode** | `/listen mentions` in group, send plain text, then `@bot do something` | Plain text ignored, @mention triggers run | Listen mode filtering (renamed from `/trigger` in v0.35.3 [#297](https://github.com/littlebearapps/untether/issues/297); deprecated alias still works) |
 | O4 | **Ask mode toggle** | `/config` → Ask → off, send prompt that would trigger AskUserQuestion | Question auto-denied instead of shown | Ask mode auto-deny path |
 | O5 | **Context set** | `/ctx set test-claude main`, send prompt | Run uses test-claude project on main branch | Context resolution, project switching |
 | O6 | **Context clear** | `/ctx clear`, send prompt | Falls back to chat/project default | Context fallback chain |
@@ -197,7 +197,7 @@ Run quickly to verify all commands respond.
 | Q9 | `/stats` | Session statistics or empty | 1s |
 | Q10 | `/ctx` | Current context or "none set" | 1s |
 | Q11 | `/agent` | Current engine override or default | 1s |
-| Q12 | `/trigger` | Current trigger mode | 1s |
+| Q12 | `/listen` | Current listen mode | 1s |
 | Q13 | `/file` | Usage help or file browser | 1s |
 | Q14 | `/at 60s smoke test` | "⏳ Scheduled" confirmation; run fires after ~60s | 70s |
 | Q15 | `/at 5m test` then `/cancel` | Scheduling confirmation; cancel drops pending; no run after 5m | 10s (skip 5m wait) |
diff --git a/docs/reference/runners/amp/runner.md b/docs/reference/runners/amp/runner.md
index c133eee6..f18853e8 100644
--- a/docs/reference/runners/amp/runner.md
+++ b/docs/reference/runners/amp/runner.md
@@ -43,12 +43,12 @@ Notes:
 The runner invokes:
 
 ```text
-amp --dangerously-allow-all --mode <mode> --model <model> -x --stream-json <prompt>
+amp [--dangerously-allow-all] --mode <mode> --model <model> -x --stream-json <prompt>
 ```
 
 Flags:
 
-* `--dangerously-allow-all` — auto-approve all tool calls (default, configurable)
+* `--dangerously-allow-all` — auto-approve all of AMP's tool calls. **Default flipped to `false` in v0.35.3** ([#206](https://github.com/littlebearapps/untether/issues/206)); set `[amp] dangerously_allow_all = true` to enable.
 * `--mode <mode>` — optional (`deep|free|rush|smart`)
 * `--model <model>` — optional, from config or `/config` override
 * `-x` — execute mode (non-interactive)
@@ -60,7 +60,7 @@ Prompts starting with `-` are space-prefixed via `sanitize_prompt()` (base runne
 For resumed sessions:
 
 ```text
-amp threads continue <thread-id> --dangerously-allow-all -x --stream-json <prompt>
+amp threads continue <thread-id> [--dangerously-allow-all] -x --stream-json <prompt>
 ```
 
 ---
@@ -73,7 +73,7 @@ amp threads continue <thread-id> --dangerously-allow-all -x --stream-json <promp
     untether config set default_engine "amp"
     untether config set amp.model "claude-sonnet-4-6"
     untether config set amp.mode "smart"
-    untether config set amp.dangerously_allow_all true
+    untether config set amp.dangerously_allow_all false
     ```
 
 === "toml"
@@ -86,14 +86,14 @@ amp threads continue <thread-id> --dangerously-allow-all -x --stream-json <promp
     [amp]
     model = "claude-sonnet-4-6"       # optional; passed as --model
     mode = "smart"                     # optional; deep|free|rush|smart
-    dangerously_allow_all = true       # default: true
+    dangerously_allow_all = false      # default: false (changed in v0.35.3 #206)
     stream_json_input = false          # default: false; passes --stream-json-input
     ```
 
 Notes:
 
 * `mode` controls model selection, system prompt, and tool availability within AMP.
-* `dangerously_allow_all` defaults to `true` since Untether runs headless.
+* `dangerously_allow_all` defaults to `false` as of v0.35.3 ([#206](https://github.com/littlebearapps/untether/issues/206)) — opt in only if you specifically want AMP runs without its built-in permission system. Untether's own permission layer remains the primary control.
 * `stream_json_input` enables `--stream-json-input` for stdin streaming. This is preliminary plumbing — the interactive control flow (approve/deny via Telegram) is not yet wired.
 
 ---
@@ -107,7 +107,7 @@ Exposes `BACKEND = EngineBackend(id="amp", build_runner=build_runner, install_cm
 #### Runner invocation
 
 ```text
-amp [threads continue <thread-id>] --dangerously-allow-all [--mode <mode>] [--model <model>] -x --stream-json [--stream-json-input] <prompt>
+amp [threads continue <thread-id>] [--dangerously-allow-all] [--mode <mode>] [--model <model>] -x --stream-json [--stream-json-input] <prompt>
 ```
 
 #### Event translation
diff --git a/docs/reference/runners/amp/untether-events.md b/docs/reference/runners/amp/untether-events.md
index b99b6b82..fcc419fc 100644
--- a/docs/reference/runners/amp/untether-events.md
+++ b/docs/reference/runners/amp/untether-events.md
@@ -185,7 +185,7 @@ Returns `None` if no usage data was accumulated.
     ```sh
     untether config set amp.model "claude-sonnet-4-6"
     untether config set amp.mode "smart"
-    untether config set amp.dangerously_allow_all true
+    untether config set amp.dangerously_allow_all false
     ```
 
 === "toml"
@@ -194,5 +194,5 @@ Returns `None` if no usage data was accumulated.
     [amp]
     model = "claude-sonnet-4-6"       # optional
     mode = "smart"                     # optional: deep|free|rush|smart
-    dangerously_allow_all = true       # default: true
+    dangerously_allow_all = false      # default: false (flipped in v0.35.3 — #206)
     ```
diff --git a/docs/reference/runners/claude/runner.md b/docs/reference/runners/claude/runner.md
index 8dce3aa3..b06535de 100644
--- a/docs/reference/runners/claude/runner.md
+++ b/docs/reference/runners/claude/runner.md
@@ -78,6 +78,7 @@ Recommended v1 schema:
     untether config set default_engine "claude"
     untether config set claude.model "claude-sonnet-4-5-20250929"
     untether config set claude.allowed_tools '["Bash", "Read", "Edit", "Write"]'
+    untether config set claude.extra_args '["--chrome"]'
     untether config set claude.dangerously_skip_permissions false
     untether config set claude.use_api_billing false
     ```
@@ -93,6 +94,7 @@ Recommended v1 schema:
     model = "claude-sonnet-4-5-20250929" # optional (Claude Code supports model override in settings too)
     permission_mode = "auto"             # optional: "plan", "auto", or "acceptEdits"
     allowed_tools = ["Bash", "Read", "Edit", "Write"] # optional but strongly recommended for automation
+    extra_args = ["--chrome"]           # optional: extra upstream CLI flags (e.g. --chrome opts into Claude-in-Chrome)
     dangerously_skip_permissions = false # optional (high risk; prefer sandbox use only)
     use_api_billing = false             # optional (keep ANTHROPIC_API_KEY for API billing)
     ```
@@ -102,8 +104,9 @@ Notes:
 * `--allowedTools` exists specifically to auto-approve tools in programmatic runs. ([Claude Code][1])
 * Claude Code tools (Bash/Edit/Write/WebSearch/etc.) and whether permission is required are documented. ([Claude Code][2])
 * If `allowed_tools` is omitted, Untether defaults to `["Bash", "Read", "Edit", "Write"]`.
-* Untether reads `model`, `permission_mode`, `allowed_tools`, `dangerously_skip_permissions`, and `use_api_billing` from `[claude]`.
+* Untether reads `model`, `permission_mode`, `allowed_tools`, `extra_args`, `dangerously_skip_permissions`, and `use_api_billing` from `[claude]`.
 * `permission_mode = "auto"` uses `--permission-mode plan` on the CLI but auto-approves ExitPlanMode requests without showing Telegram buttons. Can also be set per chat via `/planmode auto`.
+* `extra_args` lets you pass additional upstream `claude` CLI flags that Untether doesn't expose directly — for example `["--chrome"]` opts into the Claude-in-Chrome extension (otherwise gated off by Claude Code 2.1.x), or `["--strict-mcp-config"]` / `["--mcp-config", "path"]` for MCP tweaks. Flags Untether manages internally (`-p`, `--print`, `--output-format`, `--input-format`, `--resume`/`-r`, `--continue`/`-c`, `--permission-mode`, `--permission-prompt-tool`) are rejected at config-load with a `ConfigError`. Mirrors `codex.extra_args` and `pi.extra_args`.
 * By default Untether strips `ANTHROPIC_API_KEY` from the subprocess environment so Claude Code uses subscription billing. Set `use_api_billing = true` to keep the key.
 
 ---
@@ -117,7 +120,7 @@ The Claude runner modifies the subprocess environment before spawning `claude`:
 | `UNTETHER_SESSION` | Set to `1`. Signals to Claude Code plugins (hooks, rules, agents) that the session is running via Untether/Telegram. Plugins can check `[ -n "${UNTETHER_SESSION:-}" ]` in shell hooks to adjust behaviour — e.g. skip blocking Stop hooks that would displace the user's requested content in Telegram's single-message output. See [PitchDocs](https://github.com/littlebearapps/lba-plugins) for a reference implementation. |
 | `ANTHROPIC_API_KEY` | Stripped from the environment by default so Claude Code uses subscription billing. Set `use_api_billing = true` in `[claude]` config to keep the key and use API billing instead. |
 | `CLAUDE_ENABLE_STREAM_WATCHDOG` | Set to `1` via `setdefault` ([#322](https://github.com/littlebearapps/untether/issues/322)). Enables the upstream stream watchdog so Claude Code aborts cleanly on SSE idle timeout instead of hanging. User overrides via shell env still win. |
-| `CLAUDE_STREAM_IDLE_TIMEOUT_MS` | Set to `300000` (5 min) via `setdefault` ([#342](https://github.com/littlebearapps/untether/issues/342)). Matches the undici idle-body timeout that motivated [#322](https://github.com/littlebearapps/untether/issues/322) and Untether's `[watchdog] stuck_after_tool_result_timeout` default. The earlier 60s value tripped on `opus · max` legitimate chain-of-thought windows. |
+| `CLAUDE_STREAM_IDLE_TIMEOUT_MS` | Set to `300000` (5 min) via `setdefault` ([#342](https://github.com/littlebearapps/untether/issues/342)). Matches the undici idle-body timeout that motivated [#322](https://github.com/littlebearapps/untether/issues/322) and Untether's `[watchdog] stuck_after_tool_result_timeout` default. As of v0.35.3 ([#438](https://github.com/littlebearapps/untether/issues/438)) this default is user-configurable via `[watchdog] claude_stream_idle_timeout_ms` (range 30 s – 30 min) for deployments that hit upstream Anthropic API stalls on long opus 4.7 1M plan-mode generations. Shell-set values still win via `setdefault`. The earlier 60 s value tripped on `opus · max` legitimate chain-of-thought windows. |
 | `MCP_TOOL_TIMEOUT` | Set to `120000` (2 min) via `setdefault` ([#322](https://github.com/littlebearapps/untether/issues/322)). |
 | `MAX_MCP_OUTPUT_TOKENS` | Set to `12000` via `setdefault` ([#322](https://github.com/littlebearapps/untether/issues/322)). |
 
@@ -135,6 +138,31 @@ A companion runtime audit (gated by `[security] env_audit = true`, default true)
 
 `--effort` accepts `low`, `medium`, `high`, `xhigh`, `max`. The `xhigh` level was added in v0.35.2 ([#351](https://github.com/littlebearapps/untether/issues/351)) for Claude Code CLI v2.1.114+ — it sits between `high` and `max` and is exposed in `/config → 🧠 Effort`. Set per-chat via the inline menu or pin per-engine via `[engines.claude] reasoning = "xhigh"`.
 
+### Post-result idle timeout + "✓ turn complete" hint ([#333](https://github.com/littlebearapps/untether/issues/333))
+
+After Claude Code emits its final `result` event the bidirectional CLI can sit alive for up to ~36 min before exiting on its own, leaving Untether's progress message looking stuck. The runner now closes that gap two ways:
+
+1. **Footer marker** — every successful `result` event arms a supplementary `StartedEvent` with `meta={"complete": "✓ turn complete"}`, which `markdown.format_meta_line` renders alongside model / effort / permission / trigger so the user sees the turn boundary immediately. Errored results don't emit the hint (no false "complete" tag on a failure).
+2. **Server-side timer** — `_post_result_idle_watchdog` arms `result_received_at` and closes stdin (`this_proc_stdin.aclose()`) once the deadline passes, after which the CLI hits stdin EOF and exits cleanly (rc=0). Claude's auto-continue safety gate already excludes `last_event_type == "result"` so the clean exit will not phantom-resume the session.
+
+Configure via `[watchdog]`:
+
+* `post_result_idle_enabled` — default `true`. Explicit kill-switch.
+* `post_result_idle_timeout` — seconds (default `600`, range 30–3600).
+
+Approval-state guard: if `_REQUEST_TO_SESSION` or `_PENDING_ASK_REQUESTS` has live entries for the session the timer re-arms instead of closing — prevents orphaning a button-click `control_response` mid-flight.
+
+Two structlog events for ops: `claude.post_result_idle.deferred` (approval guard fired) and `claude.post_result_idle.closing_stdin` (deadline passed cleanly).
+
+### `Stream idle timeout - partial response` classification ([#438](https://github.com/littlebearapps/untether/issues/438))
+
+When Claude fails with `API Error: Stream idle timeout - partial response received`, the runner's `_extract_error` now appends a one-line classification to the user-visible message:
+
+* **Type-A (mid-generation)** — `num_turns ≥ 1 && duration_api_ms > 0`. Suggests raising `[watchdog] claude_stream_idle_timeout_ms` to ride out longer SSE silences (typical for opus 4.7 1M plan-mode generations).
+* **Type-B (cold-start zero-byte stall)** — `num_turns ≤ 1 && duration_api_ms == 0`. Tells the user explicitly that raising the timeout will **not** help — it's an upstream Anthropic API outage, not a local watchdog miscalibration.
+
+Auto-retry on Type-A is deferred to v0.35.4 pending upstream Anthropic stabilisation.
+
 ### `rate_limit_event` surfacing ([#349](https://github.com/littlebearapps/untether/issues/349))
 
 When Anthropic throttles the API, Claude Code emits a `rate_limit_event` JSONL message. The runner translates this to a visible `note`-kind action rendered as `⏳ Rate limited — retrying in Xs` in Telegram (previously the runner returned an empty list and the session appeared to hang). `ClaudeStreamState.rate_limit_total_s` accumulates wait time across the session for future cost-footer annotation; structured `claude.rate_limit_event` logs `retry_after_s`, `count`, and `cumulative_s` for triage.
diff --git a/docs/reference/runners/claude/stream-json-cheatsheet.md b/docs/reference/runners/claude/stream-json-cheatsheet.md
index d9a8a858..dff80cbe 100644
--- a/docs/reference/runners/claude/stream-json-cheatsheet.md
+++ b/docs/reference/runners/claude/stream-json-cheatsheet.md
@@ -136,6 +136,20 @@ Fields:
 {"type":"tool_use","id":"toolu_1","name":"Bash","input":{"command":"ls -la"}}
 ```
 
+#### `ScheduleWakeup` (session-scoped scheduling)
+
+Claude Code 2.1.x emits `ScheduleWakeup` `tool_use` blocks when the model parks itself for a delay (`/loop`'s no-interval dynamic mode and similar). Untether observes these for [Loop mode](../../../how-to/inline-settings.md#loop-mode) and the long-running tool tail.
+
+```json
+{"type":"tool_use","id":"toolu_3","name":"ScheduleWakeup","input":{"delaySeconds":300,"reason":"build check","prompt":"check if the build finished"}}
+```
+
+* `delaySeconds` (int, 60–3600) — wall-clock delay before wakeup. Untether reads this field for countdown rendering ([#481](https://github.com/littlebearapps/untether/issues/481) fixed; pre-rc7 reads `delay_ms`/`timeout_ms` were always 0.0 in production).
+* `reason` (string) — short human label rendered in verbose mode (`→ fires in 4m 12s · "build check"`).
+* `prompt` (string) — the prompt the model wants to fire on wakeup (loop iteration body).
+
+`CronCreate` follows the same shape with a `cron` field (5-field expression) instead of `delaySeconds`. The Loop observer parses `cron` (not `cron_expression`) and `id` (not `taskId`/`cronId`); upstream 8-character cron IDs bind via `\bjob ([0-9a-f]{8})\b` from the assistant text.
+
 ### Tool result
 String content:
 ```json
diff --git a/docs/reference/runners/claude/untether-events.md b/docs/reference/runners/claude/untether-events.md
index 987064df..e287b803 100644
--- a/docs/reference/runners/claude/untether-events.md
+++ b/docs/reference/runners/claude/untether-events.md
@@ -151,6 +151,10 @@ The terminal event looks like:
 - Emit exactly one `completed` event; ignore any trailing JSON lines afterward.
   No idle-timeout completion is used.
 
+#### Supplementary `started` event after `result` (`✓ turn complete`)
+
+Every successful `result` (i.e. `is_error=false`) MAY also emit a supplementary `started` event carrying late-arriving meta — `meta={"complete": "✓ turn complete"}` ([#333](https://github.com/littlebearapps/untether/issues/333)). This is the supported pattern for late-arriving meta documented in `runner-development.md`: `ProgressTracker.note_event` merges meta idempotently so the marker shows up in the footer (`format_meta_line`) alongside model / effort / permission / trigger without duplicating the StartedEvent. Errored results do **not** emit the marker — no false "complete" tag on a failure.
+
 #### Permission denials
 
 > **Not yet implemented.** The upstream Claude Code CLI may include
diff --git a/docs/reference/runners/gemini/runner.md b/docs/reference/runners/gemini/runner.md
index 35c92980..ac921c87 100644
--- a/docs/reference/runners/gemini/runner.md
+++ b/docs/reference/runners/gemini/runner.md
@@ -43,7 +43,7 @@ Notes:
 The runner invokes:
 
 ```text
-gemini -p --output-format stream-json --model <model> --prompt=<prompt>
+gemini -p --output-format stream-json --skip-trust --model <model> --prompt=<prompt>
 ```
 
 Flags:
@@ -54,6 +54,7 @@ Flags:
 * `--prompt=<value>` — prompt bound directly to flag (prevents injection when prompt starts with `-`)
 * `--resume <session_id>` — when resuming a session
 * `--approval-mode <mode>` — defaults to `yolo` (full access) when no override is set; configurable via `/config` or `permission_mode` run option
+* `--skip-trust` — passed by **default** as of v0.35.3 ([#471](https://github.com/littlebearapps/untether/issues/471)) so headless runs work outside `~/.gemini/trustedFolders.json`. Gemini CLI rejects runs from any directory not in the trust list — even with `--approval-mode yolo` — and there is no interactive prompt path in headless usage, so projects outside the trust list previously failed silently before any agent output. Set `[gemini] skip_trust = false` in `untether.toml` to opt out (security-conscious operators who want Gemini's project-local extension/MCP trust gate enforced).
 
 ---
 
@@ -75,6 +76,7 @@ Flags:
 
     [gemini]
     model = "gemini-2.5-pro"   # optional; passed as --model
+    skip_trust = true          # optional; default true — opt out to enforce trustedFolders.json
     ```
 
 Notes:
diff --git a/docs/reference/runners/pi/runner.md b/docs/reference/runners/pi/runner.md
index 221c88e3..129fdd73 100644
--- a/docs/reference/runners/pi/runner.md
+++ b/docs/reference/runners/pi/runner.md
@@ -85,6 +85,7 @@ Notes:
 * `extra_args` lets you pass new Pi flags without changing Untether.
 * Session files are stored under Pi's default session dir:
   `~/.pi/agent/sessions/--<cwd>--` (with path separators replaced by `-`).
+* The Pi runner explicitly creates the session dir with `0o700` (rwx------) and chmods any pre-existing dir to the same mode ([#207](https://github.com/littlebearapps/untether/issues/207)) so other users on a shared host can't read Pi session JSONL.
 
 ---
 
diff --git a/docs/reference/specification.md b/docs/reference/specification.md
index 3be14318..9131ddb0 100644
--- a/docs/reference/specification.md
+++ b/docs/reference/specification.md
@@ -1,4 +1,4 @@
-# Untether Specification v0.35.1 [2026-04-15]
+# Untether Specification v0.35.3 [2026-05-08]
 
 This document is **normative**. The words **MUST**, **SHOULD**, and **MAY** express requirements.
 
diff --git a/docs/reference/transports/telegram.md b/docs/reference/transports/telegram.md
index 43f9dc9b..1813b33f 100644
--- a/docs/reference/transports/telegram.md
+++ b/docs/reference/transports/telegram.md
@@ -74,7 +74,7 @@ Explicit invocation includes any of:
 - `@botname` mention in the message.
 - `/<engine-id>` or `/<project-alias>` as the first token.
 - Replying to a bot message.
-- Built-in or plugin slash commands (for example `/agent`, `/model`, `/reasoning`, `/file`, `/trigger`).
+- Built-in or plugin slash commands (for example `/agent`, `/model`, `/reasoning`, `/file`, `/listen`).
 
 Note: In forum topics, some Telegram clients include `reply_to_message` on every
 message, pointing at the topic’s root service message (`message_id ==
@@ -83,12 +83,14 @@ explicit replies, so they do not trigger mentions-only mode.
 
 Commands:
 
-- `/trigger` shows the current mode and defaults.
-- `/trigger mentions` restricts runs to explicit invocations.
-- `/trigger all` restores the default behavior.
-- `/trigger clear` clears a topic override (topics only).
+- `/listen` shows the current mode and defaults.
+- `/listen mentions` restricts runs to explicit invocations.
+- `/listen all` restores the default behavior.
+- `/listen clear` clears a topic override (topics only).
 
-In group chats, changing trigger mode requires the sender to be an admin.
+`/trigger` continues to work as a deprecated alias for one release cycle ([#297](https://github.com/littlebearapps/untether/issues/297)) and prints a one-line deprecation notice on each invocation.
+
+In group chats, changing listen mode requires the sender to be an admin.
 
 State is stored in `telegram_chat_prefs_state.json` (chat default) and
 `telegram_topics_state.json` (topic overrides) alongside the config file.
diff --git a/docs/reference/triggers/triggers.md b/docs/reference/triggers/triggers.md
index 8a7adbc2..4a379b87 100644
--- a/docs/reference/triggers/triggers.md
+++ b/docs/reference/triggers/triggers.md
@@ -494,7 +494,7 @@ the filesystem context.
 
 ## Trigger visibility
 
-!!! info "New in v0.35.1"
+!!! info "Tier 1 in v0.35.1, Tier 2/3 expanded in v0.35.3"
 
 ### Per-chat `/ping` indicator
 
@@ -511,11 +511,17 @@ If multiple triggers target the chat, the indicator shows counts instead of the
 ⏰ triggers: 2 crons, 1 webhook
 ```
 
+While master pause is active (see [Pause/Resume](#pause-and-resume)), `/ping` switches to:
+
+```
+⏸ triggers paused: 2 crons, 1 webhook (suspended)
+```
+
 The indicator is per-chat — only triggers whose `chat_id` matches the current chat appear. Triggers that omit `chat_id` (and therefore fall back to the transport's default `chat_id`) show for that chat only.
 
 ### Meta footer
 
-Runs initiated by a cron or webhook show provenance in the meta footer alongside model and mode:
+Runs initiated by a cron, webhook, or `/at` show provenance in the meta footer alongside model and mode:
 
 ```
 🏷 opus 4.6 · plan · ⏰ cron:daily-review
@@ -523,6 +529,28 @@ Runs initiated by a cron or webhook show provenance in the meta footer alongside
 
 - `⏰ cron:<id>` for cron-initiated runs
 - `⚡ webhook:<id>` for webhook-initiated runs
+- `⏰ at:<token>` for `/at <duration>` one-shot delayed runs ([#271](https://github.com/littlebearapps/untether/issues/271) follow-up)
+
+### `/config` → 📡 Triggers page (Tier 2)
+
+`/config` → **📡 Triggers** (`config:tg`) lists every cron and webhook configured for the current chat ([#271](https://github.com/littlebearapps/untether/issues/271) Tier 2):
+
+- **Crons**: human-readable `describe_cron(schedule, timezone)`, project, engine, last-fired relative time
+- **Webhooks**: path, auth scheme, project, engine, last-fired
+
+Lists are scoped to the current chat (using `crons_for_chat` / `webhooks_for_chat` with the bridge `default_chat_id` fallback), capped at 10 entries with a `…and N more (see untether.toml)` overflow marker.
+
+The same page hosts the master [Pause/Resume](#pause-and-resume) toggle.
+
+### `/stats` triggered/manual breakdown (Tier 3)
+
+`/stats` appends `(N triggered, M manual)` to per-engine lines and the totals row when at least one count is nonzero ([#271](https://github.com/littlebearapps/untether/issues/271) Tier 3):
+
+```
+claude: 12 runs (8 triggered, 4 manual)
+```
+
+Triggered counts include cron, webhook, and `/at` fires. Backed by a new persistent JSON history store at `<config_path>.with_name("triggers_history.json")` recording wall time after every successful cron/webhook/action dispatch. Recording is best-effort — a transient disk failure logs `triggers.history.write_failed` and swallows so it can't break the cron loop or webhook server. Renaming a trigger ID in TOML leaves a stale entry that operators can manually delete (no auto-prune to avoid losing data on transient TOML errors).
 
 ### Human-friendly cron descriptions
 
@@ -562,8 +590,36 @@ The webhook server exposes a `GET /health` endpoint that returns:
 {"status": "ok", "webhooks": 2}
 ```
 
+While master pause is active (see [Pause/Resume](#pause-and-resume)) the same endpoint returns:
+
+```json
+{"status": "paused", "paused": true, "webhooks": 2}
+```
+
+External monitors can use the `paused` field to distinguish "paused but up" from "down" — the bot is healthy and reachable, just not dispatching trigger work.
+
 Use this for uptime monitoring or reverse proxy health checks.
 
+## Pause and resume
+
+`TriggerManager` exposes a master pause toggle ([#294](https://github.com/littlebearapps/untether/issues/294)) that gates **both** crons and webhooks at once:
+
+- **Cron loop**: skips its tick while paused. `run_once` crons are not consumed during the pause and fire on the next matching tick after resume.
+- **Webhook server**: returns `503 triggers paused` with `Retry-After: 60` instead of dispatching. Auth, rate-limit, and event-filter checks still run before the 503 so an unauthenticated probe still gets `401`, not `503`.
+- **`/health`**: surfaces `{"status": "paused", "paused": true}`.
+- **`/ping`**: switches to `⏸ triggers paused: … (suspended)`.
+
+### Toggling
+
+Pause/resume is wired into `/config` two ways:
+
+1. **Home-page button row** — appears at the bottom of the `/config` home page only when triggers are configured. One-tap toggle.
+2. **Dedicated 📡 Triggers page** (`config:tg`) — shows current state and counts, with a Pause/Resume button at the top. The same page lists per-chat crons and webhooks.
+
+### Persistence
+
+Pause is **in-memory only** — restart auto-resumes (the safe default). If you need a durable shutoff, set `[triggers] enabled = false` in `untether.toml`, which survives restarts. Pause is for "stop firing for the next half hour while I deploy" not "permanently disable triggers".
+
 ## Testing webhooks
 
 Test a webhook locally with curl:
@@ -599,6 +655,7 @@ Expected responses:
 | `404 Not Found` | No webhook configured for this path. |
 | `413 Payload Too Large` | Body exceeds `max_body_bytes`. |
 | `429 Too Many Requests` | Rate limit exceeded. |
+| `503 triggers paused` | Master [Pause](#pause-and-resume) toggle is active. Includes `Retry-After: 60`. |
 
 ## Troubleshooting
 
diff --git a/docs/tutorials/install.md b/docs/tutorials/install.md
index 773c9bd0..e2cd80d1 100644
--- a/docs/tutorials/install.md
+++ b/docs/tutorials/install.md
@@ -79,6 +79,9 @@ npm install -g @google/gemini-cli
 
 Gemini CLI uses Google AI Studio or Vertex AI for authentication. Run `gemini` and sign in with your Google account. Supports plan mode, sandboxing, and automatic model routing (Pro for planning, Flash for implementation).
 
+!!! tip "Headless trust"
+    Untether runs Gemini with `--skip-trust` by default (v0.35.3+, [#471](https://github.com/littlebearapps/untether/issues/471)) so projects outside `~/.gemini/trustedFolders.json` work in headless mode. Set `[gemini] skip_trust = false` in `untether.toml` if you'd rather enforce Gemini's project-local trust gate.
+
 ### AMP
 
 ```sh
@@ -135,13 +138,13 @@ section and profile picture for your bot, see /help for a
 list of commands.
 
 Use this token to access the HTTP API:
-123456789:ABCdefGHIjklMNOpqrsTUVwxyz
+<BOT_ID>:<BOT_TOKEN>
 
 Keep your token secure and store it safely, it can be used
 by anyone to control your bot.
 ```
 
-Copy the token (the `123456789:ABC...` part).
+Copy the token (the `<BOT_ID>:<BOT_TOKEN>` part).
 
 <!-- TODO: capture screenshot -->
 <!-- <img src="../assets/screenshots/botfather-newbot.jpg" alt="BotFather /newbot flow showing the generated token" width="360" loading="lazy" /> -->
@@ -328,7 +331,7 @@ Untether is now running and listening for messages!
 
 ## What just happened
 
-Your config file lives at `~/.untether/untether.toml`. The exact contents depend on your workflow choice:
+Your config file lives at `~/.untether/untether.toml`. The onboarding wizard populates the required fields including `allowed_user_ids` (your Telegram user ID — required as of v0.35.3, [#377](https://github.com/littlebearapps/untether/issues/377)). The exact contents depend on your workflow choice:
 
 === "assistant"
 
@@ -354,6 +357,7 @@ Your config file lives at `~/.untether/untether.toml`. The exact contents depend
         [transports.telegram]
         bot_token = "..."
         chat_id = 123456789
+        allowed_user_ids = [123456789]  # your Telegram user ID — required (#377)
         session_mode = "chat"       # auto-resume
         show_resume_line = false    # cleaner chat
 
@@ -386,6 +390,7 @@ Your config file lives at `~/.untether/untether.toml`. The exact contents depend
         [transports.telegram]
         bot_token = "..."
         chat_id = -1001234567890    # forum group
+        allowed_user_ids = [123456789, 234567890]  # required (#377) — list each teammate's Telegram user ID
         session_mode = "chat"
         show_resume_line = false
 
@@ -418,6 +423,7 @@ Your config file lives at `~/.untether/untether.toml`. The exact contents depend
         [transports.telegram]
         bot_token = "..."
         chat_id = 123456789
+        allowed_user_ids = [123456789]  # your Telegram user ID — required (#377)
         session_mode = "stateless"  # reply-to-continue
         show_resume_line = true     # always show resume lines
 
diff --git a/llms-full.txt b/llms-full.txt
index 9fbd926c..41730f39 100644
--- a/llms-full.txt
+++ b/llms-full.txt
@@ -438,13 +438,13 @@ section and profile picture for your bot, see /help for a
 list of commands.
 
 Use this token to access the HTTP API:
-123456789:ABCdefGHIjklMNOpqrsTUVwxyz
+<BOT_ID>:<BOT_TOKEN>
 
 Keep your token secure and store it safely, it can be used
 by anyone to control your bot.
 ```
 
-Copy the token (the `123456789:ABC...` part).
+Copy the token (the `<BOT_ID>:<BOT_TOKEN>` part).
 
 !!! warning "Keep your token secret"
     Anyone with your bot token can control your bot. Don't commit it to git or share it publicly.
diff --git a/pyproject.toml b/pyproject.toml
index ddc4a16b..7eee0b28 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -2,7 +2,7 @@
 name = "untether"
 authors = [{name = "Little Bear Apps", email = "hello@littlebearapps.com"}]
 maintainers = [{name = "Little Bear Apps", email = "hello@littlebearapps.com"}]
-version = "0.35.2"
+version = "0.35.3rc13"
 keywords = ["telegram", "claude-code", "codex", "opencode", "pi", "gemini-cli", "amp", "ai-agents", "coding-assistant", "remote-control", "cli-bridge"]
 description = "Run AI coding agents from your phone. Bridges Claude Code, Codex, OpenCode, Pi, Gemini CLI, and Amp to Telegram with interactive permissions, voice input, cost tracking, and live progress."
 readme = {file = "README.md", content-type = "text/markdown"}
@@ -82,7 +82,7 @@ at = "untether.telegram.commands.at:BACKEND"
 health = "untether.telegram.commands.health:BACKEND"
 
 [build-system]
-requires = ["uv_build>=0.9.18,<0.11.0"]
+requires = ["uv_build>=0.9.18,<0.12.0"]
 build-backend = "uv_build"
 
 [dependency-groups]
diff --git a/src/untether/config_migrations.py b/src/untether/config_migrations.py
index b6eb0f52..e060b1ad 100644
--- a/src/untether/config_migrations.py
+++ b/src/untether/config_migrations.py
@@ -41,9 +41,15 @@ def _migrate_legacy_telegram(config: dict[str, Any], *, config_path: Path) -> bo
         telegram["bot_token"] = config["bot_token"]
     if "chat_id" in config and "chat_id" not in telegram:
         telegram["chat_id"] = config["chat_id"]
+    # #377: top-level `allow_any_user` (legacy form) migrates alongside the
+    # other telegram fields so the validator that gates an empty allowlist
+    # doesn't fire on the migrated config.
+    if "allow_any_user" in config and "allow_any_user" not in telegram:
+        telegram["allow_any_user"] = config["allow_any_user"]
 
     config.pop("bot_token", None)
     config.pop("chat_id", None)
+    config.pop("allow_any_user", None)
     config.setdefault("transport", "telegram")
     return True
 
diff --git a/src/untether/cost_tracker.py b/src/untether/cost_tracker.py
index e390c981..fd872cd5 100644
--- a/src/untether/cost_tracker.py
+++ b/src/untether/cost_tracker.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import threading
 import time
 from dataclasses import dataclass
 
@@ -9,8 +10,13 @@
 
 logger = get_logger(__name__)
 
-# Daily cost accumulator: (date_str, total_cost)
+# Daily cost accumulator: (date_str, total_cost).
+# #379: guarded by `_daily_cost_lock` so concurrent finalize_run calls can't
+# race the read-modify-write and silently lose a run's cost. The critical
+# section is a single tuple assignment (sub-microsecond), so a `threading.Lock`
+# is fine — both async tasks (cooperative) and threaded callers are safe.
 _daily_cost: tuple[str, float] = ("", 0.0)
+_daily_cost_lock = threading.Lock()
 
 
 @dataclass(slots=True)
@@ -38,18 +44,21 @@ def record_run_cost(cost: float) -> None:
     """Record the cost of a completed run for daily tracking."""
     global _daily_cost
     today = _today()
-    date, total = _daily_cost
-    _daily_cost = (today, cost) if date != today else (today, total + cost)
+    with _daily_cost_lock:
+        date, total = _daily_cost
+        _daily_cost = (today, cost) if date != today else (today, total + cost)
+        daily_total = _daily_cost[1]
     logger.debug(
         "cost_tracker.recorded",
         cost=cost,
-        daily_total=_daily_cost[1],
+        daily_total=daily_total,
     )
 
 
 def get_daily_cost() -> float:
     """Get today's accumulated cost."""
-    date, total = _daily_cost
+    with _daily_cost_lock:
+        date, total = _daily_cost
     if date != _today():
         return 0.0
     return total
diff --git a/src/untether/logging.py b/src/untether/logging.py
index b4cab9bd..fcff2eba 100644
--- a/src/untether/logging.py
+++ b/src/untether/logging.py
@@ -14,7 +14,11 @@
 
 TELEGRAM_TOKEN_RE = re.compile(r"bot\d+:[A-Za-z0-9_-]+")
 TELEGRAM_BARE_TOKEN_RE = re.compile(r"\b\d+:[A-Za-z0-9_-]{10,}\b")
-# Common API key patterns (OpenAI, GitHub, generic bearer tokens)
+# Common API key patterns (OpenAI, GitHub, generic bearer tokens).
+# #213: sk-proj-... is the project-key variant; underscore/hyphen permitted
+# (so the generic sk- pattern with [A-Za-z0-9] alone misses them). Match
+# project keys first so the generic OPENAI_KEY_RE doesn't partially redact.
+OPENAI_PROJECT_KEY_RE = re.compile(r"\bsk-proj-[A-Za-z0-9_-]{20,}\b")
 OPENAI_KEY_RE = re.compile(r"\bsk-[A-Za-z0-9]{20,}\b")
 GITHUB_TOKEN_RE = re.compile(r"\b(ghp_|ghs_|gho_|github_pat_)[A-Za-z0-9_]{10,}\b")
 
@@ -75,6 +79,7 @@ def _drop_below_level(
 def _redact_text(value: str) -> str:
     redacted = TELEGRAM_TOKEN_RE.sub("bot[REDACTED]", value)
     redacted = TELEGRAM_BARE_TOKEN_RE.sub("[REDACTED_TOKEN]", redacted)
+    redacted = OPENAI_PROJECT_KEY_RE.sub("[REDACTED_KEY]", redacted)
     redacted = OPENAI_KEY_RE.sub("[REDACTED_KEY]", redacted)
     return GITHUB_TOKEN_RE.sub("[REDACTED_TOKEN]", redacted)
 
diff --git a/src/untether/loop_scheduler.py b/src/untether/loop_scheduler.py
new file mode 100644
index 00000000..dc4ed7fb
--- /dev/null
+++ b/src/untether/loop_scheduler.py
@@ -0,0 +1,920 @@
+"""Untether-side scheduler for /loop and ScheduleWakeup (#289).
+
+Claude Code's session-scoped scheduler dies when the ``claude --print``
+subprocess exits — verified empirically against ``claude`` 2.1.129/2.1.132
+in `docs/plans/2026-05-06-289-loop-and-cron-interception.md` (Probe 1).
+This module observes ``CronCreate`` / ``ScheduleWakeup`` / ``CronDelete``
+tool_use events at the JSONL layer (wired in :mod:`untether.runners.claude`),
+captures the user's intent (cron expression + prompt OR delay + prompt),
+and at each fire interval spawns ``claude --resume <session_id>`` with the
+original prompt re-issued as a fresh user turn.
+
+State is persisted to ``active_loops.json`` (sibling to the config file)
+via :func:`untether.utils.json_state.atomic_write_json` so loops survive
+Untether restarts.
+
+Default OFF — opt-in per-chat via ``/config → 🔁 Loop mode``. When the
+toggle is OFF (the default) the observer never reaches this module so
+behaviour matches the pre-#289 baseline.
+"""
+
+from __future__ import annotations
+
+import datetime
+import json
+import secrets
+import time
+from collections import defaultdict
+from collections.abc import Awaitable, Callable
+from dataclasses import dataclass, field, replace
+from pathlib import Path
+from typing import Any, Literal
+
+import anyio
+from anyio.abc import TaskGroup
+
+from .context import RunContext
+from .logging import get_logger
+from .model import EngineId, ResumeToken
+from .transport import ChannelId, RenderedMessage, SendOptions, Transport
+from .triggers.cron import cron_matches
+from .utils.json_state import atomic_write_json
+
+logger = get_logger(__name__)
+
+__all__ = [
+    "STATE_FILENAME",
+    "LoopSchedulerError",
+    "active_count",
+    "bind_upstream_id",
+    "cancel_by_token",
+    "cancel_by_upstream_id",
+    "cancel_pending_for_chat",
+    "install",
+    "is_do_not_resume",
+    "mark_do_not_resume",
+    "next_fire_for_session",
+    "pending_for_chat",
+    "register_pending_cron",
+    "register_pending_wakeup",
+    "uninstall",
+]
+
+STATE_FILENAME = "active_loops.json"
+
+LoopKind = Literal["cron", "wakeup"]
+RunJobFn = Callable[..., Awaitable[None]]
+IsChatBusyFn = Callable[[int], bool]
+
+
+@dataclass(slots=True)
+class _LoopEntry:
+    token: str
+    upstream_cron_id: str | None
+    tool_use_id: str
+    chat_id: int
+    thread_id: int | None
+    kind: LoopKind
+    cron_expression: str | None
+    delay_seconds: float | None
+    recurring: bool
+    prompt: str
+    fallback_first_user_message: str | None
+    fire_at_monotonic: float
+    fire_at_wallclock: float
+    iteration_count: int
+    max_iterations: int
+    max_total_duration_hours: int
+    created_at_wallclock: float
+    expires_at_wallclock: float
+    context: RunContext | None
+    engine_override: EngineId | None
+    resume_token: str
+    # Concurrency: generation increments on every re-arm so older _arm_timer
+    # tasks (still sleeping from a previous round) can detect they are stale
+    # and bail out instead of double-firing.  cancel_event is set when the
+    # entry is cancelled or re-armed so a pending _arm_timer can interrupt
+    # its sleep promptly.
+    generation: int = 0
+    cancel_event: anyio.Event = field(default_factory=anyio.Event)
+    cancelled: bool = False
+    fired: bool = False
+
+
+# Module globals — mirror at_scheduler.py shape so install/uninstall feels
+# the same to readers familiar with that module.
+_TASK_GROUP: TaskGroup | None = None
+_RUN_JOB: RunJobFn | None = None
+_TRANSPORT: Transport | None = None
+_DEFAULT_CHAT_ID: int | None = None
+_STATE_PATH: Path | None = None
+_IS_CHAT_BUSY: IsChatBusyFn | None = None
+
+_PENDING_BY_TOKEN: dict[str, _LoopEntry] = {}
+_PENDING_BY_CHAT: dict[int, set[str]] = defaultdict(set)
+_PENDING_BY_TOOL_USE_ID: dict[str, str] = {}
+_PENDING_BY_UPSTREAM_ID: dict[str, str] = {}
+
+# Sessions that have been cancelled via /cancel — the do-not-resume sentinel
+# (issue #289 design doc §5c).  ``_fire`` refuses to spawn for any session in
+# this set so an upstream session-scoped cron that survives in the JSONL
+# transcript can never be re-fired by us if the user cancels.  Persisted to
+# disk alongside _PENDING entries.
+_DO_NOT_RESUME: set[str] = set()
+
+
+class LoopSchedulerError(Exception):
+    """Raised when scheduling a loop cannot proceed."""
+
+
+def install(
+    task_group: TaskGroup,
+    run_job: RunJobFn,
+    transport: Transport,
+    default_chat_id: int,
+    *,
+    state_path: Path | None = None,
+    is_chat_busy: IsChatBusyFn | None = None,
+) -> None:
+    """Register the task group, ``run_job`` closure, and persistence path.
+
+    Called from :func:`untether.telegram.loop.run_main_loop` once the task
+    group is open and ``run_job`` has been defined.  ``state_path`` should
+    be ``config_path.with_name(STATE_FILENAME)`` so loop state lives next
+    to ``last_update_id.json`` and ``active_progress.json``.  Passing
+    ``None`` disables persistence (used in tests).
+
+    ``is_chat_busy`` is an optional callable used by :func:`_fire` to
+    drop iterations when a previous loop fire (or any other run) is still
+    running for the same chat.  Mirrors upstream's "no catch-up" semantic.
+    """
+    global _TASK_GROUP, _RUN_JOB, _TRANSPORT, _DEFAULT_CHAT_ID
+    global _STATE_PATH, _IS_CHAT_BUSY
+    _TASK_GROUP = task_group
+    _RUN_JOB = run_job
+    _TRANSPORT = transport
+    _DEFAULT_CHAT_ID = int(default_chat_id)
+    _STATE_PATH = state_path
+    _IS_CHAT_BUSY = is_chat_busy
+    if state_path is not None:
+        _restore_from_disk(state_path)
+    logger.info(
+        "loop.installed",
+        default_chat_id=default_chat_id,
+        state_path=str(state_path) if state_path else None,
+        restored=len(_PENDING_BY_TOKEN),
+    )
+
+
+def uninstall() -> None:
+    """Clear installed references — tests and graceful shutdown use this."""
+    global _TASK_GROUP, _RUN_JOB, _TRANSPORT, _DEFAULT_CHAT_ID
+    global _STATE_PATH, _IS_CHAT_BUSY
+    _TASK_GROUP = None
+    _RUN_JOB = None
+    _TRANSPORT = None
+    _DEFAULT_CHAT_ID = None
+    _STATE_PATH = None
+    _IS_CHAT_BUSY = None
+    _PENDING_BY_TOKEN.clear()
+    _PENDING_BY_CHAT.clear()
+    _PENDING_BY_TOOL_USE_ID.clear()
+    _PENDING_BY_UPSTREAM_ID.clear()
+    _DO_NOT_RESUME.clear()
+
+
+# ── Registration ────────────────────────────────────────────────────────
+
+
+def register_pending_cron(
+    *,
+    session_id: str,
+    tool_use_id: str,
+    cron_expression: str,
+    prompt: str,
+    recurring: bool,
+    chat_id: int,
+    thread_id: int | None = None,
+    fallback_first_user_message: str | None = None,
+    context: RunContext | None = None,
+    engine_override: EngineId | None = None,
+    max_iterations: int = 20,
+    max_total_duration_hours: int = 4,
+    expiry_days: int = 7,
+) -> str:
+    """Register a recurring (or one-shot) cron observed in the JSONL stream.
+
+    Returns the Untether-side token (``ut_loop_<8hex>``).  The upstream
+    cron ID arrives later in the matching tool_result and is bound via
+    :func:`bind_upstream_id`.
+    """
+    if _TASK_GROUP is None or _RUN_JOB is None:
+        raise LoopSchedulerError("loop_scheduler not installed")
+    fire_at_monotonic = _next_cron_fire(cron_expression)
+    if fire_at_monotonic is None:
+        raise LoopSchedulerError(f"invalid cron expression: {cron_expression!r}")
+    now_monotonic = time.monotonic()
+    now_wallclock = time.time()
+    fire_at_wallclock = now_wallclock + (fire_at_monotonic - now_monotonic)
+    expires_at = now_wallclock + (expiry_days * 86_400)
+    return _register(
+        kind="cron",
+        session_id=session_id,
+        tool_use_id=tool_use_id,
+        cron_expression=cron_expression,
+        delay_seconds=None,
+        prompt=prompt,
+        recurring=recurring,
+        chat_id=chat_id,
+        thread_id=thread_id,
+        fallback_first_user_message=fallback_first_user_message,
+        context=context,
+        engine_override=engine_override,
+        fire_at_monotonic=fire_at_monotonic,
+        fire_at_wallclock=fire_at_wallclock,
+        expires_at_wallclock=expires_at,
+        max_iterations=max_iterations,
+        max_total_duration_hours=max_total_duration_hours,
+    )
+
+
+def register_pending_wakeup(
+    *,
+    session_id: str,
+    tool_use_id: str,
+    delay_seconds: float,
+    prompt: str,
+    chat_id: int,
+    thread_id: int | None = None,
+    fallback_first_user_message: str | None = None,
+    context: RunContext | None = None,
+    engine_override: EngineId | None = None,
+    max_iterations: int = 20,
+    max_total_duration_hours: int = 4,
+    expiry_days: int = 7,
+) -> str:
+    """Register a one-shot wakeup observed in the JSONL stream.
+
+    ScheduleWakeup is one-shot from the runtime's perspective — Claude
+    self-paces by calling it again from each woken turn.  We treat each
+    observation as a fresh entry with ``recurring=False``.
+    """
+    if _TASK_GROUP is None or _RUN_JOB is None:
+        raise LoopSchedulerError("loop_scheduler not installed")
+    if delay_seconds <= 0:
+        raise LoopSchedulerError(f"delay must be positive, got {delay_seconds!r}")
+    now_monotonic = time.monotonic()
+    now_wallclock = time.time()
+    fire_at_monotonic = now_monotonic + float(delay_seconds)
+    fire_at_wallclock = now_wallclock + float(delay_seconds)
+    expires_at = now_wallclock + (expiry_days * 86_400)
+    return _register(
+        kind="wakeup",
+        session_id=session_id,
+        tool_use_id=tool_use_id,
+        cron_expression=None,
+        delay_seconds=float(delay_seconds),
+        prompt=prompt,
+        recurring=False,
+        chat_id=chat_id,
+        thread_id=thread_id,
+        fallback_first_user_message=fallback_first_user_message,
+        context=context,
+        engine_override=engine_override,
+        fire_at_monotonic=fire_at_monotonic,
+        fire_at_wallclock=fire_at_wallclock,
+        expires_at_wallclock=expires_at,
+        max_iterations=max_iterations,
+        max_total_duration_hours=max_total_duration_hours,
+    )
+
+
+def _register(
+    *,
+    kind: LoopKind,
+    session_id: str,
+    tool_use_id: str,
+    cron_expression: str | None,
+    delay_seconds: float | None,
+    prompt: str,
+    recurring: bool,
+    chat_id: int,
+    thread_id: int | None,
+    fallback_first_user_message: str | None,
+    context: RunContext | None,
+    engine_override: EngineId | None,
+    fire_at_monotonic: float,
+    fire_at_wallclock: float,
+    expires_at_wallclock: float,
+    max_iterations: int,
+    max_total_duration_hours: int,
+) -> str:
+    """Shared body for ``register_pending_cron`` / ``register_pending_wakeup``."""
+    assert _TASK_GROUP is not None  # caller guards
+    token = f"ut_loop_{secrets.token_hex(4)}"
+    trigger_source = f"loop:{token}"
+    if context is None:
+        context = RunContext(trigger_source=trigger_source)
+    else:
+        context = replace(context, trigger_source=trigger_source)
+    entry = _LoopEntry(
+        token=token,
+        upstream_cron_id=None,
+        tool_use_id=tool_use_id,
+        chat_id=chat_id,
+        thread_id=thread_id,
+        kind=kind,
+        cron_expression=cron_expression,
+        delay_seconds=delay_seconds,
+        recurring=recurring,
+        prompt=prompt,
+        fallback_first_user_message=fallback_first_user_message,
+        fire_at_monotonic=fire_at_monotonic,
+        fire_at_wallclock=fire_at_wallclock,
+        iteration_count=0,
+        max_iterations=max_iterations,
+        max_total_duration_hours=max_total_duration_hours,
+        created_at_wallclock=time.time(),
+        expires_at_wallclock=expires_at_wallclock,
+        context=context,
+        engine_override=engine_override,
+        resume_token=session_id,
+    )
+    _PENDING_BY_TOKEN[token] = entry
+    _PENDING_BY_CHAT[chat_id].add(token)
+    _PENDING_BY_TOOL_USE_ID[tool_use_id] = token
+    _persist()
+    _TASK_GROUP.start_soon(_arm_timer, token, entry.generation)
+    logger.info(
+        "loop.scheduled",
+        token=token,
+        kind=kind,
+        chat_id=chat_id,
+        session=session_id,
+        cron_expression=cron_expression,
+        delay_seconds=delay_seconds,
+        recurring=recurring,
+        fire_at_wallclock=fire_at_wallclock,
+    )
+    return token
+
+
+def bind_upstream_id(tool_use_id: str, upstream_id: str) -> None:
+    """Bind the upstream 8-char cron ID to a previously-registered entry.
+
+    Called from the tool_result decode site after parsing the result text
+    via the ``\\bjob ([0-9a-f]{8})\\b`` regex.  No-op if no matching entry
+    (e.g. registration was rejected or the master toggle was off).
+    """
+    token = _PENDING_BY_TOOL_USE_ID.get(tool_use_id)
+    if token is None:
+        return
+    entry = _PENDING_BY_TOKEN.get(token)
+    if entry is None:
+        return
+    entry.upstream_cron_id = upstream_id
+    _PENDING_BY_UPSTREAM_ID[upstream_id] = token
+    _persist()
+
+
+# ── Cancellation ────────────────────────────────────────────────────────
+
+
+def cancel_by_token(token: str) -> bool:
+    """Cancel a single loop by its Untether-side token.  Returns ``True``
+    if a matching pending entry was cancelled, ``False`` otherwise.
+    """
+    entry = _PENDING_BY_TOKEN.get(token)
+    if entry is None or entry.cancelled:
+        return False
+    entry.cancelled = True
+    entry.cancel_event.set()
+    _drop_indexes(entry)
+    _DO_NOT_RESUME.add(entry.resume_token)
+    _persist()
+    logger.info(
+        "loop.cancelled",
+        token=token,
+        chat_id=entry.chat_id,
+        session=entry.resume_token,
+        reason="user_cancel",
+        iterations_completed=entry.iteration_count,
+    )
+    return True
+
+
+def cancel_by_upstream_id(upstream_id: str) -> bool:
+    """Cancel a loop by its upstream 8-char cron ID (CronDelete observed)."""
+    token = _PENDING_BY_UPSTREAM_ID.get(upstream_id)
+    if token is None:
+        return False
+    return cancel_by_token(token)
+
+
+def cancel_pending_for_chat(chat_id: int) -> int:
+    """Cancel all pending loops for ``chat_id``.  Returns count cancelled."""
+    cancelled = 0
+    for token in list(_PENDING_BY_CHAT.get(chat_id, ())):
+        if cancel_by_token(token):
+            cancelled += 1
+    if cancelled:
+        logger.info("loop.cancelled_for_chat", chat_id=chat_id, count=cancelled)
+    return cancelled
+
+
+def _drop_indexes(entry: _LoopEntry) -> None:
+    """Remove an entry from all secondary indexes (idempotent)."""
+    _PENDING_BY_TOKEN.pop(entry.token, None)
+    chat_set = _PENDING_BY_CHAT.get(entry.chat_id)
+    if chat_set is not None:
+        chat_set.discard(entry.token)
+        if not chat_set:
+            _PENDING_BY_CHAT.pop(entry.chat_id, None)
+    _PENDING_BY_TOOL_USE_ID.pop(entry.tool_use_id, None)
+    if entry.upstream_cron_id is not None:
+        _PENDING_BY_UPSTREAM_ID.pop(entry.upstream_cron_id, None)
+
+
+# ── Inspection ──────────────────────────────────────────────────────────
+
+
+def active_count() -> int:
+    """Return the number of pending (non-cancelled, non-fired) loops."""
+    return sum(1 for e in _PENDING_BY_TOKEN.values() if not e.cancelled and not e.fired)
+
+
+def pending_for_chat(chat_id: int) -> list[_LoopEntry]:
+    """Return a snapshot of pending loop entries for ``chat_id``."""
+    tokens = _PENDING_BY_CHAT.get(chat_id, ())
+    return [
+        _PENDING_BY_TOKEN[t]
+        for t in tokens
+        if t in _PENDING_BY_TOKEN and not _PENDING_BY_TOKEN[t].cancelled
+    ]
+
+
+def next_fire_for_session(session_id: str) -> float | None:
+    """Return the soonest ``fire_at_monotonic`` for ``session_id``, or
+    ``None`` if no pending loop targets that session.
+
+    Used by :mod:`untether.markdown` to render an ``⏰ next iter in Xm Ys``
+    footer line after the subprocess has exited.
+    """
+    candidates = [
+        e.fire_at_monotonic
+        for e in _PENDING_BY_TOKEN.values()
+        if e.resume_token == session_id and not e.cancelled
+    ]
+    if not candidates:
+        return None
+    return min(candidates)
+
+
+def is_do_not_resume(session_id: str) -> bool:
+    """Return ``True`` if ``session_id`` has the do-not-resume sentinel set.
+
+    The fire path consults this before spawning a ``--resume`` subprocess
+    so cancelled loops cannot be revived even if the upstream session-scoped
+    cron survives in the JSONL transcript.  ``/continue`` is a separate
+    user-initiated action and does NOT consult this set (handover default).
+    """
+    return session_id in _DO_NOT_RESUME
+
+
+def mark_do_not_resume(session_id: str) -> None:
+    """Mark ``session_id`` as do-not-resume.  Idempotent.  Persisted."""
+    if session_id in _DO_NOT_RESUME:
+        return
+    _DO_NOT_RESUME.add(session_id)
+    _persist()
+
+
+# ── Fire path ───────────────────────────────────────────────────────────
+
+
+async def _arm_timer(token: str, generation: int) -> None:
+    """Sleep until ``entry.fire_at_monotonic`` then call :func:`_fire`.
+
+    ``generation`` lets a stale arm_timer (left over from a previous round
+    after a re-arm) detect it is no longer the live timer and bail out
+    without double-firing.  The sleep is interrupted promptly via
+    ``entry.cancel_event``.
+    """
+    entry = _PENDING_BY_TOKEN.get(token)
+    if entry is None or entry.cancelled or entry.generation != generation:
+        return
+    delay = max(0.0, entry.fire_at_monotonic - time.monotonic())
+    if delay > 0:
+        with anyio.move_on_after(delay):
+            await entry.cancel_event.wait()
+    entry = _PENDING_BY_TOKEN.get(token)
+    if entry is None or entry.cancelled or entry.generation != generation:
+        return
+    await _fire(token)
+
+
+async def _fire(token: str) -> None:
+    """Fire one iteration of the loop identified by ``token``.
+
+    Sequence:
+    1. Validate entry still pending (not cancelled, not over caps).
+    2. Drop-on-busy: if another run is in flight for our chat, log and
+       skip.  Mirrors upstream's "no catch-up" semantic.
+    3. Race avoidance: if the originating subprocess is still alive, sleep
+       ``redundancy_check_interval`` and re-arm.
+    4. Honour the do-not-resume sentinel.
+    5. Spawn the iteration via :func:`_spawn_loop_iteration`.
+    6. Re-arm next fire (recurring) or expire (one-shot).
+    """
+    entry = _PENDING_BY_TOKEN.get(token)
+    if entry is None or entry.cancelled:
+        return
+    now_wallclock = time.time()
+    if now_wallclock >= entry.expires_at_wallclock:
+        _expire(entry, reason="expired_7d")
+        return
+    if entry.iteration_count >= entry.max_iterations:
+        _expire(entry, reason="max_iterations")
+        return
+    if (
+        now_wallclock - entry.created_at_wallclock
+        >= entry.max_total_duration_hours * 3600
+    ):
+        _expire(entry, reason="max_total_duration")
+        return
+    if is_do_not_resume(entry.resume_token):
+        _expire(entry, reason="do_not_resume")
+        return
+    if _IS_CHAT_BUSY is not None and _IS_CHAT_BUSY(entry.chat_id):
+        logger.warning(
+            "loop.iteration_skipped_previous_running",
+            token=token,
+            chat_id=entry.chat_id,
+            iteration=entry.iteration_count + 1,
+        )
+        # Still re-arm — we want to try the next interval.
+        _rearm_or_expire(entry)
+        return
+    # Race avoidance — skip if the originating subprocess is still alive
+    # (control_request awaiting Telegram input, or any other reason).
+    if _is_session_alive_safe(entry.resume_token):
+        logger.info(
+            "loop.fire_skipped_subprocess_alive",
+            token=token,
+            session=entry.resume_token,
+        )
+        await _redundancy_sleep_then_retry(token)
+        return
+    await _spawn_loop_iteration(entry)
+    _rearm_or_expire(entry)
+
+
+async def _spawn_loop_iteration(entry: _LoopEntry) -> None:
+    """Send the notification and dispatch the run via ``_RUN_JOB``."""
+    if entry.cancelled:
+        return
+    assert _RUN_JOB is not None and _TRANSPORT is not None
+    iteration = entry.iteration_count + 1
+    label = f"\N{ALARM CLOCK} /loop · iter {iteration}/{entry.max_iterations}"
+    try:
+        notify_ref = await _TRANSPORT.send(
+            channel_id=_as_channel_id(entry.chat_id),
+            message=RenderedMessage(text=label),
+            options=SendOptions(notify=False),
+        )
+    except Exception as exc:  # noqa: BLE001
+        logger.error(
+            "loop.notify_failed",
+            token=entry.token,
+            chat_id=entry.chat_id,
+            error=str(exc),
+            error_type=exc.__class__.__name__,
+        )
+        return
+    if notify_ref is None:
+        logger.error("loop.notify_failed", token=entry.token, chat_id=entry.chat_id)
+        return
+    fire_prompt = entry.prompt
+    if fire_prompt == "<<autonomous-loop-dynamic>>":
+        fire_prompt = entry.fallback_first_user_message or fire_prompt
+    wrapped = (
+        f"Loop iteration {iteration}: {fire_prompt}. "
+        "Do the task now; do not summarize old results unless necessary."
+    )
+    logger.info(
+        "loop.firing",
+        token=entry.token,
+        iteration=iteration,
+        session=entry.resume_token,
+        kind=entry.kind,
+    )
+    try:
+        await _RUN_JOB(
+            entry.chat_id,
+            notify_ref.message_id,
+            wrapped,
+            ResumeToken(engine="claude", value=entry.resume_token),
+            entry.context,
+            entry.thread_id,
+            None,  # chat_session_key
+            None,  # reply_ref
+            None,  # on_thread_known
+            entry.engine_override,
+            None,  # progress_ref
+        )
+    except Exception as exc:  # noqa: BLE001
+        logger.warning(
+            "loop.fired_failed",
+            token=entry.token,
+            iteration=iteration,
+            error=str(exc),
+            error_type=exc.__class__.__name__,
+        )
+        return
+    entry.iteration_count = iteration
+    logger.info(
+        "loop.fired_ok",
+        token=entry.token,
+        iteration=iteration,
+        session=entry.resume_token,
+    )
+
+
+def _rearm_or_expire(entry: _LoopEntry) -> None:
+    """After a fire (or busy-skip), re-arm the timer or expire the loop."""
+    if entry.cancelled:
+        return
+    if not entry.recurring:
+        _expire(entry, reason="one_shot_complete")
+        return
+    if entry.iteration_count >= entry.max_iterations:
+        _expire(entry, reason="max_iterations")
+        return
+    if entry.kind == "cron" and entry.cron_expression is not None:
+        next_fire = _next_cron_fire(entry.cron_expression)
+        if next_fire is None:
+            _expire(entry, reason="cron_unparseable")
+            return
+        entry.fire_at_monotonic = next_fire
+        entry.fire_at_wallclock = time.time() + (next_fire - time.monotonic())
+    elif entry.delay_seconds is not None:
+        entry.fire_at_monotonic = time.monotonic() + entry.delay_seconds
+        entry.fire_at_wallclock = time.time() + entry.delay_seconds
+    # Bump generation so any stale _arm_timer task from the previous round
+    # bails out instead of double-firing.  Reset cancel_event for the new
+    # round so the fresh _arm_timer starts unset.
+    entry.generation += 1
+    entry.cancel_event = anyio.Event()
+    _persist()
+    if _TASK_GROUP is not None:
+        _TASK_GROUP.start_soon(_arm_timer, entry.token, entry.generation)
+
+
+async def _redundancy_sleep_then_retry(token: str) -> None:
+    """Sleep redundancy_check_interval then re-fire.  Bounded to avoid
+    runaway spinning if the subprocess never exits."""
+    interval = _redundancy_check_interval()
+    await anyio.sleep(interval)
+    if _TASK_GROUP is not None:
+        _TASK_GROUP.start_soon(_fire, token)
+
+
+def _expire(entry: _LoopEntry, *, reason: str) -> None:
+    """Mark an entry as fired/cancelled and drop from indexes.  Logs once."""
+    if entry.cancelled and reason != "do_not_resume":
+        return
+    entry.cancelled = True
+    entry.cancel_event.set()
+    _drop_indexes(entry)
+    _persist()
+    logger.info(
+        "loop.expired",
+        token=entry.token,
+        chat_id=entry.chat_id,
+        session=entry.resume_token,
+        reason=reason,
+        iterations_completed=entry.iteration_count,
+    )
+
+
+def _is_session_alive_safe(session_id: str) -> bool:
+    """Lazy import of :func:`untether.runners.claude.is_session_alive`.
+
+    Lazy because the runner module imports back into this module at observer
+    wiring time (Commit B in the #289 plan).
+    """
+    try:
+        from .runners.claude import is_session_alive
+    except ImportError:
+        return False
+    return is_session_alive(session_id)
+
+
+def _redundancy_check_interval() -> int:
+    """Read the configured redundancy check interval, with a safe fallback."""
+    try:
+        from .settings import load_settings_if_exists
+
+        result = load_settings_if_exists()
+        if result is None:
+            return 30
+        settings, _ = result
+        return int(settings.loop.redundancy_check_interval)
+    except Exception:  # noqa: BLE001
+        return 30
+
+
+def _next_cron_fire(expression: str) -> float | None:
+    """Compute the next monotonic-clock instant matching ``expression``.
+
+    Walks one minute at a time from ``now + 60s`` (to avoid double-firing
+    the current minute) up to a 366-day horizon.  Returns ``None`` if the
+    expression never matches in that window (almost certainly malformed).
+    """
+    if not expression or not expression.strip():
+        return None
+    fields = expression.strip().split()
+    if len(fields) != 5:
+        return None
+    now_monotonic = time.monotonic()
+    now_wallclock_dt = datetime.datetime.now().replace(second=0, microsecond=0)
+    horizon_minutes = 366 * 24 * 60
+    for i in range(1, horizon_minutes + 1):
+        candidate = now_wallclock_dt + datetime.timedelta(minutes=i)
+        try:
+            if cron_matches(expression, candidate):
+                offset_seconds = (candidate - datetime.datetime.now()).total_seconds()
+                return now_monotonic + max(0.0, offset_seconds)
+        except Exception:  # noqa: BLE001
+            return None
+    return None
+
+
+def _as_channel_id(chat_id: int) -> ChannelId:
+    return chat_id
+
+
+# ── Persistence ─────────────────────────────────────────────────────────
+
+
+def _persist() -> None:
+    """Write the current pending entries + do-not-resume sentinel to disk.
+
+    No-op if persistence is disabled (``_STATE_PATH is None``).  Errors are
+    logged and swallowed — losing persistence is preferable to crashing the
+    bot loop.
+    """
+    if _STATE_PATH is None:
+        return
+    payload: dict[str, Any] = {
+        "schema_version": 1,
+        "entries": [_serialize_entry(e) for e in _PENDING_BY_TOKEN.values()],
+        "do_not_resume": sorted(_DO_NOT_RESUME),
+    }
+    try:
+        atomic_write_json(_STATE_PATH, payload)
+    except (OSError, ValueError) as exc:
+        logger.warning(
+            "loop.persist_failed",
+            path=str(_STATE_PATH),
+            error=str(exc),
+            error_type=exc.__class__.__name__,
+        )
+
+
+def _serialize_entry(entry: _LoopEntry) -> dict[str, Any]:
+    """Serialize a ``_LoopEntry`` for JSON persistence.
+
+    ``cancel_event`` and ``generation`` are dropped (re-created on load).
+    ``context`` is serialized via its dataclass fields so we can restore
+    the project mapping on reload.
+    """
+    ctx = entry.context
+    return {
+        "token": entry.token,
+        "upstream_cron_id": entry.upstream_cron_id,
+        "tool_use_id": entry.tool_use_id,
+        "chat_id": entry.chat_id,
+        "thread_id": entry.thread_id,
+        "kind": entry.kind,
+        "cron_expression": entry.cron_expression,
+        "delay_seconds": entry.delay_seconds,
+        "recurring": entry.recurring,
+        "prompt": entry.prompt,
+        "fallback_first_user_message": entry.fallback_first_user_message,
+        "fire_at_wallclock": entry.fire_at_wallclock,
+        "iteration_count": entry.iteration_count,
+        "max_iterations": entry.max_iterations,
+        "max_total_duration_hours": entry.max_total_duration_hours,
+        "created_at_wallclock": entry.created_at_wallclock,
+        "expires_at_wallclock": entry.expires_at_wallclock,
+        "context_project": ctx.project if ctx is not None else None,
+        "context_branch": ctx.branch if ctx is not None else None,
+        "context_permission_mode": ctx.permission_mode if ctx is not None else None,
+        "engine_override": entry.engine_override,
+        "resume_token": entry.resume_token,
+        "cancelled": entry.cancelled,
+    }
+
+
+def _deserialize_entry(data: dict[str, Any]) -> _LoopEntry | None:
+    """Inverse of ``_serialize_entry``.  Returns ``None`` if the payload is
+    invalid.  Re-creates the cancel ``Event`` and recomputes
+    ``fire_at_monotonic`` from the persisted wall-clock time (or zero if
+    past)."""
+    try:
+        now_wallclock = time.time()
+        now_monotonic = time.monotonic()
+        fire_at_wallclock = float(data["fire_at_wallclock"])
+        offset = max(0.0, fire_at_wallclock - now_wallclock)
+        fire_at_monotonic = now_monotonic + offset
+        token = str(data["token"])
+        ctx = RunContext(
+            project=data.get("context_project"),
+            branch=data.get("context_branch"),
+            trigger_source=f"loop:{token}",
+            permission_mode=data.get("context_permission_mode"),
+        )
+        return _LoopEntry(
+            token=token,
+            upstream_cron_id=data.get("upstream_cron_id"),
+            tool_use_id=str(data["tool_use_id"]),
+            chat_id=int(data["chat_id"]),
+            thread_id=data.get("thread_id"),
+            kind=data["kind"],
+            cron_expression=data.get("cron_expression"),
+            delay_seconds=(
+                float(data["delay_seconds"])
+                if data.get("delay_seconds") is not None
+                else None
+            ),
+            recurring=bool(data["recurring"]),
+            prompt=str(data["prompt"]),
+            fallback_first_user_message=data.get("fallback_first_user_message"),
+            fire_at_monotonic=fire_at_monotonic,
+            fire_at_wallclock=fire_at_wallclock,
+            iteration_count=int(data.get("iteration_count", 0)),
+            max_iterations=int(data.get("max_iterations", 20)),
+            max_total_duration_hours=int(data.get("max_total_duration_hours", 4)),
+            created_at_wallclock=float(data.get("created_at_wallclock", now_wallclock)),
+            expires_at_wallclock=float(
+                data.get("expires_at_wallclock", now_wallclock + 7 * 86_400)
+            ),
+            context=ctx,
+            engine_override=data.get("engine_override"),
+            resume_token=str(data["resume_token"]),
+            cancelled=bool(data.get("cancelled", False)),
+        )
+    except (KeyError, TypeError, ValueError) as exc:
+        logger.warning(
+            "loop.restore.entry_invalid",
+            error=str(exc),
+            error_type=exc.__class__.__name__,
+        )
+        return None
+
+
+def _restore_from_disk(path: Path) -> None:
+    """Read ``path`` and re-arm timers for non-cancelled entries.
+
+    Past ``fire_at_wallclock`` values fire immediately (no catch-up
+    multiplier) — mirrors upstream's "no catch-up" semantic.  Cancelled
+    entries and the do-not-resume sentinel are preserved.
+    """
+    if not path.exists():
+        return
+    try:
+        raw = json.loads(path.read_text(encoding="utf-8"))
+    except (OSError, ValueError) as exc:
+        logger.warning(
+            "loop.restore.read_failed",
+            path=str(path),
+            error=str(exc),
+            error_type=exc.__class__.__name__,
+        )
+        return
+    if not isinstance(raw, dict):
+        return
+    do_not_resume = raw.get("do_not_resume", [])
+    if isinstance(do_not_resume, list):
+        _DO_NOT_RESUME.update(str(s) for s in do_not_resume)
+    entries = raw.get("entries", [])
+    if not isinstance(entries, list):
+        return
+    restored = 0
+    for raw_entry in entries:
+        if not isinstance(raw_entry, dict):
+            continue
+        entry = _deserialize_entry(raw_entry)
+        if entry is None or entry.cancelled:
+            continue
+        _PENDING_BY_TOKEN[entry.token] = entry
+        _PENDING_BY_CHAT[entry.chat_id].add(entry.token)
+        _PENDING_BY_TOOL_USE_ID[entry.tool_use_id] = entry.token
+        if entry.upstream_cron_id is not None:
+            _PENDING_BY_UPSTREAM_ID[entry.upstream_cron_id] = entry.token
+        if _TASK_GROUP is not None:
+            _TASK_GROUP.start_soon(_arm_timer, entry.token, entry.generation)
+        restored += 1
+    if restored:
+        logger.info("loop.restored", path=str(path), count=restored)
diff --git a/src/untether/markdown.py b/src/untether/markdown.py
index 65527352..7617a424 100644
--- a/src/untether/markdown.py
+++ b/src/untether/markdown.py
@@ -157,16 +157,64 @@ def format_action_title(action: Action, *, command_width: int | None) -> str:
     return shorten(title, command_width)
 
 
+def format_duration(seconds: float | int) -> str:
+    """Render a duration as ``Nm Ys`` (≥60s) or ``Ys``.
+
+    Used by the #481 long-running-action tail to surface elapsed time
+    on the progress message even when no JSONL events are arriving.
+    Negative values render as ``0s`` (defensive — clock skew shouldn't
+    break the renderer).
+    """
+    s = max(0, int(seconds))
+    if s < 60:
+        return f"{s}s"
+    minutes, secs = divmod(s, 60)
+    return f"{minutes}m {secs:02d}s"
+
+
+def format_countdown(seconds: float | int) -> str:
+    """Render a remaining-time countdown — alias of format_duration.
+
+    Kept distinct so call sites read clearly (countdown vs elapsed) and
+    so future formatting differences (e.g. ``ETA 14:32``) can land in
+    one place.
+    """
+    return format_duration(seconds)
+
+
 def format_action_line(
     action: Action,
     phase: str,
     ok: bool | None,
     *,
     command_width: int | None,
+    elapsed_seconds: float | None = None,
 ) -> str:
+    """Render one action line for the progress message.
+
+    #481: ``elapsed_seconds`` triggers the long-running tail. When the
+    action is non-completed AND age > 60 s, append ``· <elapsed> · <key arg>``
+    so a glancing user can answer "is it alive? what is it doing? for how
+    long?" without waiting for the next JSONL event. The tail fires
+    regardless of formatter verbosity — verbose mode keeps its existing
+    ``→ <detail>`` second line below (slight redundancy is fine; verbose
+    users opted in).
+    """
     if phase != "completed":
         status = STATUS["update"] if phase == "updated" else STATUS["running"]
-        return f"{status} {format_action_title(action, command_width=command_width)}"
+        line = f"{status} {format_action_title(action, command_width=command_width)}"
+        if elapsed_seconds is not None and elapsed_seconds > 60:
+            elapsed_str = format_duration(elapsed_seconds)
+            detail = format_verbose_detail(action)
+            if detail:
+                # Strip the ``→ `` prefix so the tail reads as
+                # ``▸ Bash · 3m 47s · npm run build`` rather than
+                # ``▸ Bash · 3m 47s · → npm run build``.
+                detail_clean = detail.lstrip("→ ").strip()
+                line += f" · {elapsed_str} · {shorten(detail_clean, 80)}"
+            else:
+                line += f" · {elapsed_str}"
+        return line
     status = action_status(action, completed=True, ok=ok)
     suffix = action_suffix(action)
     return (
@@ -245,6 +293,59 @@ def format_verbose_detail(action: Action) -> str | None:
             return f'→ "{shorten(query, 80)}"'
         return None
 
+    # #481: BashOutput — Claude Code's mechanism for polling backgrounded
+    # Bash shells. The previous tool_result_event populated
+    # ``detail["result_preview"]`` with the recent stdout snapshot; render
+    # the LAST line as the verbose detail so users see live polling output
+    # (e.g. ``→ Deploy Production: in_progress``) instead of a generic
+    # ``▸ BashOutput`` line for 10+ minutes.
+    if name == "BashOutput":
+        preview = detail.get("result_preview") or ""
+        if isinstance(preview, str) and preview.strip():
+            last = preview.rstrip().splitlines()[-1]
+            if last:
+                return f"→ {shorten(last, 120)}"
+        bash_id = inp.get("bash_id", "")
+        if isinstance(bash_id, str) and bash_id:
+            return f"→ bash:{bash_id[-8:]}"
+        return None
+
+    # #481: KillShell — show which background bash is being terminated.
+    if name == "KillShell":
+        bash_id = inp.get("shell_id") or inp.get("bash_id") or ""
+        if isinstance(bash_id, str) and bash_id:
+            return f"→ kill bash:{bash_id[-8:]}"
+        return None
+
+    # #481: ScheduleWakeup — render countdown from heartbeat-mutated
+    # ``detail['countdown_s']`` (set by ProgressEdits._heartbeat_tick), or
+    # fall back to ``delaySeconds`` from input. Optional ``reason`` field
+    # is shown in quotes when present.
+    if name == "ScheduleWakeup":
+        reason = inp.get("reason")
+        countdown_s = detail.get("countdown_s")
+        if countdown_s is None:
+            delay = (
+                inp.get("delaySeconds")
+                or (inp.get("delay_ms") or 0) / 1000.0
+                or (inp.get("timeout_ms") or 0) / 1000.0
+            )
+            if delay > 0:
+                countdown_s = float(delay)
+        if countdown_s is None or countdown_s < 0:
+            return None
+        timer = format_countdown(countdown_s)
+        if isinstance(reason, str) and reason.strip():
+            return f'→ fires in {timer} · "{shorten(reason, 60)}"'
+        return f"→ fires in {timer}"
+
+    # #481: Monitor — render countdown from heartbeat-mutated countdown_s.
+    if name == "Monitor":
+        countdown_s = detail.get("countdown_s")
+        if isinstance(countdown_s, (int, float)) and countdown_s > 0:
+            return f"→ monitoring · {format_countdown(countdown_s)} remaining"
+        return None
+
     # MCP tools: show server:tool
     server = detail.get("server", "")
     tool = detail.get("tool", name)
@@ -325,6 +426,12 @@ def format_meta_line(meta: dict[str, Any]) -> str | None:
     trigger = meta.get("trigger")
     if isinstance(trigger, str) and trigger:
         parts.append(trigger)
+    # #333: show "✓ turn complete" hint on bidirectional Claude sessions
+    # so the user knows the turn is done and the bot is waiting (rather
+    # than processing). Set by translate_claude_event on result.
+    complete = meta.get("complete")
+    if isinstance(complete, str) and complete:
+        parts.append(complete)
     return HEADER_SEP.join(parts) if parts else None
 
 
@@ -340,12 +447,30 @@ def __init__(
         self.command_width = command_width
         self.verbosity = verbosity
 
+    def refresh_from(self, progress: Any) -> None:
+        """Update mutable formatting knobs from a ``ProgressSettings`` snapshot (#269).
+
+        Used by the runner bridge at the start of each run so edits to
+        ``[progress].max_actions`` / ``[progress].verbosity`` in
+        ``untether.toml`` apply on the next run without restarting the bot.
+        Per-chat ``/verbose`` overrides still take precedence — they're
+        rebuilt by ``runner_bridge._resolve_presenter`` from the refreshed
+        defaults each call.
+        """
+        max_actions = getattr(progress, "max_actions", None)
+        if isinstance(max_actions, int):
+            self.max_actions = max(0, max_actions)
+        verbosity = getattr(progress, "verbosity", None)
+        if verbosity in ("compact", "verbose"):
+            self.verbosity = verbosity
+
     def render_progress_parts(
         self,
         state: ProgressState,
         *,
         elapsed_s: float,
         label: str = "working",
+        now: float | None = None,
     ) -> MarkdownParts:
         step = state.action_count or None
         header = format_header(
@@ -354,7 +479,7 @@ def render_progress_parts(
             label=label,
             engine=state.engine,
         )
-        body = self._assemble_body(self._format_actions(state))
+        body = self._assemble_body(self._format_actions(state, now=now))
         return MarkdownParts(
             header=header, body=body, footer=self._format_footer(state)
         )
@@ -397,16 +522,26 @@ def _format_footer(self, state: ProgressState) -> str | None:
             return None
         return HARD_BREAK.join(lines)
 
-    def _format_actions(self, state: ProgressState) -> list[str]:
+    def _format_actions(
+        self, state: ProgressState, *, now: float | None = None
+    ) -> list[str]:
         actions = list(state.actions)
         actions = [] if self.max_actions == 0 else actions[-self.max_actions :]
         lines: list[str] = []
         for action_state in actions:
+            # #481: derive per-action elapsed when both ``now`` and
+            # ``started_at`` are available. Tests that don't pass a clock
+            # default to None → no tail (preserves the existing compact
+            # output for fast actions and unit tests).
+            elapsed_seconds: float | None = None
+            if now is not None and action_state.started_at > 0:
+                elapsed_seconds = max(0.0, now - action_state.started_at)
             line = format_action_line(
                 action_state.action,
                 action_state.display_phase,
                 action_state.ok,
                 command_width=self.command_width,
+                elapsed_seconds=elapsed_seconds,
             )
             lines.append(line)
             if self.verbosity == "verbose":
@@ -432,9 +567,10 @@ def render_progress(
         *,
         elapsed_s: float,
         label: str = "working",
+        now: float | None = None,
     ) -> RenderedMessage:
         parts = self._formatter.render_progress_parts(
-            state, elapsed_s=elapsed_s, label=label
+            state, elapsed_s=elapsed_s, label=label, now=now
         )
         return RenderedMessage(text=assemble_markdown_parts(parts))
 
diff --git a/src/untether/presenter.py b/src/untether/presenter.py
index cc8c29e0..dba3bb08 100644
--- a/src/untether/presenter.py
+++ b/src/untether/presenter.py
@@ -13,6 +13,7 @@ def render_progress(
         *,
         elapsed_s: float,
         label: str = "working",
+        now: float | None = None,
     ) -> RenderedMessage: ...
 
     def render_final(
diff --git a/src/untether/progress.py b/src/untether/progress.py
index ae6ced5b..7a541e70 100644
--- a/src/untether/progress.py
+++ b/src/untether/progress.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import time
 from collections.abc import Callable
 from dataclasses import dataclass
 from typing import Any
@@ -16,6 +17,13 @@ class ActionState:
     completed: bool
     first_seen: int
     last_update: int
+    # #481: wall-clock timestamps for elapsed-time rendering and
+    # heartbeat-driven "action older than 60s" suppression checks.
+    # 0.0 = unset (backward-compat for tests that build ActionState
+    # without a clock). Populated by ProgressTracker.note_event when a
+    # clock callable is configured.
+    started_at: float = 0.0
+    last_update_at: float = 0.0
 
 
 @dataclass(frozen=True, slots=True)
@@ -30,8 +38,18 @@ class ProgressState:
 
 
 class ProgressTracker:
-    def __init__(self, *, engine: str) -> None:
+    def __init__(
+        self,
+        *,
+        engine: str,
+        clock: Callable[[], float] | None = None,
+    ) -> None:
         self.engine = engine
+        # #481: clock callable for ActionState wall-clock timestamps.
+        # Defaults to time.monotonic so production callers don't need to
+        # plumb anything new. Tests can pass a fake clock for deterministic
+        # elapsed-time assertions.
+        self._clock: Callable[[], float] = clock or time.monotonic
         self.resume: ResumeToken | None = None
         self.meta: dict[str, Any] | None = None
         self.action_count = 0
@@ -65,12 +83,15 @@ def note_event(self, event: UntetherEvent) -> bool:
 
                 self._seq += 1
                 seq = self._seq
+                now = self._clock()
 
                 if existing is None:
                     self.action_count += 1
                     first_seen = seq
+                    started_at = now
                 else:
                     first_seen = existing.first_seen
+                    started_at = existing.started_at or now
                 self._actions[action_id] = ActionState(
                     action=action,
                     phase=phase,
@@ -79,6 +100,8 @@ def note_event(self, event: UntetherEvent) -> bool:
                     completed=completed,
                     first_seen=first_seen,
                     last_update=seq,
+                    started_at=started_at,
+                    last_update_at=now,
                 )
                 return True
             case _:
diff --git a/src/untether/runner.py b/src/untether/runner.py
index 40575ed9..a8a2936b 100644
--- a/src/untether/runner.py
+++ b/src/untether/runner.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import contextlib
 import json
 import re
 import signal
@@ -108,9 +109,30 @@ def _rc_label(rc: int) -> str:
     return f"rc={rc}"
 
 
-_ABS_PATH_RE = re.compile(r"(/[\w./-]{3,}/[\w.-]+)")
 _URL_RE = re.compile(r"https?://[^\s\"'<>]+")
 
+# #208: ordered list of absolute-path patterns. More specific roots first so
+# they're not partially eaten by the generic fallback. Stop chars exclude `:`
+# so `path:line` stack-trace markers survive sanitisation.
+_PATH_STOP = r"[^\s'\"<>:]"
+_PATH_PATTERNS = [
+    re.compile(rf"/home/{_PATH_STOP}+"),
+    re.compile(rf"/Users/{_PATH_STOP}+"),
+    re.compile(rf"/root/{_PATH_STOP}*"),
+    re.compile(rf"/private/var/{_PATH_STOP}+"),
+    re.compile(rf"/var/{_PATH_STOP}+"),
+    # The /tmp/ literal is part of a regex used to redact paths from stderr,
+    # not a hardcoded temp directory write — bandit B108 false positive.
+    re.compile(rf"/tmp/{_PATH_STOP}+"),  # nosec B108
+    re.compile(rf"/opt/{_PATH_STOP}+"),
+    re.compile(rf"/srv/{_PATH_STOP}+"),
+    re.compile(rf"/etc/{_PATH_STOP}+"),
+    re.compile(rf"/usr/local/{_PATH_STOP}+"),
+    re.compile(rf"/app/{_PATH_STOP}+"),
+    re.compile(rf"/workspace/{_PATH_STOP}+"),
+    re.compile(r"(/[\w./-]{3,}/[\w.-]+)"),
+]
+
 
 _TOOL_RESULT_EVENT_KIND = "tool_result"
 _ASSISTANT_EVENT_KIND = "assistant"
@@ -194,7 +216,8 @@ def _classify_jsonl_event(raw: Any) -> str:
 
 def _sanitise_stderr(text: str) -> str:
     """Redact absolute paths and URLs from stderr before exposing to users."""
-    text = _ABS_PATH_RE.sub("[path]", text)
+    for pattern in _PATH_PATTERNS:
+        text = pattern.sub("[path]", text)
     text = _URL_RE.sub("[url]", text)
     return text
 
@@ -848,6 +871,15 @@ async def _iter_jsonl_events(
                 pid=pid,
             ):
                 yield evt
+            # #505 After CompletedEvent, stop reading stdout. Otherwise a
+            # child process inheriting the stdout fd (e.g. MCP server,
+            # backgrounded shell) keeps the pipe open and we block on
+            # iter_json_lines waiting for an EOF that never comes.
+            # Audited 2026-05-10 across codex/opencode/pi/gemini/amp:
+            # each engine emits exactly one terminal event, no
+            # post-completion events. Mirrors Claude's override.
+            if stream.did_emit_completed:
+                break
 
     _WATCHDOG_GRACE_SECONDS: float = 5.0
 
@@ -1057,10 +1089,16 @@ async def run_impl(
             "runner.start",
             engine=self.engine,
             resume=resume.value if resume else None,
-            prompt=prompt[:100] + "…" if len(prompt) > 100 else prompt,
             prompt_len=len(prompt),
             args=cmd[1:],
         )
+        # #205: prompt content may carry credentials/PII; keep at DEBUG so it
+        # only surfaces with explicit operator opt-in.
+        logger.debug(
+            "runner.start_prompt",
+            engine=self.engine,
+            prompt_preview=prompt[:100] + "…" if len(prompt) > 100 else prompt,
+        )
 
         # #350 pre-spawn RAM guard — refuse or warn when the host is
         # near-OOM. Runs BEFORE manage_subprocess so a blocked spawn costs
@@ -1138,6 +1176,13 @@ async def run_impl(
                 ):
                     yield evt
                 reader_done.set()
+                # #502 — Close our read end of stderr so drain_stderr
+                # exits even when a child (e.g. an MCP server) inherited
+                # the stderr fd and is keeping it open. Without this the
+                # task group blocks forever waiting on drain_stderr and
+                # `proc.wait()` below is never reached.
+                with contextlib.suppress(Exception):
+                    await proc.stderr.aclose()
 
             rc = await proc.wait()
             stream.proc_returncode = rc
diff --git a/src/untether/runner_bridge.py b/src/untether/runner_bridge.py
index c0893f2c..3b2244f4 100644
--- a/src/untether/runner_bridge.py
+++ b/src/untether/runner_bridge.py
@@ -203,6 +203,28 @@ def _load_watchdog_settings():
         return None
 
 
+def _load_progress_settings():
+    """Load progress settings from config, returning defaults if unavailable.
+
+    Read fresh per-run by ``handle_message`` so edits to ``[progress]`` in
+    ``untether.toml`` apply on the next run without restarting the bot
+    (#269). Sibling of ``_load_footer_settings`` / ``_load_watchdog_settings``.
+    """
+    from .settings import ProgressSettings
+
+    try:
+        from .settings import load_settings_if_exists
+
+        result = load_settings_if_exists()
+        if result is None:
+            return ProgressSettings()
+        settings, _ = result
+        return settings.progress
+    except Exception:  # noqa: BLE001
+        logger.warning("progress_settings.load_failed", exc_info=True)
+        return ProgressSettings()
+
+
 def _load_auto_continue_settings():
     """Load auto-continue settings from config, returning defaults if unavailable."""
     try:
@@ -276,14 +298,29 @@ def _should_auto_continue(
     "- If hooks fire at session end, your final response MUST still contain the "
     "user's requested content. Hook concerns are secondary — briefly note them "
     "AFTER the main content, never instead of it.\n\n"
-    "Every response that completes work MUST end with a structured summary:\n"
+    "Plan-mode requirements (when you call `ExitPlanMode`):\n"
+    "- Your `plan` parameter MUST be a concise 3–5 bullet summary of your "
+    "findings, decisions, or proposed changes — never just a file path. "
+    "Keep it short: the plan is shown to the user for approval, not as the "
+    "final deliverable.\n"
+    "- After `ExitPlanMode` is approved, your next assistant message — "
+    "which becomes the user's final Telegram message — should be a brief "
+    "CLI-style summary: 3–7 bullets or 1–2 short paragraphs covering key "
+    "findings, recommendations, decisions made, and next steps. Aim for "
+    "~500–1500 characters total. Do NOT re-paste the full plan content — "
+    "the user has already seen it during approval. Brevity is the goal; "
+    'do not just write "Plan approved" either.\n\n'
+    "Every response that completes work MUST end with a structured summary "
+    "(keep each section brief — headline bullets, not full content; aim "
+    "for ~500–1500 characters total across the whole summary):\n"
     "  ## Summary\n"
     "  ### Completed\n"
-    "  - [What was done, with specific file paths and line numbers where relevant]\n"
-    "  - [Key decisions made and why]\n"
+    "  - [What was done — short bullets with file paths/line numbers]\n"
+    "  - [Key decisions made and why — one line each]\n"
     "  ### Plan/Document Created (if applicable)\n"
-    "  - [Path and concise summary of any plan, design doc, or document created — "
-    "the user cannot easily open files from Telegram]\n"
+    "  - [Path AND a 3–5 bullet headline summary — the user has already "
+    "seen the plan during approval, so this is a pointer + headline, not "
+    "a re-paste of the full content]\n"
     "  ### Files for Review (if applicable)\n"
     "  - To send files to the user, write them to `.untether-outbox/`\n"
     "  - Example: `mkdir -p .untether-outbox && cp docs/plan.md .untether-outbox/`\n"
@@ -388,18 +425,40 @@ def _resolve_presenter(
     return default_presenter
 
 
+# #410: schema-mismatch surfacing — promoted from one-shot per-process to
+# per-call counter so the issue-watcher actually creates an issue when API-
+# shape drift starts happening (one-shot logs only fire once per restart, so
+# operators were missing ongoing drift between restarts). Counter is exposed
+# for the /usage debug section.
+_USAGE_SCHEMA_MISMATCH_COUNT = 0
+# #410: legacy boolean kept temporarily for any external code that imported
+# `_USAGE_SCHEMA_WARNED`. It now mirrors "count > 0" rather than gating
+# subsequent warnings — the new counter logs every call.
 _USAGE_SCHEMA_WARNED = False
 _USAGE_EXPECTED_WINDOW_FIELDS = frozenset({"utilization", "resets_at"})
 
 
+def get_usage_schema_mismatch_count() -> int:
+    """Return the running count of subscription-usage schema mismatches (#410).
+
+    Used by the ``/usage`` debug section. Tests reset by setting
+    ``_USAGE_SCHEMA_MISMATCH_COUNT = 0`` directly on the module.
+    """
+    return _USAGE_SCHEMA_MISMATCH_COUNT
+
+
 def _validate_usage_schema(data: dict[str, Any]) -> None:
-    """Log a one-shot warning if the subscription-usage payload is missing
+    """Log a warning every time the subscription-usage payload is missing
     expected fields. Does not mutate `data` — downstream code already handles
     missing sections defensively; this is purely an observability signal so
-    API-shape drift is noticed instead of silently ignored."""
-    global _USAGE_SCHEMA_WARNED
-    if _USAGE_SCHEMA_WARNED:
-        return
+    API-shape drift is noticed instead of silently ignored.
+
+    #410: changed from one-shot-per-process to per-call so the
+    issue-watcher fires for ongoing drift. The structlog event includes a
+    cumulative ``count`` field so callers can rate-limit on their side if
+    they want.
+    """
+    global _USAGE_SCHEMA_MISMATCH_COUNT, _USAGE_SCHEMA_WARNED
     missing: list[str] = []
     for window in ("five_hour", "seven_day"):
         section = data.get(window)
@@ -414,8 +473,13 @@ def _validate_usage_schema(data: dict[str, Any]) -> None:
             if field_name not in section
         )
     if missing:
+        _USAGE_SCHEMA_MISMATCH_COUNT += 1
         _USAGE_SCHEMA_WARNED = True
-        logger.warning("claude_usage.schema_mismatch", missing=missing)
+        logger.warning(
+            "claude_usage.schema_mismatch",
+            missing=missing,
+            count=_USAGE_SCHEMA_MISMATCH_COUNT,
+        )
 
 
 async def _maybe_append_usage_footer(
@@ -835,6 +899,14 @@ def __init__(
         self._stall_repeat_seconds: float = 180.0
         self._prev_recent_events: list[tuple[float, str]] | None = None
         self._frozen_ring_count: int = 0
+        # #481: heartbeat tick cadence. The stall monitor loop sleeps
+        # ``min(_heartbeat_interval, _stall_check_interval)`` per tick, so
+        # in production ticks fire every 30 s instead of 60 s; the stall
+        # threshold + ``_stall_repeat_seconds`` wall-clock gates still
+        # control warning frequency unchanged.
+        self._heartbeat_interval: float = 30.0
+        # #481: bash grace window for the stall_bash_grace_suppressed branch.
+        self._bash_grace_seconds: float = 60.0
         # Stuck-after-tool_result detector (#322). Instance overrides of the
         # class-level defaults, populated from WatchdogSettings in
         # handle_message.
@@ -867,16 +939,148 @@ async def _monitor() -> None:
             await self._run_loop(bg_tg)
             stall_scope.cancel()
 
+    def _heartbeat_tick(self) -> None:
+        """#481: per-tick visibility refresh.
+
+        Runs on EVERY monitor loop tick (both heartbeat-only and stall-check
+        ticks). Three responsibilities, none of which touch stall counters:
+
+        1. Mutate ``action.detail['countdown_s']`` for any open
+           ScheduleWakeup/Monitor action whose deadline lives in
+           ``engine_state.live_wakeups`` / ``live_monitors``. The verbose
+           detail formatter reads this on the next render.
+        2. Fire the post-result closing message exactly once when the
+           Claude watchdog has stamped ``post_result_closed_at`` (#470).
+        3. Bump ``event_seq`` to wake the render loop when any open action
+           is older than 60 s — this keeps the elapsed-time tail current
+           in the chat (otherwise the message looks frozen during long
+           BashOutput polling cycles).
+        """
+        stream = self.stream
+        engine_state = getattr(stream, "engine_state", None) if stream else None
+        live_wakeups = (
+            getattr(engine_state, "live_wakeups", None) if engine_state else None
+        )
+        live_monitors = (
+            getattr(engine_state, "live_monitors", None) if engine_state else None
+        )
+        now = self.clock()
+        # 1) Countdown mutation — ScheduleWakeup + Monitor.
+        if live_wakeups or live_monitors:
+            for action_state in self.tracker._actions.values():
+                if action_state.completed:
+                    continue
+                aid = str(action_state.action.id or "")
+                if not aid:
+                    continue
+                deadline: float | None = None
+                if live_wakeups and aid in live_wakeups:
+                    deadline = live_wakeups[aid]
+                elif live_monitors and aid in live_monitors:
+                    deadline = live_monitors[aid]
+                if deadline is None:
+                    continue
+                # Deadline 0.0 = unknown → leave countdown_s unset so the
+                # formatter falls back to delaySeconds-from-input rendering.
+                if deadline > 0:
+                    action_state.action.detail["countdown_s"] = max(0.0, deadline - now)
+
+        # 2) Post-result closing message — one-shot.
+        if (
+            engine_state is not None
+            and getattr(engine_state, "post_result_closed_at", None) is not None
+            and not getattr(engine_state, "post_result_closing_sent", False)
+        ):
+            mins = int(getattr(engine_state, "post_result_idle_minutes", 0.0))
+            text = f"✓ turn complete · session closed after {mins}m idle"
+            with contextlib.suppress(
+                anyio.WouldBlock,
+                anyio.BrokenResourceError,
+                anyio.ClosedResourceError,
+            ):
+                self.signal_send.send_nowait(None)
+            # Schedule the actual transport.send via the run loop's task
+            # group — the heartbeat tick is sync inside _stall_monitor's
+            # async loop, so we just stash a flag and let the caller fire
+            # the actual send (next tick reads post_result_closing_sent).
+            engine_state.post_result_closing_sent = True
+            # Hand the message off to the bridge's async send via a
+            # one-element queue field.
+            self._pending_closing_message = text
+
+        # 3) Long-running tail refresh — bump event_seq so the renderer
+        #    redraws with the fresh elapsed-time tail.
+        for action_state in self.tracker._actions.values():
+            if action_state.completed:
+                continue
+            if action_state.started_at == 0.0:
+                continue
+            if (now - action_state.started_at) > 60.0:
+                self._bump_heartbeat()
+                break
+
+    async def _flush_pending_closing_message(self) -> None:
+        """#470: send the one-shot post-result closing Telegram message.
+
+        Called from _stall_monitor after _heartbeat_tick. Idempotent — the
+        ``_pending_closing_message`` field is None except for the single
+        tick after the watchdog stamps post_result_closed_at.
+        """
+        text = getattr(self, "_pending_closing_message", None)
+        if not text:
+            return
+        self._pending_closing_message = None
+        try:
+            await self.transport.send(
+                channel_id=self.channel_id,
+                message=RenderedMessage(text=text),
+                options=SendOptions(thread_id=self.thread_id),
+            )
+        except Exception:  # noqa: BLE001
+            logger.debug(
+                "progress_edits.post_result_closing_send_failed", exc_info=True
+            )
+
     async def _stall_monitor(self) -> None:
-        """Periodically check for event stalls, log diagnostics, and notify."""
+        """Periodically check for event stalls, log diagnostics, and notify.
+
+        Two cadences (#481):
+        - **Heartbeat tick** every ``_heartbeat_interval`` (default 30 s):
+          updates countdowns, fires closing message, refreshes elapsed
+          tail. No stall counters touched.
+        - **Stall check** every ``_stall_check_interval`` (default 60 s):
+          full diagnostics, threshold selection, suppression matrix,
+          notification or auto-cancel.
+
+        The loop sleeps ``min(heartbeat_interval, stall_check_interval)``
+        per tick. The stall path runs only when enough wall-clock has
+        elapsed since the last stall check, preserving the existing
+        ``stall_repeat_seconds`` ≈ 3-tick math the test suite relies on.
+        """
         from .utils.proc_diag import (
             collect_proc_diag,
             is_cpu_active,
             is_tree_cpu_active,
         )
 
+        # Initialise pending closing-message slot used by _heartbeat_tick.
+        self._pending_closing_message: str | None = None
+
         while True:
-            await anyio.sleep(self._stall_check_interval)
+            # #481: tick at the FASTER of the two cadences — heartbeat
+            # (30 s default) drives the long-running tail and closing
+            # message; stall warnings still gate themselves at wall-clock
+            # ``_stall_repeat_seconds`` (180 s default) so faster ticks
+            # don't cause warning spam (the gate at line 992-993 below
+            # bails out when too soon to repeat). Tests that override
+            # ``_stall_check_interval`` to 0.01 s still get fast ticks.
+            tick_interval = min(self._heartbeat_interval, self._stall_check_interval)
+            await anyio.sleep(tick_interval)
+
+            # Heartbeat tick — cheap (no proc_diag, just dict scans).
+            self._heartbeat_tick()
+            await self._flush_pending_closing_message()
+
             # #203: piggy-back a TTL sweep of module-level registries on this
             # periodic tick.  Cheap when idle (empty dicts → early return).
             sweep_stale_registries()
@@ -939,6 +1143,26 @@ async def _stall_monitor(self) -> None:
             self._total_stall_warn_count += 1
             self._last_stall_warn_at = now
 
+            # #470/#481: compute the 5 expected-wait booleans once. Used to
+            # gate BOTH the auto-cancel arm (below) and the notification
+            # branches (further down — those add a ``not frozen_escalate``
+            # master gate so genuinely-frozen sessions still warn). Auto-
+            # cancel is gated unconditionally — a session that's about to
+            # gracefully close (#470 watchdog) or legitimately waiting on
+            # a pending timer (#481) must not be killed.
+            _post_result_idle = self._is_post_result_idle()
+            _wakeup_state = self._has_pending_wakeup()
+            _monitor_state = self._has_active_monitor()
+            _bash_grace = self._has_recent_bash_action(self._bash_grace_seconds)
+            _bash_fresh = self._has_fresh_bash_output(threshold / 2.0)
+            _expected_wait = (
+                _post_result_idle
+                or _wakeup_state is not None
+                or _monitor_state is not None
+                or _bash_grace
+                or _bash_fresh
+            )
+
             last_action = self._last_action_summary()
 
             recent = list(self.stream.recent_events) if self.stream else []
@@ -969,7 +1193,15 @@ async def _stall_monitor(self) -> None:
                 stderr_hint=stderr_hint,
             )
 
-            # Auto-cancel: dead process, no-PID zombie, or absolute cap
+            # Auto-cancel: dead process, no-PID zombie, or absolute cap.
+            # #470/#481: when an expected-wait state is active, skip the
+            # ``max_warnings`` arm — auto-cancel was designed for "the
+            # subprocess is stuck", not for "the watchdog is doing its job"
+            # (post-result idle) or "we're waiting on a legitimate timer"
+            # (ScheduleWakeup/Monitor/Bash polling). The ``process_dead``
+            # and ``no_pid_no_events`` arms still fire — those mean the
+            # subprocess actually crashed/never started, which is fatal
+            # regardless of the wait state.
             auto_cancel_reason: str | None = None
             if diag and diag.alive is False:
                 auto_cancel_reason = "process_dead"
@@ -979,6 +1211,23 @@ async def _stall_monitor(self) -> None:
                 and self._stall_warn_count >= self._STALL_MAX_WARNINGS_NO_PID
             ):
                 auto_cancel_reason = "no_pid_no_events"
+            elif _expected_wait:
+                # Don't auto-cancel during expected waits even if
+                # warn_count has accumulated. Each new tick will re-check
+                # whether the wait state still holds; once Claude resumes
+                # emitting events, _stall_warned resets via _last_event_at
+                # and the warn_count effectively rolls back.
+                logger.info(
+                    "progress_edits.stall_auto_cancel_suppressed_expected_wait",
+                    channel_id=self.channel_id,
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                    post_result=_post_result_idle,
+                    pending_wakeup=_wakeup_state is not None,
+                    active_monitor=_monitor_state is not None,
+                    bash_grace=_bash_grace,
+                    bash_fresh=_bash_fresh,
+                )
             elif self._stall_warn_count >= self._STALL_MAX_WARNINGS:
                 # Suppress auto-cancel when process is actively working
                 # (CPU ticks incrementing between diagnostic snapshots).
@@ -1087,7 +1336,68 @@ async def _stall_monitor(self) -> None:
                     self.signal_send.send_nowait(None)
                 continue
 
-            if cpu_active is True and not frozen_escalate and not main_sleeping:
+            # #470/#481: expected-wait suppression matrix. Gated by
+            # ``not frozen_escalate`` — a genuinely-frozen session
+            # (no JSONL events for 3+ stall ticks AND CPU still active)
+            # falls through to the existing notification path so the
+            # user gets a real warning. Each branch logs its own info
+            # event so journalctl can audit which rule fired. The
+            # heartbeat bump keeps the elapsed-time tail current
+            # without resetting stall counters.
+            if not frozen_escalate and _post_result_idle:
+                logger.info(
+                    "progress_edits.stall_post_result_suppressed",
+                    channel_id=self.channel_id,
+                    seconds_since_last_event=round(elapsed, 1),
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                )
+                self._bump_heartbeat()
+            elif not frozen_escalate and _wakeup_state is not None:
+                soonest, count = _wakeup_state
+                logger.info(
+                    "progress_edits.stall_schedule_wakeup_suppressed",
+                    channel_id=self.channel_id,
+                    seconds_since_last_event=round(elapsed, 1),
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                    soonest_remaining_s=round(soonest, 1),
+                    wakeup_count=count,
+                )
+                self._bump_heartbeat()
+            elif not frozen_escalate and _monitor_state is not None:
+                soonest, count = _monitor_state
+                logger.info(
+                    "progress_edits.stall_monitor_active_suppressed",
+                    channel_id=self.channel_id,
+                    seconds_since_last_event=round(elapsed, 1),
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                    soonest_remaining_s=round(soonest, 1),
+                    monitor_count=count,
+                )
+                self._bump_heartbeat()
+            elif not frozen_escalate and _bash_grace:
+                logger.info(
+                    "progress_edits.stall_bash_grace_suppressed",
+                    channel_id=self.channel_id,
+                    seconds_since_last_event=round(elapsed, 1),
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                    bash_grace_seconds=self._bash_grace_seconds,
+                )
+                self._bump_heartbeat()
+            elif not frozen_escalate and _bash_fresh:
+                logger.info(
+                    "progress_edits.stall_long_bash_suppressed",
+                    channel_id=self.channel_id,
+                    seconds_since_last_event=round(elapsed, 1),
+                    stall_warn_count=self._stall_warn_count,
+                    pid=self.pid,
+                    freshness_threshold_s=round(threshold / 2.0, 1),
+                )
+                self._bump_heartbeat()
+            elif cpu_active is True and not frozen_escalate and not main_sleeping:
                 logger.info(
                     "progress_edits.stall_suppressed_notification",
                     channel_id=self.channel_id,
@@ -1282,6 +1592,175 @@ async def _stall_monitor(self) -> None:
                         exc_info=True,
                     )
 
+    def _bump_heartbeat(self) -> None:
+        """Wake the render loop without changing stall counters or last_event_at.
+
+        Used by both existing CPU-active suppression branches (lines 1148-,
+        1179-, 1205-) and the new #481 suppression matrix. Idempotent —
+        the signal channel is buffer=1; subsequent send_nowait calls hit
+        WouldBlock harmlessly because the loop only re-renders if
+        rendered_seq != event_seq.
+        """
+        self.event_seq += 1
+        with contextlib.suppress(
+            anyio.WouldBlock,
+            anyio.BrokenResourceError,
+            anyio.ClosedResourceError,
+        ):
+            self.signal_send.send_nowait(None)
+
+    def _is_post_result_idle(self) -> bool:
+        """#470: suppression — Claude session is past its `result` event.
+
+        Returns True when ``stream.last_event_type == "result"`` AND
+        ``engine_state.result_received_at`` is armed (i.e. the post-result
+        idle watchdog is the legitimate owner of the silence). The
+        bidirectional CLI keeps stdin open between turns; the watchdog
+        will close it after ``post_result_idle_timeout``. Stall warnings
+        during that window are pure noise — and the auto-cancel arm would
+        otherwise wrongly kill a session that's about to gracefully close.
+
+        Stays engine-agnostic via getattr — engines without engine_state
+        no-op gracefully.
+        """
+        stream = self.stream
+        if stream is None:
+            return False
+        if getattr(stream, "last_event_type", None) != "result":
+            return False
+        engine_state = getattr(stream, "engine_state", None)
+        if engine_state is None:
+            return False
+        return getattr(engine_state, "result_received_at", None) is not None
+
+    def _has_pending_wakeup(self) -> tuple[float, int] | None:
+        """#481: suppression — ScheduleWakeup with future deadline.
+
+        Returns (soonest_remaining_seconds, count) when at least one entry
+        in ``engine_state.live_wakeups`` has a deadline still in the future
+        (or 0.0, which means the deadline is unknown but the wakeup is
+        armed — still a legitimate wait). Returns None otherwise.
+
+        ScheduleWakeup parks the Claude subprocess waiting for an upstream
+        timer fire (#289); during that wait Untether sees no JSONL events
+        but the silence is expected. This suppression only fires the
+        Telegram notification — the structlog WARN at line 1000 still
+        emits, so untether-issue-watcher and ops dashboards stay informed.
+        """
+        stream = self.stream
+        if stream is None:
+            return None
+        engine_state = getattr(stream, "engine_state", None)
+        if engine_state is None:
+            return None
+        live = getattr(engine_state, "live_wakeups", None)
+        if not live:
+            return None
+        now = self.clock()
+        soonest: float | None = None
+        for deadline in live.values():
+            # 0.0 = unknown deadline (legacy delay_ms fallback path or
+            # malformed input); treat as still-armed so we don't suppress
+            # the warning forever.
+            if deadline == 0.0:
+                soonest = 0.0
+                continue
+            remaining = deadline - now
+            if remaining <= 0:
+                continue
+            if soonest is None or remaining < soonest:
+                soonest = remaining
+        if soonest is None:
+            return None
+        return (soonest, len(live))
+
+    def _has_active_monitor(self) -> tuple[float, int] | None:
+        """#481: suppression — Monitor handle with future deadline.
+
+        Mirrors ``_has_pending_wakeup`` for ``engine_state.live_monitors``.
+        Monitor primitives park the subprocess on a child-process or
+        external-event watcher; legitimate silence until the deadline.
+        """
+        stream = self.stream
+        if stream is None:
+            return None
+        engine_state = getattr(stream, "engine_state", None)
+        if engine_state is None:
+            return None
+        live = getattr(engine_state, "live_monitors", None)
+        if not live:
+            return None
+        now = self.clock()
+        soonest: float | None = None
+        for deadline in live.values():
+            if deadline == 0.0:
+                soonest = 0.0
+                continue
+            remaining = deadline - now
+            if remaining <= 0:
+                continue
+            if soonest is None or remaining < soonest:
+                soonest = remaining
+        if soonest is None:
+            return None
+        return (soonest, len(live))
+
+    def _last_action_age(self) -> tuple[str | None, float | None]:
+        """Return (tool_name, age_seconds) for the most-recent open action.
+
+        Walks ``tracker._actions`` newest-first (insertion order in the
+        dict; the tracker doesn't reorder). Returns (None, None) when no
+        open action exists or when ``started_at`` is unset (legacy paths
+        without a clock).
+        """
+        for action_state in reversed(list(self.tracker._actions.values())):
+            if action_state.completed:
+                return (None, None)
+            name = action_state.action.detail.get("name") or action_state.action.title
+            tool_name = name if isinstance(name, str) else None
+            started_at = action_state.started_at
+            if started_at == 0.0:
+                return (tool_name, None)
+            return (tool_name, self.clock() - started_at)
+        return (None, None)
+
+    def _has_recent_bash_action(self, grace_s: float) -> bool:
+        """#481: suppression — Bash/BashOutput/KillShell within grace window.
+
+        Returns True when the most recent open action is a Bash-family
+        tool and its age is less than ``grace_s``. Covers the "command
+        is in its startup phase / first poll cycle" window where the
+        chat-side stall warning would be premature.
+        """
+        tool_name, age = self._last_action_age()
+        if tool_name is None or age is None:
+            return False
+        if tool_name not in ("Bash", "BashOutput", "KillShell"):
+            return False
+        return age < grace_s
+
+    def _has_fresh_bash_output(self, freshness_s: float) -> bool:
+        """#481: suppression — recent BashOutput tool_use within freshness_s.
+
+        BashOutput is Claude Code's mechanism for polling backgrounded
+        Bash shells; each call is a fresh tool_use+tool_result cycle. The
+        most-recent BashOutput's last_update_at signals "Claude got new
+        stdout from this bash recently", which IS the upstream proxy for
+        "the command isn't actually frozen". Returns True when any open
+        or recently-completed BashOutput action has last_update_at within
+        the freshness window.
+        """
+        now = self.clock()
+        for action_state in self.tracker._actions.values():
+            name = action_state.action.detail.get("name") or action_state.action.title
+            if name != "BashOutput":
+                continue
+            if action_state.last_update_at == 0.0:
+                continue
+            if (now - action_state.last_update_at) < freshness_s:
+                return True
+        return False
+
     def _has_pending_approval(self) -> bool:
         """Check if the most recent non-completed action is waiting for user approval."""
         for action_state in reversed(list(self.tracker._actions.values())):
@@ -1554,7 +2033,10 @@ async def _run_loop(self, bg_tg: anyio.abc.TaskGroup) -> None:
                 meta_formatter=format_meta_line,
             )
             rendered = self.presenter.render_progress(
-                state, elapsed_s=now - self.started_at, label=self.label
+                state,
+                elapsed_s=now - self.started_at,
+                label=self.label,
+                now=now,
             )
             # Detect approval button transitions for push notification
             new_kb = rendered.extra.get("reply_markup", {}).get("inline_keyboard", [])
@@ -2172,17 +2654,32 @@ async def handle_message(
     runner_text = _strip_resume_lines(incoming.text, is_resume_line=resume_strip)
     runner_text = _apply_preamble(runner_text)
 
-    progress_tracker = ProgressTracker(engine=runner.engine)
+    progress_tracker = ProgressTracker(engine=runner.engine, clock=clock)
     # rc4 (#271): seed trigger source into meta so the footer renders it.
     # The engine's own StartedEvent.meta merges onto this via note_event.
+    # rc6 (#271 follow-up): also render `at:<token>` from /at-scheduled runs
+    # with the alarm-clock icon — semantically a one-shot delayed cron.
     if context is not None and context.trigger_source:
         icon = (
             "\N{ALARM CLOCK}"
-            if context.trigger_source.startswith("cron:")
+            if context.trigger_source.startswith(("cron:", "at:"))
             else "\N{HIGH VOLTAGE SIGN}"
         )
         progress_tracker.meta = {"trigger": f"{icon} {context.trigger_source}"}
 
+    # #269: refresh progress settings on the default presenter so edits
+    # to [progress].max_actions / [progress].verbosity in untether.toml
+    # apply on the next run. Per-chat /verbose overrides downstream of
+    # _resolve_presenter() construct a fresh formatter from these refreshed
+    # values, so the override picks up the new defaults too.
+    progress_cfg = _load_progress_settings()
+    refresh = getattr(cfg.presenter, "refresh_progress_settings", None)
+    if callable(refresh):
+        try:
+            refresh(progress_cfg)
+        except Exception:  # noqa: BLE001
+            logger.debug("progress_settings.refresh_failed", exc_info=True)
+
     # Resolve effective presenter: check for per-chat verbose override
     effective_presenter = _resolve_presenter(cfg.presenter, incoming.channel_id)
 
@@ -2215,7 +2712,11 @@ async def handle_message(
         resume_formatter=runner.format_resume,
         context_line=context_line,
         thread_id=incoming.thread_id,
-        min_render_interval=cfg.min_render_interval,
+        # #269: read live each run so edits to [progress].min_render_interval
+        # apply on the next message without restart. cfg.min_render_interval
+        # is the startup snapshot and only used as fallback if the live load
+        # fails.
+        min_render_interval=progress_cfg.min_render_interval,
     )
 
     # Apply watchdog settings to runner and edits
@@ -2236,11 +2737,19 @@ async def handle_message(
         edits._stuck_after_tool_result_recovery_delay = (
             watchdog.stuck_after_tool_result_recovery_delay
         )
+        # #481: bash grace window for the stall_bash_grace_suppressed branch.
+        edits._bash_grace_seconds = watchdog.bash_grace_seconds
         if hasattr(runner, "_LIVENESS_TIMEOUT_SECONDS"):
             runner._LIVENESS_TIMEOUT_SECONDS = watchdog.liveness_timeout
         if hasattr(runner, "_stall_auto_kill"):
             runner._stall_auto_kill = watchdog.stall_auto_kill
 
+    # #481: heartbeat tick cadence — drives the long-running-action elapsed
+    # tail and the post-result closing-message poller. Read live so config
+    # reloads pick up new values on the next message (matches min_render_interval
+    # pattern above).
+    edits._heartbeat_interval = progress_cfg.heartbeat_interval
+
     running_task: RunningTask | None = None
     if running_tasks is not None and progress_ref is not None:
         running_task = RunningTask(context=context)
@@ -2449,26 +2958,14 @@ async def run_edits() -> None:
         return
     # --- End auto-continue ---
 
+    # #510: ``completed.answer`` already has the #508 ExitPlanMode
+    # plan-body prepend applied at the runner level (claude.py, on the
+    # per-stream path). The previous bridge-side prepend read
+    # ``runner.current_stream`` — a shared singleton on the ClaudeRunner
+    # — and leaked one chat's plan body into another concurrent chat's
+    # final answer.
     final_answer = completed.answer
 
-    # If there's a plan outline stored in a synthetic warning action,
-    # prepend it to the final answer so the user can read it.
-    # (The progress message that showed the outline gets replaced by
-    # the final message, so the outline would otherwise be lost.)
-    _outline_prefix = "Plan outline:\n"
-    for _action_state in progress_tracker.snapshot(
-        resume_formatter=runner.format_resume,
-        context_line=None,
-    ).actions:
-        _title = _action_state.action.title or ""
-        if _action_state.action.kind == "warning" and _title.startswith(
-            _outline_prefix
-        ):
-            _outline_body = _title[len(_outline_prefix) :]
-            if _outline_body.strip():
-                final_answer = f"{_outline_body}\n\n{final_answer}"
-            break
-
     # Auto-clear broken session: if a resumed run failed with 0 turns,
     # clear the saved session so the next message starts fresh.
     if run_ok is False and resume_token is not None and on_resume_failed is not None:
@@ -2550,6 +3047,7 @@ async def run_edits() -> None:
         engine=runner.engine,
         actions=progress_tracker.action_count,
         duration_ms=int(elapsed * 1000),
+        triggered=bool(context and context.trigger_source),
     )
     sync_resume_token(progress_tracker, completed.resume or outcome.resume)
 
diff --git a/src/untether/runners/amp.py b/src/untether/runners/amp.py
index 555f2689..636bcda9 100644
--- a/src/untether/runners/amp.py
+++ b/src/untether/runners/amp.py
@@ -322,7 +322,9 @@ class AmpRunner(ResumeTokenMixin, JsonlSubprocessRunner):
     amp_cmd: str = "amp"
     model: str | None = None
     mode: str | None = None
-    dangerously_allow_all: bool = True
+    # #206: default off — opt-in via [amp] config. Untether's permission layer
+    # is the primary control; AMP's own permission system is a defence in depth.
+    dangerously_allow_all: bool = False
     stream_json_input: bool = False
     session_title: str = "amp"
     logger = logger
@@ -548,7 +550,7 @@ def build_runner(config: EngineConfig, config_path: Path) -> Runner:
 
     dangerously_allow_all = config.get("dangerously_allow_all")
     if dangerously_allow_all is None:
-        dangerously_allow_all = True
+        dangerously_allow_all = False
     elif not isinstance(dangerously_allow_all, bool):
         logger.warning(
             "amp.config.invalid",
diff --git a/src/untether/runners/claude.py b/src/untether/runners/claude.py
index bdc9e082..a46b6599 100644
--- a/src/untether/runners/claude.py
+++ b/src/untether/runners/claude.py
@@ -26,6 +26,7 @@
 import msgspec
 
 from ..backends import EngineBackend, EngineConfig
+from ..config import ConfigError
 from ..events import EventFactory
 from ..logging import get_logger
 from ..model import (
@@ -64,6 +65,66 @@
     r"(?im)^\s*`?claude\s+(?:--resume|-r)\s+(?P<token>[^`\s]+)`?\s*$"
 )
 
+# Flags that Untether sets on every spawn (stream-json I/O, resume tokens,
+# permission wiring). A user-supplied copy in `[claude].extra_args` would
+# either duplicate the arg or collide with Untether's expected value, so
+# `build_runner` rejects any entry matching this set or one of the equivalent
+# `key=value` prefixes below. Mirrors `codex._EXEC_ONLY_FLAGS` (#407).
+_RESERVED_FLAGS: frozenset[str] = frozenset(
+    {
+        "-p",
+        "--print",
+        "--output-format",
+        "--input-format",
+        "--resume",
+        "-r",
+        "--continue",
+        "-c",
+        "--permission-mode",
+        "--permission-prompt-tool",
+    }
+)
+_RESERVED_PREFIXES: tuple[str, ...] = (
+    "--output-format=",
+    "--input-format=",
+    "--resume=",
+    "--permission-mode=",
+    "--permission-prompt-tool=",
+)
+
+
+def _find_reserved_flag(extra_args: list[str]) -> str | None:
+    for arg in extra_args:
+        if arg in _RESERVED_FLAGS:
+            return arg
+        for prefix in _RESERVED_PREFIXES:
+            if arg.startswith(prefix):
+                return arg
+    return None
+
+
+def _load_env_extras() -> tuple[tuple[str, ...], tuple[str, ...]]:
+    """#409: read [security] env_extra_allow / env_extra_prefix_allow.
+
+    Best-effort — config errors must never block a run, so we swallow
+    them and fall back to the built-in defaults. Returns
+    ``(extra_exact, extra_prefix)``.
+    """
+    from ..settings import load_settings_if_exists
+
+    try:
+        result = load_settings_if_exists()
+        if result is None:
+            return ((), ())
+        settings, _ = result
+        return (
+            tuple(settings.security.env_extra_allow),
+            tuple(settings.security.env_extra_prefix_allow),
+        )
+    except Exception:  # noqa: BLE001 — never let config errors block a run
+        return ((), ())
+
+
 # Phase 2: Global registry for active ClaudeRunner instances
 # Keyed by session_id, stores (runner_instance, timestamp)
 _ACTIVE_RUNNERS: dict[str, tuple[ClaudeRunner, float]] = {}
@@ -126,6 +187,19 @@
 _PENDING_ASK_REQUESTS: dict[str, tuple[int, str]] = {}
 
 
+def is_session_alive(session_id: str) -> bool:
+    """Return True if a Claude subprocess for ``session_id`` is currently
+    running and has an open stdin (registered in :data:`_SESSION_STDIN`).
+
+    Used by :mod:`untether.loop_scheduler` (#289) before firing a loop
+    iteration, to avoid racing a still-live subprocess that may be parked
+    on a control_request awaiting Telegram button input.  Once the
+    subprocess exits its registry entry is cleared in :class:`ClaudeRunner`'s
+    ``run_impl`` finally block.
+    """
+    return session_id in _SESSION_STDIN
+
+
 @dataclass(slots=True)
 class AskQuestionState:
     """Tracks multi-question AskUserQuestion flow state."""
@@ -185,6 +259,13 @@ class ClaudeStreamState:
     max_text_len_since_cooldown: int = 0
     # Store outline text for embedding in synthetic approve/deny action
     outline_text: str | None = None
+    # #508 ExitPlanMode plan body — captured from the tool_use input on
+    # every ExitPlanMode call so the bridge can re-emit it as part of the
+    # final answer when the post-approval result is brief or empty
+    # (research/audit tasks where Claude has nothing left to say after
+    # the user approves).  Plan messages on Telegram are deleted on
+    # approve, so this is the only path to retain the body.
+    last_exitplanmode_plan: str | None = None
     # Cumulative seconds the session spent in Anthropic-side rate-limit waits (#349).
     # Sum of every rate_limit_event's retry_after_ms, so the cost footer can annotate
     # "(incl. Xm Ys rate-limited)" when a run finishes after one or more throttles.
@@ -210,8 +291,20 @@ class ClaudeStreamState:
     live_bg_bashes: set[str] = field(default_factory=set)
     live_bg_agents: set[str] = field(default_factory=set)
     live_wakeups: dict[str, float] = field(default_factory=dict)
+    # #507 arm-time `delaySeconds` per ScheduleWakeup tool_use_id, captured
+    # parallel to ``live_wakeups``. ``live_wakeups`` stores future deadlines
+    # which are hard to invert after they pass, so the post-result idle
+    # watchdog reads this dict to shorten its timeout to ``max_delay + 60s``
+    # when /loop is OFF (the wakeup is then a silent no-op upstream).
+    live_wakeups_arm_delay: dict[str, float] = field(default_factory=dict)
     live_remote_triggers: set[str] = field(default_factory=set)
 
+    # #289 — first user message text for the run.  Populated by ``new_state``
+    # from the prompt arg.  Used as the fallback for the
+    # ``<<autonomous-loop-dynamic>>`` sentinel when ScheduleWakeup is
+    # observed without an explicit ``prompt`` field (Probe 3 result).
+    first_user_message_text: str | None = None
+
     # #361 env-leak audit: pid populated by ClaudeRunner.run_impl after
     # spawn so translate_claude_event can sample /proc/<pid>/environ in
     # the system.init handler. audited flips to True after the first
@@ -248,6 +341,25 @@ class ClaudeStreamState:
     pending_catalog_refresh_ids: list[str] = field(default_factory=list)
     catalog_refresh_seq: int = 0
 
+    # #333: monotonic timestamp of the most recent ``result`` event. The
+    # post-result idle watchdog (``ClaudeRunner._post_result_idle_watchdog``)
+    # polls this to decide when to close stdin. None until the first
+    # result lands; reset on each subsequent result so that a multi-turn
+    # bidirectional session re-arms the timer on every turn boundary.
+    result_received_at: float | None = None
+
+    # #470: cross-layer signals from _post_result_idle_watchdog → bridge.
+    # The watchdog stamps ``post_result_closed_at`` (monotonic) and
+    # ``post_result_idle_minutes`` immediately before closing stdin.
+    # ``ProgressEdits._stall_monitor`` polls these via engine_state
+    # duck-typing (mirrors the pattern at runner_bridge.py:1426 for
+    # ``has_live_background_work``) and fires a one-shot Telegram closing
+    # message with the elapsed-minutes wording, then sets
+    # ``post_result_closing_sent`` so subsequent ticks no-op (idempotent).
+    post_result_closed_at: float | None = None
+    post_result_idle_minutes: float = 0.0
+    post_result_closing_sent: bool = False
+
 
 def _normalize_tool_result(content: Any) -> str:
     if content is None:
@@ -347,11 +459,26 @@ def _register_background_handle(
     elif tool_name == "Agent" and bool(raw_input.get("run_in_background")):
         state.live_bg_agents.add(tool_id)
     elif tool_name == "ScheduleWakeup":
-        delay_ms = raw_input.get("delay_ms") or raw_input.get("timeout_ms")
-        if isinstance(delay_ms, (int, float)) and delay_ms > 0:
-            state.live_wakeups[tool_id] = time.monotonic() + (delay_ms / 1000.0)
+        # #481: the actual Claude Code ScheduleWakeup tool schema (per
+        # #289 / claude-agent-sdk-python) emits ``delaySeconds`` as the
+        # canonical field. Earlier versions of this code read
+        # ``delay_ms``/``timeout_ms`` only, which always missed in
+        # production (live_wakeups[tool_id] fell to 0.0 → countdown
+        # rendering broken, though membership-only suppression still
+        # worked). Read delaySeconds first; keep the legacy fallbacks so
+        # existing test fixtures parameterised on delay_ms still work.
+        delay_seconds_raw = raw_input.get("delaySeconds")
+        if isinstance(delay_seconds_raw, (int, float)) and delay_seconds_raw > 0:
+            state.live_wakeups[tool_id] = time.monotonic() + float(delay_seconds_raw)
+            state.live_wakeups_arm_delay[tool_id] = float(delay_seconds_raw)
         else:
-            state.live_wakeups[tool_id] = 0.0
+            delay_ms = raw_input.get("delay_ms") or raw_input.get("timeout_ms")
+            if isinstance(delay_ms, (int, float)) and delay_ms > 0:
+                state.live_wakeups[tool_id] = time.monotonic() + (delay_ms / 1000.0)
+                state.live_wakeups_arm_delay[tool_id] = delay_ms / 1000.0
+            else:
+                state.live_wakeups[tool_id] = 0.0
+                state.live_wakeups_arm_delay[tool_id] = 0.0
     elif tool_name == "RemoteTrigger":
         state.live_remote_triggers.add(tool_id)
 
@@ -362,9 +489,177 @@ def _clear_background_handle(state: ClaudeStreamState, tool_use_id: str) -> None
     state.live_bg_bashes.discard(tool_use_id)
     state.live_bg_agents.discard(tool_use_id)
     state.live_wakeups.pop(tool_use_id, None)
+    state.live_wakeups_arm_delay.pop(tool_use_id, None)
     state.live_remote_triggers.discard(tool_use_id)
 
 
+# ── /loop and ScheduleWakeup observation (#289) ─────────────────────────
+
+
+# Result-text patterns extracted in ``_observe_loop_tool_result``.
+# CronCreate / CronDelete share the ``\bjob ([0-9a-f]{8})\b`` form (Probe 5).
+_LOOP_CRON_ID_RE = re.compile(r"\bjob ([0-9a-f]{8})\b")
+# ScheduleWakeup result text reports the runtime-clamped delay as ``(in Ns)``.
+_LOOP_WAKEUP_DELAY_RE = re.compile(r"\(in (\d+)s\)")
+
+
+def _loop_enabled_for_chat(chat_id: int | None) -> bool:
+    """Resolve the /loop master toggle for a chat.
+
+    Resolution order (matches the design doc §5.0):
+
+    1. Per-chat override via ``EngineRunOptions.loop_enabled`` (set by
+       ``/config → 🔁 Loop mode``).  ``None`` means "follow global".
+    2. Global ``[loop] enabled`` from ``untether.toml``.
+    3. Hard fallback: ``False`` so a config error never accidentally
+       turns Loop mode on.
+
+    ``chat_id`` is currently advisory — the per-chat override lives in
+    the run-options contextvar set by ``executor.handle_engine_run``,
+    which is already chat-scoped.  We accept it so the call site reads
+    cleanly and so a future per-chat resolver can be wired in without
+    changing observer signatures.
+    """
+    options = get_run_options()
+    if options is not None and options.loop_enabled is not None:
+        return bool(options.loop_enabled)
+    try:
+        result = load_settings_if_exists()
+        if result is None:
+            return False
+        settings, _ = result
+        return bool(settings.loop.enabled)
+    except Exception:  # noqa: BLE001 — never let config errors turn loop ON
+        return False
+
+
+def _observe_loop_tool_use(
+    state: ClaudeStreamState,
+    content: claude_schema.StreamToolUseBlock,
+) -> None:
+    """Observe ``CronCreate`` / ``ScheduleWakeup`` / ``CronDelete``
+    ``tool_use`` events and register Untether-side loop entries (#289).
+
+    Sibling of :func:`_register_background_handle` — does NOT mutate
+    ``state.live_*`` registries.  Called after
+    :func:`_register_background_handle` so the rc8 ScheduleWakeup
+    countdown still works for short waits when Loop mode is OFF.
+    """
+    from ..utils.paths import get_run_channel_id
+
+    chat_id = get_run_channel_id()
+    if chat_id is None:
+        return  # not in a chat-scoped run (probes, ad-hoc spawns)
+    if not _loop_enabled_for_chat(chat_id):
+        return  # master toggle off → behave as today
+    tool_name = str(content.name or "")
+    tool_id = content.id
+    raw_input = content.input if isinstance(content.input, dict) else {}
+    session_id = state.factory.resume.value if state.factory.resume else None
+    if not session_id:
+        return  # session_id only known after system.init; tool_use shouldn't
+        # arrive before that, but guard defensively
+
+    from .. import loop_scheduler
+
+    if tool_name == "CronCreate":
+        # Probe 5: input field is `cron`, NOT `cron_expression`.  Lenient
+        # fallback to `cron_expression`/`schedule` in case the upstream
+        # schema gains aliases later.
+        cron_expr = (
+            raw_input.get("cron")
+            or raw_input.get("cron_expression")
+            or raw_input.get("schedule")
+        )
+        prompt = raw_input.get("prompt") or raw_input.get("text") or ""
+        recurring = bool(raw_input.get("recurring", True))
+        if not cron_expr or not prompt:
+            return
+        try:
+            loop_scheduler.register_pending_cron(
+                session_id=session_id,
+                tool_use_id=tool_id,
+                cron_expression=str(cron_expr),
+                prompt=str(prompt),
+                recurring=recurring,
+                chat_id=int(chat_id),
+                fallback_first_user_message=state.first_user_message_text,
+            )
+        except loop_scheduler.LoopSchedulerError as exc:
+            logger.warning(
+                "loop.observe.cron_register_failed",
+                session=session_id,
+                error=str(exc),
+            )
+    elif tool_name == "ScheduleWakeup":
+        # Probe 5: minimum delaySeconds = 60 (runtime clamps shorter values).
+        delay_seconds_raw = raw_input.get("delaySeconds")
+        if not isinstance(delay_seconds_raw, (int, float)) or delay_seconds_raw <= 0:
+            return
+        # Inline threshold — short waits stay rendered live by the
+        # rc8 countdown without an Untether-side timer (post-result
+        # watchdog won't reach them).
+        try:
+            settings_result = load_settings_if_exists()
+            inline_threshold = (
+                settings_result[0].loop.inline_threshold_seconds
+                if settings_result is not None
+                else 300
+            )
+        except Exception:  # noqa: BLE001
+            inline_threshold = 300
+        if delay_seconds_raw <= inline_threshold:
+            return
+        prompt = raw_input.get("prompt") or "<<autonomous-loop-dynamic>>"
+        try:
+            loop_scheduler.register_pending_wakeup(
+                session_id=session_id,
+                tool_use_id=tool_id,
+                delay_seconds=float(delay_seconds_raw),
+                prompt=str(prompt),
+                chat_id=int(chat_id),
+                fallback_first_user_message=state.first_user_message_text,
+            )
+        except loop_scheduler.LoopSchedulerError as exc:
+            logger.warning(
+                "loop.observe.wakeup_register_failed",
+                session=session_id,
+                error=str(exc),
+            )
+    elif tool_name == "CronDelete":
+        # Probe 5: input field is `id`, NOT `taskId`/`cronId`.
+        upstream_id = raw_input.get("id") or raw_input.get("taskId")
+        if upstream_id:
+            loop_scheduler.cancel_by_upstream_id(str(upstream_id))
+
+
+def _observe_loop_tool_result(
+    state: ClaudeStreamState,
+    tool_use_id: str,
+    result_content: object,
+) -> None:
+    """Observe ``CronCreate`` ``tool_result`` events and bind the upstream
+    8-character cron ID to the matching pending entry (#289).
+
+    Sibling of :func:`_clear_background_handle`.  Does nothing if no
+    matching entry exists (e.g. master toggle was off when tool_use was
+    observed).  Idempotent — bind_upstream_id is a no-op for unknown
+    tool_use_ids.
+    """
+    if not isinstance(result_content, str):
+        # tool_result.content can be list[dict] for multi-block results.
+        # CronCreate / ScheduleWakeup return free-form strings, so anything
+        # else is irrelevant.
+        return
+    from .. import loop_scheduler
+
+    match = _LOOP_CRON_ID_RE.search(result_content)
+    if match is None:
+        return
+    upstream_id = match.group(1)
+    loop_scheduler.bind_upstream_id(tool_use_id, upstream_id)
+
+
 def has_live_background_work(state: ClaudeStreamState) -> bool:
     """Return True when the session has any background handle whose deadline
     (if any) is still in the future (#346 gate).
@@ -496,6 +791,51 @@ def _truncate(text: str, max_len: int) -> str:
     return ""
 
 
+# #438: classify Stream idle timeout failures so the user sees actionable
+# context instead of just "API Error: Stream idle timeout - partial response
+# received". Two distinct upstream Anthropic API failure modes:
+#
+# - Type A — mid-generation stall: the model emitted some output, then went
+#   silent for >CLAUDE_STREAM_IDLE_TIMEOUT_MS. ``num_turns >= 1`` and
+#   ``duration_api_ms > 0``. Often legitimate long opus 4.7 1M plan-mode
+#   reasoning that exceeded the watchdog; raising the timeout helps.
+#
+# - Type B — cold-start zero-byte stall: zero bytes ever arrived. ``num_turns
+#   <= 1`` and ``duration_api_ms == 0``. The watchdog correctly detected an
+#   API outage from the client's perspective; raising the timeout does NOT
+#   help. Likely Anthropic API queueing / availability under load.
+#
+# See #438 for upstream tracking (consolidated `claude-code` issues
+# 2026-04-17→26).
+_STREAM_IDLE_TIMEOUT_PATTERN = "Stream idle timeout"
+
+
+def _classify_stream_idle_timeout(
+    event: claude_schema.StreamResultMessage,
+) -> str | None:
+    """Return a short Type-A / Type-B annotation, or None if not a stall."""
+    result = event.result if isinstance(event.result, str) else ""
+    if _STREAM_IDLE_TIMEOUT_PATTERN not in result:
+        return None
+    if event.num_turns <= 1 and (
+        event.duration_api_ms is None or event.duration_api_ms == 0
+    ):
+        # Type B — cold-start zero-byte stall. No bytes from API.
+        return (
+            "🌐 Cold-start API stall (Type B): Anthropic API returned no "
+            "bytes within the watchdog window. Likely upstream API "
+            "queueing/availability — raising CLAUDE_STREAM_IDLE_TIMEOUT_MS "
+            "will NOT help. Retry shortly."
+        )
+    # Type A — mid-generation stall. Model emitted output then went silent.
+    return (
+        "⏳ Mid-generation API stall (Type A): SSE stream went silent after "
+        "partial output. Often legitimate long reasoning that exceeded the "
+        "watchdog — consider raising [watchdog] claude_stream_idle_timeout_ms "
+        "in untether.toml."
+    )
+
+
 def _extract_error(
     event: claude_schema.StreamResultMessage,
     *,
@@ -511,6 +851,11 @@ def _extract_error(
     else:
         first = "Claude Code run failed"
 
+    # #438: append a Type-A / Type-B annotation when the failure is a
+    # Stream idle timeout, so the operator can tell the two failure modes
+    # apart from the visible message alone.
+    classification = _classify_stream_idle_timeout(event)
+
     # Second line: diagnostic context
     parts: list[str] = []
     sid = event.session_id[:8] if event.session_id else None
@@ -524,7 +869,57 @@ def _extract_error(
     if event.duration_api_ms:
         parts.append(f"api: {event.duration_api_ms}ms")
 
-    return f"{first}\n{' · '.join(parts)}"
+    diagnostics = " · ".join(parts)
+    if classification is not None:
+        return f"{first}\n{diagnostics}\n\n{classification}"
+    return f"{first}\n{diagnostics}"
+
+
+_PREPEND_LENGTH_GATE = 600
+_PREPEND_BODY_CAP = 1500
+_PREPEND_BODY_TRUNC_SUFFIX = "\n\n…\n\n(plan truncated — shown in full during approval)"
+
+
+def _prepend_exitplanmode_plan(final_answer: str | None, plan_body: str | None) -> str:
+    """#508 Re-emit ExitPlanMode plan body in the final answer.
+
+    Called from the per-stream ``StreamResultMessage`` translation path
+    (#510) using ``state.last_exitplanmode_plan`` — correctly scoped to
+    this run's stream, not the shared ``runner.current_stream`` singleton.
+
+    #515 length-gate tuning (rc13). The original substring check
+    (``body in final_answer``) failed in practice because the rc11
+    preamble told Claude to *paraphrase* the plan post-approval rather
+    than literal-copy it, so the skip never triggered and Layer E
+    concatenated the full plan body in front of every well-behaved run
+    (42k-char Telegram messages on staging). The new preamble asks for a
+    brief CLI-style summary post-approval — when Claude obeys, the
+    answer is >600 chars and we skip the prepend; when Claude exits with
+    nothing substantive (the original #508 repro at 584 chars), the
+    length gate falls through and we prepend a capped plan body.
+
+    Skip rules (in order):
+    1. ``plan_body`` empty/whitespace → return final answer as-is.
+    2. ``final_answer`` already substantive (≥ ``_PREPEND_LENGTH_GATE``)
+       → skip prepend, post-approval text is doing the job.
+    3. Exact substring match → skip prepend (cheap belt-and-braces).
+    4. Otherwise prepend, truncating ``plan_body`` to
+       ``_PREPEND_BODY_CAP`` chars so a runaway plan body doesn't ship
+       a 30k-char final.
+    """
+    if not plan_body or not plan_body.strip():
+        return final_answer or ""
+    final = final_answer or ""
+    if len(final) >= _PREPEND_LENGTH_GATE:
+        return final
+    body = plan_body.strip()
+    if body in final:
+        return final
+    if len(body) > _PREPEND_BODY_CAP:
+        body = body[:_PREPEND_BODY_CAP].rstrip() + _PREPEND_BODY_TRUNC_SUFFIX
+    if final:
+        return f"📋 Plan (approved):\n\n{body}\n\n---\n\n{final}"
+    return f"📋 Plan (approved):\n\n{body}"
 
 
 def _maybe_audit_env(state: ClaudeStreamState, session_id: str) -> None:
@@ -550,7 +945,15 @@ def _maybe_audit_env(state: ClaudeStreamState, session_id: str) -> None:
     if not enabled:
         return
 
-    leaked = audit_proc_env(state.pid, expected_extras=("UNTETHER_SESSION",))
+    # #409: pass user extras through so the audit doesn't flag names the
+    # operator explicitly opted into via [security] env_extra_allow.
+    user_exact, user_prefix = _load_env_extras()
+    leaked = audit_proc_env(
+        state.pid,
+        expected_extras=("UNTETHER_SESSION",),
+        user_extra_exact=user_exact,
+        user_extra_prefix=user_prefix,
+    )
     for name in leaked:
         if name in state.audited_leaks:
             continue
@@ -677,7 +1080,14 @@ def translate_claude_event(
             out: list[UntetherEvent] = []
             for content in message.content:
                 match content:
-                    case claude_schema.StreamToolUseBlock():
+                    case (
+                        claude_schema.StreamToolUseBlock()
+                        | claude_schema.StreamServerToolUseBlock()
+                    ):
+                        # #489 server_tool_use shares the tool_use translation —
+                        # _register_background_handle / _observe_loop_tool_use
+                        # filter on tool name and no-op for unrecognised server
+                        # tools (web_search, code_execution, computer_use, …).
                         action = _tool_action(
                             content,
                             parent_tool_use_id=parent_tool_use_id,
@@ -687,6 +1097,24 @@ def translate_claude_event(
                         # #347 track long-running primitives that outlive
                         # this tool_use → tool_result cycle
                         _register_background_handle(state, content)
+                        # #289 observe /loop and ScheduleWakeup tool calls
+                        # so Untether can re-fire after the subprocess exits
+                        # (master toggle gate inside).  Sibling of, not
+                        # replacement for, _register_background_handle.
+                        _observe_loop_tool_use(state, content)
+                        # #508 capture ExitPlanMode plan body so the bridge
+                        # can re-emit it in the final answer when the
+                        # post-approval result is brief/empty (research
+                        # tasks).  Only captures from the regular Approve
+                        # flow — Pause-and-Outline outlines go via
+                        # state.outline_text and a different code path.
+                        if str(content.name or "") == "ExitPlanMode":
+                            _epm_input = (
+                                content.input if isinstance(content.input, dict) else {}
+                            )
+                            _plan_body = _epm_input.get("plan")
+                            if isinstance(_plan_body, str) and _plan_body.strip():
+                                state.last_exitplanmode_plan = _plan_body
                         out.append(
                             factory.action_started(
                                 action_id=action.id,
@@ -740,12 +1168,22 @@ def translate_claude_event(
             out: list[UntetherEvent] = []
             saw_tool_result = False
             for content in message.content:
-                if not isinstance(content, claude_schema.StreamToolResultBlock):
+                # #489 advisor_tool_result shares the tool_result translation.
+                if not isinstance(
+                    content,
+                    (
+                        claude_schema.StreamToolResultBlock,
+                        claude_schema.StreamAdvisorToolResultBlock,
+                    ),
+                ):
                     continue
                 saw_tool_result = True
                 tool_use_id = content.tool_use_id
                 # #347 clear any background-task entry for this tool_use_id
                 _clear_background_handle(state, tool_use_id)
+                # #289 bind upstream cron ID so CronDelete observations
+                # later in the session can target the right loop entry.
+                _observe_loop_tool_result(state, tool_use_id, content.content)
                 action = state.pending_actions.pop(tool_use_id, None)
                 if action is None:
                     action = Action(
@@ -791,11 +1229,41 @@ def translate_claude_event(
             if ok and not result_text and state.last_assistant_text:
                 result_text = state.last_assistant_text
 
+            # #510 / #508: re-emit the ExitPlanMode plan body when the
+            # post-approval final answer is brief/empty. Done HERE on the
+            # per-stream path (state is per-run, correctly scoped) rather
+            # than in runner_bridge.handle_message against the shared
+            # runner.current_stream singleton — which raced across
+            # concurrent Claude chats and leaked plan bodies cross-chat.
+            if ok:
+                result_text = _prepend_exitplanmode_plan(
+                    result_text, state.last_exitplanmode_plan
+                )
+
             resume = ResumeToken(engine=ENGINE, value=event.session_id)
             error = None if ok else _extract_error(event, resumed=state.resumed)
             usage = _usage_payload(event)
 
-            return [
+            # #333: arm the post-result idle watchdog. Reset on every
+            # result (multi-turn re-arms the timer per turn boundary).
+            state.result_received_at = time.monotonic()
+
+            events_out: list[UntetherEvent] = []
+            # #333 UX signal #1: append "✓ turn complete" to the meta
+            # footer so the user immediately sees the turn is done and
+            # the session is now waiting for the next prompt. A
+            # supplementary StartedEvent with new meta is the supported
+            # pattern for late-arriving metadata (see
+            # .claude/rules/runner-development.md).
+            if ok:
+                events_out.append(
+                    factory.started(
+                        resume,
+                        title=None,
+                        meta={"complete": "✓ turn complete"},
+                    )
+                )
+            events_out.append(
                 factory.completed(
                     ok=ok,
                     answer=result_text,
@@ -803,9 +1271,49 @@ def translate_claude_event(
                     error=error,
                     usage=usage or None,
                 )
-            ]
+            )
+            return events_out
         case claude_schema.StreamControlRequest(request_id=request_id, request=request):
-            # Auto-approve non-user-facing control requests
+            # Auto-approve non-user-facing control requests.
+            #
+            # #380 — security audit (2026-04-27) verified the safety invariant
+            # for the two subtypes that look superficially scary:
+            #
+            # * `ControlMcpMessageRequest` (subtype=mcp_message). Carries
+            #   `server_name: str` + `message: Any`. Untether NEVER inspects
+            #   or executes the `message` payload — it auto-acknowledges and
+            #   the payload flows through Claude Code to the model, where
+            #   model-initiated tool calls still pass through the standard
+            #   `ControlCanUseToolRequest` gate (and ExitPlanMode / interactive
+            #   approval where applicable). A compromised MCP server CAN send
+            #   tainted prompts via this channel, but that's the inherent
+            #   threat model of any MCP server — not specific to auto-approve.
+            #   Routing this through Telegram approval would not block the
+            #   payload (it's already in-flight) — it would just delay the
+            #   acknowledgement, with no security gain.
+            #
+            # * `ControlRewindFilesRequest` (subtype=rewind_files). Carries
+            #   `user_message_id: str`. Rewind is initiated by the user via
+            #   the Claude CLI's `/rewind` slash command (or programmatic
+            #   equivalent) — the model cannot autonomously trigger rewind
+            #   in upstream Claude Code 2.1.x. Untether currently has no UI
+            #   that issues `/rewind`, so this control_request only fires
+            #   when the user types `/rewind` themselves in a chat; the user
+            #   has already consented. If a future release exposes rewind
+            #   via Telegram UI, that UI's command handler should provide
+            #   the gate, not this control-channel layer. The denial state
+            #   that drove a prior approval/deny decision lives on the
+            #   parent (Untether) side in `_HANDLED_REQUESTS` /
+            #   `_PLAN_EXIT_APPROVED` — those are NOT mutated by rewind.
+            #
+            # The other three (initialize, hook_callback, interrupt) are
+            # protocol housekeeping with no payload that Untether interprets.
+            #
+            # Acceptance: changes to either subtype's semantics in upstream
+            # Claude Code MUST trigger a re-audit. Tests in
+            # tests/test_claude_control.py::TestAutoApproveSafetyInvariant
+            # lock in the expectation that auto-approve runs without
+            # invoking any callback that observes the payload.
             _AUTO_APPROVE_TYPES = (
                 claude_schema.ControlInitializeRequest,
                 claude_schema.ControlHookCallbackRequest,
@@ -1381,6 +1889,7 @@ class ClaudeRunner(ResumeTokenMixin, JsonlSubprocessRunner):
     model: str | None = None
     permission_mode: str | None = None
     allowed_tools: list[str] | None = None
+    extra_args: list[str] = field(default_factory=list)
     dangerously_skip_permissions: bool = False
     use_api_billing: bool = False
     session_title: str = "claude"
@@ -1551,6 +2060,12 @@ def _build_args(self, prompt: str, resume: ResumeToken | None) -> list[str]:
                 "--verbose",
             ]
 
+        # User-supplied CLI flags (e.g. `--chrome` to opt into Claude-in-Chrome).
+        # Must sit after the Untether-managed I/O prelude but before
+        # resume / model / effort / allowed-tools / permission so the final
+        # prompt position (after `--`) is never displaced (#407).
+        args.extend(self.extra_args)
+
         if resume is not None:
             if resume.is_continue:
                 args.append("--continue")
@@ -1631,9 +2146,13 @@ def env(self, *, state: Any) -> dict[str, str] | None:
         # MCP namespaces, etc.) flow through. See env_policy.py for the
         # canonical list + how to extend it when a new MCP or engine needs
         # an unfamiliar variable.
-        from ..utils.env_policy import filtered_env
+        from ..utils.env_policy import filtered_env, log_user_extensions_once
 
-        env = filtered_env()
+        # #409: thread per-deployment extras from
+        # [security] env_extra_allow / env_extra_prefix_allow.
+        extra_exact, extra_prefix = _load_env_extras()
+        log_user_extensions_once(extra_exact, extra_prefix)
+        env = filtered_env(extra_allow=extra_exact, extra_prefix=extra_prefix)
         # Let Claude Code hooks detect Untether sessions (e.g. PitchDocs
         # context-guard skips blocking Stop hooks in Telegram).
         env["UNTETHER_SESSION"] = "1"
@@ -1649,7 +2168,22 @@ def env(self, *, state: Any) -> dict[str, str] | None:
         # matches the undici idle-body timeout that motivated #322 *and*
         # Untether's own `stuck_after_tool_result_timeout` default, so the
         # upstream CLI watchdog and our detector fire in the same window.
-        env.setdefault("CLAUDE_STREAM_IDLE_TIMEOUT_MS", "300000")
+        # #438: now user-configurable via [watchdog] claude_stream_idle_timeout_ms
+        # so deployments hitting upstream Anthropic API stalls can ride out
+        # longer silences. setdefault still respects shell-set overrides.
+        idle_timeout_default = "300000"
+        try:
+            result = load_settings_if_exists()
+            if result is not None:
+                settings, _ = result
+                idle_timeout_default = str(
+                    settings.watchdog.claude_stream_idle_timeout_ms
+                )
+        except Exception:  # noqa: BLE001 — settings errors must not block a run
+            logger.debug(
+                "claude_stream_idle_timeout.settings_load_failed", exc_info=True
+            )
+        env.setdefault("CLAUDE_STREAM_IDLE_TIMEOUT_MS", idle_timeout_default)
         env.setdefault("MCP_TOOL_TIMEOUT", "120000")
         env.setdefault("MAX_MCP_OUTPUT_TOKENS", "12000")
         if self.use_api_billing is not True:
@@ -1660,6 +2194,11 @@ def new_state(self, prompt: str, resume: ResumeToken | None) -> ClaudeStreamStat
         state = ClaudeStreamState()
         state.auto_approve_exit_plan_mode = self._effective_permission_mode() == "auto"
         state.resumed = resume is not None
+        # #289 capture the first user message so loop observers can fall back
+        # to it when ScheduleWakeup uses the <<autonomous-loop-dynamic>>
+        # sentinel.  For resumed runs this is the resume prompt (still better
+        # than letting the sentinel reach Claude verbatim).
+        state.first_user_message_text = prompt
         # #365 propagate MCP catalog observability knobs from WatchdogSettings.
         # Defaults on the dataclass already mirror WatchdogSettings defaults,
         # so a load failure is a safe no-op.
@@ -1952,6 +2491,116 @@ async def _drain_catalog_refresh(
                 )
         state.pending_catalog_refresh_ids.clear()
 
+    async def _post_result_idle_watchdog(
+        self,
+        state: ClaudeStreamState,
+        this_proc_stdin: Any,
+        reader_done: anyio.Event,
+        run_logger: Any,
+        timeout_s: float,
+    ) -> None:
+        """Close stdin once the bidirectional CLI has been idle past the result.
+
+        After ``StreamResultMessage`` the Claude CLI stays alive in the
+        bidirectional/permission-mode protocol so multi-turn sessions don't
+        re-spawn. In practice (#333) this leaves a 400 MB RSS subprocess
+        plus ~200 TCP sockets idling for 30+ minutes between user prompts.
+
+        Mechanism: poll ``state.result_received_at``. When elapsed exceeds
+        ``timeout_s`` and no approval-state references the session, close
+        ``this_proc_stdin`` (same call as the normal-flow exit on line
+        2412). The CLI hits stdin EOF and exits gracefully (rc=0). The
+        auto-continue safety gate excludes ``last_event_type == "result"``
+        so the clean exit will not phantom-resume the session
+        (test_skips_result_event_type in test_exec_bridge.py locks this).
+
+        Approval-state guard: ``_REQUEST_TO_SESSION`` and
+        ``_PENDING_ASK_REQUESTS`` track in-flight callback responses. If
+        either has live entries for this session we re-arm the timer
+        rather than orphaning a button-click control_response that's
+        mid-flight.
+        """
+        # Poll often enough to react within a few seconds of the deadline,
+        # but not so often that we burn CPU on a fully idle session.
+        poll_interval = max(5.0, min(timeout_s / 20.0, 30.0))
+        while not reader_done.is_set():
+            await anyio.sleep(poll_interval)
+            if reader_done.is_set():
+                return
+            armed_at = state.result_received_at
+            if armed_at is None:
+                continue
+            elapsed = time.monotonic() - armed_at
+
+            # #507: dead-ScheduleWakeup shortcut. ScheduleWakeup outside
+            # ``/loop dynamic mode`` is a silent no-op upstream — the
+            # wakeup never fires, the agent's turn ended, and we'd otherwise
+            # wait the full ``timeout_s`` (default 600 s) before closing
+            # stdin. Detect the case via the live_wakeups registry and the
+            # /loop master toggle for this chat; cut the effective timeout
+            # to ``max_armed_delay + 60s grace`` so the session closes
+            # within ~delay+grace instead of 10 minutes.
+            effective_timeout = timeout_s
+            dead_wakeup = False
+            if state.live_wakeups_arm_delay:
+                from ..utils.paths import get_run_channel_id
+
+                _chat_id = get_run_channel_id()
+                if _chat_id is not None and not _loop_enabled_for_chat(_chat_id):
+                    _max_delay = max(state.live_wakeups_arm_delay.values(), default=0.0)
+                    effective_timeout = min(timeout_s, _max_delay + 60.0)
+                    dead_wakeup = True
+            if elapsed < effective_timeout:
+                continue
+
+            # Locate the session id for the approval-state guard. The
+            # Claude factory's resume token is set during the very first
+            # StartedEvent, so by the time a result lands we always have
+            # one — but defend against the rare race where the watchdog
+            # ticks before that first started event.
+            sid = (
+                state.factory.resume.value if state.factory.resume is not None else None
+            )
+            pending_requests = (
+                [k for k, v in _REQUEST_TO_SESSION.items() if v == sid] if sid else []
+            )
+            pending_asks = (
+                [k for k in _PENDING_ASK_REQUESTS if _REQUEST_TO_SESSION.get(k) == sid]
+                if sid
+                else []
+            )
+            if pending_requests or pending_asks:
+                run_logger.info(
+                    "claude.post_result_idle.deferred",
+                    session_id=sid,
+                    pending_requests=len(pending_requests),
+                    pending_asks=len(pending_asks),
+                    elapsed_s=round(elapsed, 1),
+                    timeout_s=timeout_s,
+                )
+                # Re-arm: push the deadline forward by one full interval.
+                state.result_received_at = time.monotonic()
+                continue
+
+            run_logger.info(
+                "claude.post_result_idle.closing_stdin",
+                session_id=sid,
+                elapsed_s=round(elapsed, 1),
+                timeout_s=timeout_s,
+                effective_timeout_s=round(effective_timeout, 1),
+                dead_wakeup=dead_wakeup,
+            )
+            # #470: stamp closed-at signals BEFORE the actual stdin close
+            # so the bridge's heartbeat tick (which polls engine_state via
+            # duck-typing) can fire the one-shot closing Telegram message.
+            # ``post_result_closing_sent`` stays False — the bridge sets
+            # it after the message is sent (idempotency).
+            state.post_result_closed_at = time.monotonic()
+            state.post_result_idle_minutes = elapsed / 60.0
+            with contextlib.suppress(Exception):
+                await this_proc_stdin.aclose()
+            return
+
     def translate(
         self,
         data: claude_schema.StreamJsonMessage,
@@ -2089,12 +2738,33 @@ async def run_impl(
         if env is not None:
             cmd = wrap_with_env_i(cmd, env)
             env = None
+        # #205 / #478: redact two flavours of secret material before logging
+        # ``args`` at INFO:
+        #   1. ``env -i KEY=VAL`` pairs from wrap_with_env_i embed live
+        #      credentials (bot tokens, API keys, BWS access token, ...)
+        #      — handled by ``redact_env_i_args`` (#361).
+        #   2. In legacy mode ``build_args`` ends with ``-- <prompt>`` so the
+        #      whole prompt sits as the last argv element. Truncate at the
+        #      ``--`` boundary so prompt content never reaches INFO logs.
+        logged_args = redact_env_i_args(cmd)[1:]
+        if "--" in logged_args:
+            sep = logged_args.index("--")
+            logged_args = [*logged_args[:sep], "--", "<prompt redacted>"]
         run_logger.info(
             "runner.start",
             engine=self.engine,
             resume=resume.value if resume else None,
-            prompt=prompt[:100] + "…" if len(prompt) > 100 else prompt,
             prompt_len=len(prompt),
+            args=logged_args,
+        )
+        # #205 / #478: prompt content may carry credentials/PII; keep at DEBUG
+        # so it only surfaces with explicit operator opt-in. Mirrors the
+        # base ``runner.run_impl`` companion log so behaviour is consistent
+        # across all engines.
+        run_logger.debug(
+            "runner.start_prompt",
+            engine=self.engine,
+            prompt_preview=prompt[:100] + "…" if len(prompt) > 100 else prompt,
         )
 
         cwd = get_run_base_dir()
@@ -2193,6 +2863,26 @@ async def run_impl(
                 self.current_stream = stream
                 reader_done = anyio.Event()
 
+                # #333: load post-result idle settings before the task group
+                # so the watchdog gets a snapshot. A load failure leaves the
+                # legacy "stay alive forever" behaviour in place.
+                post_result_idle_enabled = True
+                post_result_idle_timeout_s = 600.0
+                try:
+                    result = load_settings_if_exists()
+                    if result is not None:
+                        settings_obj, _ = result
+                        post_result_idle_enabled = (
+                            settings_obj.watchdog.post_result_idle_enabled
+                        )
+                        post_result_idle_timeout_s = float(
+                            settings_obj.watchdog.post_result_idle_timeout
+                        )
+                except Exception:  # noqa: BLE001 — settings errors must not block a run
+                    run_logger.debug(
+                        "post_result_idle.settings_load_failed", exc_info=True
+                    )
+
                 async with anyio.create_task_group() as tg:
                     tg.start_soon(
                         drain_stderr,
@@ -2209,6 +2899,19 @@ async def run_impl(
                         run_logger,
                         proc.pid,
                     )
+                    if (
+                        use_control_channel
+                        and this_proc_stdin is not None
+                        and post_result_idle_enabled
+                    ):
+                        tg.start_soon(
+                            self._post_result_idle_watchdog,
+                            state,
+                            this_proc_stdin,
+                            reader_done,
+                            run_logger,
+                            post_result_idle_timeout_s,
+                        )
                     async for evt in self._iter_jsonl_events(
                         stdout=proc.stdout,
                         stream=stream,
@@ -2227,6 +2930,13 @@ async def run_impl(
                     if use_control_channel and this_proc_stdin is not None:
                         with contextlib.suppress(Exception):
                             await this_proc_stdin.aclose()
+                    # #502 — Close our read end of stderr so drain_stderr
+                    # exits even when a child (e.g. an MCP server) inherited
+                    # the stderr fd and is keeping it open. Without this the
+                    # task group blocks forever waiting on drain_stderr and
+                    # `proc.wait()` below is never reached.
+                    with contextlib.suppress(Exception):
+                        await proc.stderr.aclose()
 
                 rc = await proc.wait()
                 run_logger.info("subprocess.exit", pid=proc.pid, rc=rc)
@@ -2309,7 +3019,7 @@ async def run_impl(
             self._pty_master_fd = None
 
 
-def build_runner(config: EngineConfig, _config_path: Path) -> Runner:
+def build_runner(config: EngineConfig, config_path: Path) -> Runner:
     claude_cmd = shutil.which("claude") or "claude"
 
     model = config.get("model")
@@ -2322,11 +3032,41 @@ def build_runner(config: EngineConfig, _config_path: Path) -> Runner:
     permission_mode = config.get("permission_mode")
     title = str(model) if model is not None else "claude"
 
+    extra_args_value = config.get("extra_args")
+    if extra_args_value is None:
+        extra_args: list[str] = []
+    elif isinstance(extra_args_value, list) and all(
+        isinstance(item, str) for item in extra_args_value
+    ):
+        extra_args = list(extra_args_value)
+    else:
+        logger.warning(
+            "claude.config.invalid",
+            error="extra_args must be a list of strings",
+            config_path=str(config_path),
+        )
+        raise ConfigError(
+            f"Invalid `claude.extra_args` in {config_path}; expected a list of strings."
+        )
+
+    reserved_flag = _find_reserved_flag(extra_args)
+    if reserved_flag:
+        logger.warning(
+            "claude.config.invalid",
+            error=f"reserved flag {reserved_flag!r} is managed by Untether",
+            config_path=str(config_path),
+        )
+        raise ConfigError(
+            f"Invalid `claude.extra_args` in {config_path}; flag {reserved_flag!r} "
+            f"is managed by Untether and cannot be overridden."
+        )
+
     return ClaudeRunner(
         claude_cmd=claude_cmd,
         model=model,
         permission_mode=permission_mode,
         allowed_tools=allowed_tools,
+        extra_args=extra_args,
         dangerously_skip_permissions=dangerously_skip_permissions,
         use_api_billing=use_api_billing,
         session_title=title,
diff --git a/src/untether/runners/gemini.py b/src/untether/runners/gemini.py
index 888f36e6..b8b54c8e 100644
--- a/src/untether/runners/gemini.py
+++ b/src/untether/runners/gemini.py
@@ -317,6 +317,13 @@ class GeminiRunner(ResumeTokenMixin, JsonlSubprocessRunner):
     gemini_cmd: str = "gemini"
     model: str | None = None
     session_title: str = "gemini"
+    # #471: Gemini CLI rejects runs from any directory not present in
+    # ~/.gemini/trustedFolders.json — even with --approval-mode yolo. Untether
+    # is always headless so there is no way to interactively trust a folder;
+    # we pass --skip-trust by default for the same reason we pass yolo. Set
+    # `[gemini] skip_trust = false` in untether.toml to opt out (e.g. if the
+    # operator wants Gemini's project-local extension/MCP trust gate enforced).
+    skip_trust: bool = True
     logger = logger
 
     def format_resume(self, token: ResumeToken) -> str:
@@ -351,6 +358,8 @@ def build_args(
             args.extend(["--approval-mode", run_options.permission_mode])
         else:
             args.extend(["--approval-mode", "yolo"])
+        if self.skip_trust:
+            args.append("--skip-trust")
         args.append(f"--prompt={self.sanitize_prompt(prompt)}")
         return args
 
@@ -538,11 +547,23 @@ def build_runner(config: EngineConfig, config_path: Path) -> Runner:
             f"Invalid `gemini.model` in {config_path}; expected a string."
         )
 
+    skip_trust_value = config.get("skip_trust", True)
+    if not isinstance(skip_trust_value, bool):
+        logger.warning(
+            "gemini.config.invalid",
+            error="skip_trust must be a boolean",
+            config_path=str(config_path),
+        )
+        raise ConfigError(
+            f"Invalid `gemini.skip_trust` in {config_path}; expected a boolean."
+        )
+
     title = str(model) if model is not None else "gemini"
 
     return GeminiRunner(
         model=model,
         session_title=title,
+        skip_trust=skip_trust_value,
     )
 
 
diff --git a/src/untether/runners/pi.py b/src/untether/runners/pi.py
index 131f7a33..6e00e383 100644
--- a/src/untether/runners/pi.py
+++ b/src/untether/runners/pi.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import contextlib
 import os
 import re
 from collections.abc import AsyncIterator
@@ -48,6 +49,28 @@
 _SESSION_ID_PREFIX_LEN = 8
 
 
+def _load_env_extras() -> tuple[tuple[str, ...], tuple[str, ...]]:
+    """#409: read [security] env_extra_allow / env_extra_prefix_allow.
+
+    Best-effort — config errors must never block a run, so we swallow
+    them and fall back to the built-in defaults. Returns
+    ``(extra_exact, extra_prefix)``.
+    """
+    from ..settings import load_settings_if_exists
+
+    try:
+        result = load_settings_if_exists()
+        if result is None:
+            return ((), ())
+        settings, _ = result
+        return (
+            tuple(settings.security.env_extra_allow),
+            tuple(settings.security.env_extra_prefix_allow),
+        )
+    except Exception:  # noqa: BLE001 — never let config errors block a run
+        return ((), ())
+
+
 @dataclass(slots=True)
 class PiStreamState:
     resume: ResumeToken
@@ -455,10 +478,13 @@ def stdin_payload(
     def env(self, *, state: PiStreamState) -> dict[str, str] | None:
         # #198: allowlist filter — Pi subprocess no longer inherits the
         # parent's full environment. See `utils/env_policy.py` for the
-        # canonical list + extension notes.
-        from ..utils.env_policy import filtered_env
+        # canonical list + extension notes. #409: thread per-deployment
+        # extras from [security] env_extra_allow / env_extra_prefix_allow.
+        from ..utils.env_policy import filtered_env, log_user_extensions_once
 
-        env = filtered_env()
+        extra_exact, extra_prefix = _load_env_extras()
+        log_user_extensions_once(extra_exact, extra_prefix)
+        env = filtered_env(extra_allow=extra_exact, extra_prefix=extra_prefix)
         env.setdefault("NO_COLOR", "1")
         env.setdefault("CI", "1")
         return env
@@ -586,7 +612,12 @@ def stream_end_events(
     def _new_session_path(self) -> str:
         cwd = get_run_base_dir() or Path.cwd()
         session_dir = _default_session_dir(cwd)
-        session_dir.mkdir(parents=True, exist_ok=True)
+        # #207: 0o700 keeps Pi session JSONL out of reach of other users on
+        # shared hosts. mkdir's mode arg is ignored for existing dirs, so
+        # chmod the directory after to also tighten any pre-existing one.
+        session_dir.mkdir(parents=True, exist_ok=True, mode=0o700)
+        with contextlib.suppress(OSError):
+            session_dir.chmod(0o700)
         timestamp = datetime.now(UTC).isoformat()
         safe_timestamp = timestamp.replace(":", "-").replace(".", "-")
         token = uuid4().hex
diff --git a/src/untether/runners/run_options.py b/src/untether/runners/run_options.py
index 01d43a2c..3e89c46b 100644
--- a/src/untether/runners/run_options.py
+++ b/src/untether/runners/run_options.py
@@ -18,6 +18,10 @@ class EngineRunOptions:
     show_resume_line: bool | None = None
     budget_enabled: bool | None = None
     budget_auto_cancel: bool | None = None
+    # #289 — per-chat /loop and ScheduleWakeup observation toggle.  ``None``
+    # means "follow global ``[loop] enabled``"; True/False is an explicit
+    # per-chat override set via ``/config → 🔁 Loop mode``.
+    loop_enabled: bool | None = None
 
 
 # Canonical per-engine permission_mode value sets. Used by trigger config
diff --git a/src/untether/schemas/claude.py b/src/untether/schemas/claude.py
index 868284e1..e16f0b96 100644
--- a/src/untether/schemas/claude.py
+++ b/src/untether/schemas/claude.py
@@ -32,12 +32,49 @@ class StreamToolResultBlock(
     msgspec.Struct, tag="tool_result", tag_field="type", forbid_unknown_fields=False
 ):
     tool_use_id: str
-    content: str | list[dict[str, Any]] | None = None
+    # #501 — Claude Code may emit `content` as a single content block
+    # object (e.g. {"type": "text", "text": "..."}) in addition to the
+    # documented str / list[dict] / null shapes. _normalize_tool_result
+    # already handles dict; the schema must accept it too or msgspec
+    # raises ValidationError and the line is silently dropped.
+    content: str | dict[str, Any] | list[dict[str, Any]] | None = None
+    is_error: bool | None = None
+
+
+# #489 — Anthropic server-side tools (web_search, code_execution, computer_use, …)
+# emit `server_tool_use` content blocks. Structurally identical to `tool_use`.
+class StreamServerToolUseBlock(
+    msgspec.Struct,
+    tag="server_tool_use",
+    tag_field="type",
+    forbid_unknown_fields=False,
+):
+    id: str
+    name: str
+    input: dict[str, Any]
+
+
+# #489 — Result of the parent agent's `advisor()` meta-tool. Structurally identical
+# to `tool_result`.
+class StreamAdvisorToolResultBlock(
+    msgspec.Struct,
+    tag="advisor_tool_result",
+    tag_field="type",
+    forbid_unknown_fields=False,
+):
+    tool_use_id: str
+    # #501 — see StreamToolResultBlock.content note.
+    content: str | dict[str, Any] | list[dict[str, Any]] | None = None
     is_error: bool | None = None
 
 
 type StreamContentBlock = (
-    StreamTextBlock | StreamThinkingBlock | StreamToolUseBlock | StreamToolResultBlock
+    StreamTextBlock
+    | StreamThinkingBlock
+    | StreamToolUseBlock
+    | StreamToolResultBlock
+    | StreamServerToolUseBlock
+    | StreamAdvisorToolResultBlock
 )
 
 
diff --git a/src/untether/session_stats.py b/src/untether/session_stats.py
index caf89387..08acdc25 100644
--- a/src/untether/session_stats.py
+++ b/src/untether/session_stats.py
@@ -22,12 +22,21 @@ class DayBucket:
     action_count: int = 0
     duration_ms: int = 0
     last_run_ts: float = 0.0
+    # #271 Tier 3: split runs by provenance for the /stats breakdown.
+    triggered_count: int = 0
+    manual_count: int = 0
 
-    def record(self, actions: int, duration_ms: int) -> None:
+    def record(
+        self, actions: int, duration_ms: int, *, triggered: bool = False
+    ) -> None:
         self.run_count += 1
         self.action_count += actions
         self.duration_ms += duration_ms
         self.last_run_ts = time.time()
+        if triggered:
+            self.triggered_count += 1
+        else:
+            self.manual_count += 1
 
     def to_dict(self) -> dict:
         return {
@@ -35,6 +44,8 @@ def to_dict(self) -> dict:
             "action_count": self.action_count,
             "duration_ms": self.duration_ms,
             "last_run_ts": self.last_run_ts,
+            "triggered_count": self.triggered_count,
+            "manual_count": self.manual_count,
         }
 
     @classmethod
@@ -44,6 +55,8 @@ def from_dict(cls, data: dict) -> DayBucket:
             action_count=data.get("action_count", 0),
             duration_ms=data.get("duration_ms", 0),
             last_run_ts=data.get("last_run_ts", 0.0),
+            triggered_count=data.get("triggered_count", 0),
+            manual_count=data.get("manual_count", 0),
         )
 
 
@@ -54,6 +67,8 @@ class AggregatedStats:
     action_count: int = 0
     duration_ms: int = 0
     last_run_ts: float = 0.0
+    triggered_count: int = 0
+    manual_count: int = 0
 
 
 @dataclass
@@ -86,12 +101,19 @@ def _load(self) -> None:
     def _save(self) -> None:
         atomic_write_json(self.path, self._data)
 
-    def record_run(self, engine: str, actions: int, duration_ms: int) -> None:
+    def record_run(
+        self,
+        engine: str,
+        actions: int,
+        duration_ms: int,
+        *,
+        triggered: bool = False,
+    ) -> None:
         today = time.strftime("%Y-%m-%d")
         engines = self._data.setdefault("engines", {})
         engine_days = engines.setdefault(engine, {})
         bucket = DayBucket.from_dict(engine_days.get(today, {}))
-        bucket.record(actions, duration_ms)
+        bucket.record(actions, duration_ms, triggered=triggered)
         engine_days[today] = bucket.to_dict()
         self._save()
 
@@ -116,6 +138,8 @@ def aggregate(
             total_actions = 0
             total_duration = 0
             last_ts = 0.0
+            total_triggered = 0
+            total_manual = 0
 
             for date_str, bucket_data in days.items():
                 if period == "today" and date_str != today:
@@ -139,6 +163,8 @@ def aggregate(
                 total_actions += bucket.action_count
                 total_duration += bucket.duration_ms
                 last_ts = max(last_ts, bucket.last_run_ts)
+                total_triggered += bucket.triggered_count
+                total_manual += bucket.manual_count
 
             if total_runs > 0:
                 results.append(
@@ -148,6 +174,8 @@ def aggregate(
                         action_count=total_actions,
                         duration_ms=total_duration,
                         last_run_ts=last_ts,
+                        triggered_count=total_triggered,
+                        manual_count=total_manual,
                     )
                 )
 
@@ -182,10 +210,16 @@ def init_stats(config_path: Path) -> None:
     _store = SessionStatsStore(stats_path)
 
 
-def record_run(engine: str, actions: int, duration_ms: int) -> None:
+def record_run(
+    engine: str,
+    actions: int,
+    duration_ms: int,
+    *,
+    triggered: bool = False,
+) -> None:
     """Record a completed run. No-op if store not initialised."""
     if _store is not None:
-        _store.record_run(engine, actions, duration_ms)
+        _store.record_run(engine, actions, duration_ms, triggered=triggered)
 
 
 def get_stats(
diff --git a/src/untether/settings.py b/src/untether/settings.py
index 47675410..96bc66db 100644
--- a/src/untether/settings.py
+++ b/src/untether/settings.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import os
+import re
 from collections.abc import Iterable
 from pathlib import Path
 from typing import Annotated, Any, ClassVar, Literal
@@ -116,12 +117,21 @@ class TelegramTransportSettings(BaseModel):
     bot_token: SecretStr
     chat_id: StrictInt
     allowed_user_ids: list[StrictInt] = Field(default_factory=list)
+    # #377: opt-in escape hatch for demos/dev. When the allowlist is
+    # empty AND this flag is False, startup fails with a ConfigError so
+    # accidentally-public bots can't slip into production. Setting this
+    # to True is logged at INFO on every boot so the deviation is
+    # visible in journalctl.
+    allow_any_user: bool = False
     message_overflow: Literal["trim", "split"] = "split"
     voice_transcription: bool = False
     voice_max_bytes: StrictInt = 10 * 1024 * 1024
     voice_transcription_model: NonEmptyStr = "gpt-4o-mini-transcribe"
     voice_transcription_base_url: NonEmptyStr | None = None
-    voice_transcription_api_key: NonEmptyStr | None = None
+    # #378: SecretStr (parity with bot_token from #196) — masks repr()/str()/
+    # tracebacks/structlog. Access the raw value via .get_secret_value() at the
+    # transport boundary (telegram/loop.py before passing to OpenAI SDK).
+    voice_transcription_api_key: SecretStr | None = None
     voice_show_transcription: bool = True
     session_mode: Literal["stateless", "chat"] = "stateless"
     show_resume_line: bool = True
@@ -143,6 +153,42 @@ def _validate_bot_token_not_empty(cls, v: SecretStr) -> SecretStr:
             raise ValueError("bot_token must not be empty")
         return SecretStr(token)
 
+    @field_validator("voice_transcription_api_key", mode="after")
+    @classmethod
+    def _validate_voice_key_not_empty(cls, v: SecretStr | None) -> SecretStr | None:
+        """#378: preserve the pre-SecretStr `NonEmptyStr | None` contract.
+        Empty / whitespace-only strings round-trip to None so downstream code
+        can use a simple `is not None` (or truthy) check at the call site."""
+        if v is None:
+            return None
+        key = v.get_secret_value().strip()
+        if not key:
+            return None
+        return SecretStr(key)
+
+    @model_validator(mode="after")
+    def _validate_allowed_user_ids_or_optin(self) -> TelegramTransportSettings:
+        """#377: refuse to start with no user allowlist unless the operator
+        explicitly opts out.
+
+        ``allowed_user_ids = []`` previously degraded to "any Telegram user
+        who knows the bot username can send commands" with only a runtime
+        warning. That's an insecure default — it shipped real production
+        bots that were silently public. The fix promotes the warning to a
+        hard ConfigError at config-load time. Operators who actually want
+        an open bot (demos, hackathons, dev) opt in by setting
+        ``allow_any_user = true``.
+        """
+        if not self.allowed_user_ids and not self.allow_any_user:
+            raise ValueError(
+                "[transports.telegram] allowed_user_ids is empty — bot would "
+                "accept commands from anyone who knows its username. Set a "
+                "non-empty list of Telegram user IDs, or pass "
+                "`allow_any_user = true` to opt in to an open bot (dev/demo "
+                "only)."
+            )
+        return self
+
 
 class TransportsSettings(BaseModel):
     telegram: TelegramTransportSettings
@@ -176,6 +222,28 @@ class CostBudgetSettings(BaseModel):
     auto_cancel: bool = False
 
 
+class LoopSettings(BaseModel):
+    """Untether-side observation of Claude Code's session-scoped scheduling
+    tools (CronCreate, ScheduleWakeup) so /loop and dynamic-mode wakeups
+    keep firing after the subprocess exits.  Off by default — opt-in
+    per-chat via /config → 🔁 Loop mode (#289).
+
+    Cost limits are NOT in [loop]; they live in [cost_budget] and apply
+    to loop fires automatically.  The caps below are runaway-safety
+    only.
+    """
+
+    model_config = ConfigDict(extra="forbid", str_strip_whitespace=True)
+
+    enabled: bool = False
+    inline_threshold_seconds: int = Field(default=300, ge=0)
+    redundancy_check_interval: int = Field(default=30, ge=1)
+    max_iterations: int = Field(default=20, ge=1, le=10000)
+    max_total_duration_hours: int = Field(default=4, ge=1, le=168)
+    min_interval_seconds: int = Field(default=60, ge=60)
+    expiry_days: int = Field(default=7, ge=1, le=30)
+
+
 class FooterSettings(BaseModel):
     model_config = ConfigDict(extra="forbid", str_strip_whitespace=True)
 
@@ -243,6 +311,41 @@ class WatchdogSettings(BaseModel):
     prespawn_ram_warn_mb: int = Field(default=2000, ge=0, le=65536)
     prespawn_ram_block_mb: int = Field(default=500, ge=0, le=65536)
 
+    # #438: user-configurable Claude SSE-stream watchdog. Sets
+    # ``CLAUDE_STREAM_IDLE_TIMEOUT_MS`` for the Claude subprocess (via
+    # ``setdefault`` — shell-set values still win). Default 300000 ms (5 min)
+    # matches the upstream undici idle-body timeout and #342's reasoning.
+    # Long-form opus 4.7 1M plan-mode generations can legitimately idle the
+    # SSE stream past 5 min; deployments that hit upstream Anthropic API
+    # stalls (#438) can raise this to 600000-900000 to ride out longer
+    # silences before Untether reports the run failed. Range 30s-30min.
+    claude_stream_idle_timeout_ms: int = Field(default=300_000, ge=30_000, le=1_800_000)
+
+    # #333: post-result idle timeout for Claude bidirectional sessions.
+    # Claude Code in stream-json + permission-mode keeps stdin open after
+    # emitting a `result` event so multi-turn sessions don't re-spawn. In
+    # practice this leaves a 400 MB RSS subprocess + ~200 TCP sockets
+    # idling for tens of minutes between user prompts. After
+    # `post_result_idle_timeout` seconds with no new event we close the
+    # subprocess's stdin so the CLI exits gracefully (rc=0). The auto-
+    # continue safety gate already excludes ``last_event_type == "result"``
+    # so the clean exit will not phantom-resume the session. Pause/resume
+    # via Telegram is unaffected — the resume token is preserved on the
+    # progress tracker. Set ``post_result_idle_enabled = false`` to keep
+    # the legacy "stay alive forever" behaviour (e.g. for users who pipe
+    # successive turns within seconds and want to skip the spawn cost).
+    # Range 30s-1h.
+    post_result_idle_enabled: bool = True
+    post_result_idle_timeout: float = Field(default=600.0, ge=30, le=3600)
+
+    # #481: grace window for fresh Bash/BashOutput tool calls. When the most
+    # recent action is Bash/BashOutput/KillShell and its age is less than
+    # bash_grace_seconds, ProgressEdits._stall_monitor suppresses the Telegram
+    # stall warning (the command may still be in its startup phase / first
+    # poll cycle). Range 5s-300s. Logged as
+    # ``progress_edits.stall_bash_grace_suppressed`` per suppression.
+    bash_grace_seconds: float = Field(default=60.0, ge=5, le=300)
+
     @model_validator(mode="after")
     def _validate_prespawn_ram_ordering(self) -> WatchdogSettings:
         # When both tiers are active, warn must sit above block — otherwise
@@ -267,20 +370,67 @@ class ProgressSettings(BaseModel):
     max_actions: int = Field(default=5, ge=0, le=50)
     min_render_interval: float = Field(default=2.0, ge=0, le=30)
     group_chat_rps: float = Field(default=20.0 / 60.0, gt=0, le=10)
+    # #481: heartbeat tick cadence for the long-running-action elapsed-time
+    # tail and the post-result closing-message poller. Distinct from the
+    # stall-monitor cadence (60s) because lowering that would silently
+    # break stall_repeat_seconds=180 ≈ 3-tick math and the wider stall test
+    # corpus. The stall monitor's loop sleeps min(heartbeat_interval,
+    # stall_check_interval) and only runs the threshold check at the slower
+    # cadence. Range 5s-120s.
+    heartbeat_interval: float = Field(default=30.0, ge=5, le=120)
+
+
+_ENV_NAME_RE = re.compile(r"^[A-Z_][A-Z0-9_]*$")
 
 
 class SecuritySettings(BaseModel):
-    """Runtime security knobs (#361).
+    """Runtime security knobs (#361, #409).
 
     ``env_audit`` enables a one-shot ``/proc/<pid>/environ`` sample on
     Claude session start. Disallowed names emit a structured warning so
     the operator can see when host env leaks past
     :func:`utils.env_policy.filtered_env`.
+
+    ``env_extra_allow`` / ``env_extra_prefix_allow`` (#409) extend the
+    built-in subprocess-env allowlist with per-deployment names so users
+    can thread credential-manager tokens (1Password, Doppler, Vault,
+    Infisical, …) without forking ``utils/env_policy.py``.
     """
 
     model_config = ConfigDict(extra="forbid", str_strip_whitespace=True)
 
     env_audit: bool = True
+    # #409: user-extensible engine-subprocess env allowlist. Each entry
+    # must look like a POSIX env var name (uppercase, digits, underscore;
+    # must not start with a digit). Empty/whitespace strings are rejected
+    # so a stray TOML edit doesn't silently widen the allowlist.
+    env_extra_allow: list[str] = Field(default_factory=list)
+    env_extra_prefix_allow: list[str] = Field(default_factory=list)
+
+    @field_validator("env_extra_allow", "env_extra_prefix_allow", mode="after")
+    @classmethod
+    def _validate_env_names(cls, v: list[str]) -> list[str]:
+        """Each entry must look like a POSIX env-var name.
+
+        Trailing wildcards / glob chars are NOT supported — prefix matches
+        already cover families (``VAULT_*`` is configured as ``"VAULT_"``).
+        """
+        cleaned: list[str] = []
+        for entry in v:
+            if not isinstance(entry, str):
+                raise ValueError(
+                    f"env allowlist entries must be strings (got {type(entry).__name__})"
+                )
+            stripped = entry.strip()
+            if not stripped:
+                raise ValueError("env allowlist entries must not be empty")
+            if not _ENV_NAME_RE.match(stripped):
+                raise ValueError(
+                    f"invalid env name {entry!r} — must match [A-Z_][A-Z0-9_]* "
+                    "(uppercase letters, digits, underscores; cannot start with a digit)"
+                )
+            cleaned.append(stripped)
+        return cleaned
 
 
 class UntetherSettings(BaseSettings):
@@ -301,6 +451,7 @@ class UntetherSettings(BaseSettings):
 
     plugins: PluginsSettings = Field(default_factory=PluginsSettings)
     cost_budget: CostBudgetSettings = Field(default_factory=CostBudgetSettings)
+    loop: LoopSettings = Field(default_factory=LoopSettings)
     footer: FooterSettings = Field(default_factory=FooterSettings)
     preamble: PreambleSettings = Field(default_factory=PreambleSettings)
     progress: ProgressSettings = Field(default_factory=ProgressSettings)
@@ -556,7 +707,10 @@ def _load_settings_from_path(cfg_path: Path) -> UntetherSettings:
     )
     try:
         settings = Bound()
-        logger.info("config.loaded", path=str(cfg_path))
+        # #498 — fires per-helper load (footer/watchdog/progress/auto_continue/
+        # preamble/budget) by design (#269 hot-reload); too noisy at INFO.
+        # See v0.35.4 issue for caching settings within handle_message.
+        logger.debug("config.loaded", path=str(cfg_path))
         return settings
     except ValidationError as exc:
         raise ConfigError(f"Invalid config in {cfg_path}: {exc}") from exc
diff --git a/src/untether/telegram/at_scheduler.py b/src/untether/telegram/at_scheduler.py
index c15ad6d3..4d582419 100644
--- a/src/untether/telegram/at_scheduler.py
+++ b/src/untether/telegram/at_scheduler.py
@@ -16,7 +16,7 @@
 import secrets
 import time
 from collections.abc import Awaitable, Callable
-from dataclasses import dataclass, field
+from dataclasses import dataclass, field, replace
 
 import anyio
 from anyio.abc import TaskGroup
@@ -148,6 +148,16 @@ def schedule_delayed_run(
     token = secrets.token_hex(6)
     now = time.monotonic()
     scope = anyio.CancelScope()
+    # #271 follow-up: stamp trigger_source = "at:<token>" so the run footer
+    # shows provenance (`⏰ at:<token>`) just like cron/webhook fires. Mirrors
+    # TriggerDispatcher's freeze-at-dispatch pattern. If the chat had no
+    # project mapping, create a fresh RunContext carrying just the source so
+    # the runner_bridge meta seed still fires.
+    trigger_source = f"at:{token}"
+    if context is None:
+        context = RunContext(trigger_source=trigger_source)
+    else:
+        context = replace(context, trigger_source=trigger_source)
     entry = _PendingAt(
         token=token,
         chat_id=chat_id,
diff --git a/src/untether/telegram/backend.py b/src/untether/telegram/backend.py
index 4561d79c..a9475dc7 100644
--- a/src/untether/telegram/backend.py
+++ b/src/untether/telegram/backend.py
@@ -286,6 +286,7 @@ async def _send_file_via_bot(
             forward_coalesce_s=settings.forward_coalesce_s,
             media_group_debounce_s=settings.media_group_debounce_s,
             allowed_user_ids=tuple(settings.allowed_user_ids),
+            allow_any_user=settings.allow_any_user,
             topics=settings.topics,
             files=settings.files,
             trigger_config=trigger_config,
diff --git a/src/untether/telegram/bridge.py b/src/untether/telegram/bridge.py
index 561cfdc6..dfdd7d23 100644
--- a/src/untether/telegram/bridge.py
+++ b/src/untether/telegram/bridge.py
@@ -4,6 +4,8 @@
 from dataclasses import dataclass, field
 from typing import TYPE_CHECKING, Literal, cast
 
+from pydantic import SecretStr
+
 from ..context import RunContext
 from ..logging import get_logger
 from ..markdown import MarkdownFormatter, MarkdownParts
@@ -56,15 +58,26 @@ def __init__(
         self._formatter = formatter or MarkdownFormatter()
         self._message_overflow = message_overflow
 
+    def refresh_progress_settings(self, progress: object) -> None:
+        """Push a fresh ``ProgressSettings`` snapshot into the formatter (#269).
+
+        Called per-run from the runner bridge so editing ``[progress]``
+        in ``untether.toml`` applies on the next message. Per-chat
+        ``/verbose`` overrides take precedence (they construct an
+        override formatter on demand from the refreshed defaults).
+        """
+        self._formatter.refresh_from(progress)
+
     def render_progress(
         self,
         state: ProgressState,
         *,
         elapsed_s: float,
         label: str = "working",
+        now: float | None = None,
     ) -> RenderedMessage:
         parts = self._formatter.render_progress_parts(
-            state, elapsed_s=elapsed_s, label=label
+            state, elapsed_s=elapsed_s, label=label, now=now
         )
         text, entities = prepare_telegram(parts)
         if _is_cancelled_label(label):
@@ -159,11 +172,16 @@ class TelegramBridgeConfig:
     voice_max_bytes: int = 10 * 1024 * 1024
     voice_transcription_model: str = "gpt-4o-mini-transcribe"
     voice_transcription_base_url: str | None = None
-    voice_transcription_api_key: str | None = None
+    # #378: SecretStr ferries the key without leaking it through repr/log.
+    voice_transcription_api_key: SecretStr | None = None
     voice_show_transcription: bool = True
     forward_coalesce_s: float = 1.0
     media_group_debounce_s: float = 1.0
     allowed_user_ids: tuple[int, ...] = ()
+    # #377: `allow_any_user=True` is the explicit opt-in for an open bot.
+    # Mirrors `TelegramTransportSettings.allow_any_user` so the loop can
+    # log on every boot (telegram/loop.py:security.allow_any_user).
+    allow_any_user: bool = False
     files: TelegramFilesSettings = field(default_factory=TelegramFilesSettings)
     chat_ids: tuple[int, ...] | None = None
     topics: TelegramTopicsSettings = field(default_factory=TelegramTopicsSettings)
@@ -191,6 +209,7 @@ def update_from(self, settings: TelegramTransportSettings) -> None:
         self.forward_coalesce_s = float(settings.forward_coalesce_s)
         self.media_group_debounce_s = float(settings.media_group_debounce_s)
         self.allowed_user_ids = tuple(settings.allowed_user_ids)
+        self.allow_any_user = bool(settings.allow_any_user)
         self.files = settings.files
 
 
diff --git a/src/untether/telegram/chat_prefs.py b/src/untether/telegram/chat_prefs.py
index cddc228c..114e2839 100644
--- a/src/untether/telegram/chat_prefs.py
+++ b/src/untether/telegram/chat_prefs.py
@@ -18,6 +18,8 @@
 
 class _ChatPrefs(msgspec.Struct, forbid_unknown_fields=False):
     default_engine: str | None = None
+    # #297: storage field name preserved for backward compat with existing
+    # state files. User-facing name is "listen mode" — see listen_mode.py.
     trigger_mode: str | None = None
     context_project: str | None = None
     context_branch: str | None = None
@@ -44,7 +46,7 @@ def _normalize_text(value: str | None) -> str | None:
     return value or None
 
 
-def _normalize_trigger_mode(value: str | None) -> str | None:
+def _normalize_listen_mode(value: str | None) -> str | None:
     if value is None:
         return None
     value = value.strip().lower()
@@ -55,6 +57,10 @@ def _normalize_trigger_mode(value: str | None) -> str | None:
     return None
 
 
+# #297: legacy alias kept so external imports don't break in this release.
+_normalize_trigger_mode = _normalize_listen_mode
+
+
 def _normalize_engine_id(value: str | None) -> str | None:
     if value is None:
         return None
@@ -107,16 +113,16 @@ async def set_default_engine(self, chat_id: ChannelId, engine: str | None) -> No
     async def clear_default_engine(self, chat_id: ChannelId) -> None:
         await self.set_default_engine(chat_id, None)
 
-    async def get_trigger_mode(self, chat_id: ChannelId) -> str | None:
+    async def get_listen_mode(self, chat_id: ChannelId) -> str | None:
         async with self._lock:
             self._reload_locked_if_needed()
             chat = self._get_chat_locked(chat_id)
             if chat is None:
                 return None
-            return _normalize_trigger_mode(chat.trigger_mode)
+            return _normalize_listen_mode(chat.trigger_mode)
 
-    async def set_trigger_mode(self, chat_id: ChannelId, mode: str | None) -> None:
-        normalized = _normalize_trigger_mode(mode)
+    async def set_listen_mode(self, chat_id: ChannelId, mode: str | None) -> None:
+        normalized = _normalize_listen_mode(mode)
         async with self._lock:
             self._reload_locked_if_needed()
             chat = self._get_chat_locked(chat_id)
@@ -127,15 +133,26 @@ async def set_trigger_mode(self, chat_id: ChannelId, mode: str | None) -> None:
                 if self._chat_is_empty(chat):
                     self._remove_chat_locked(chat_id)
                 self._save_locked()
-                logger.info("prefs.trigger.cleared", chat_id=chat_id)
+                logger.info("prefs.listen.cleared", chat_id=chat_id)
                 return
             chat = self._ensure_chat_locked(chat_id)
             chat.trigger_mode = normalized
             self._save_locked()
-            logger.info("prefs.trigger.set", chat_id=chat_id, mode=normalized)
+            logger.info("prefs.listen.set", chat_id=chat_id, mode=normalized)
+
+    async def clear_listen_mode(self, chat_id: ChannelId) -> None:
+        await self.set_listen_mode(chat_id, None)
+
+    # #297: legacy method aliases preserved so any external/uncovered call
+    # site keeps working. Remove after one release cycle (v0.36.x).
+    async def get_trigger_mode(self, chat_id: ChannelId) -> str | None:
+        return await self.get_listen_mode(chat_id)
+
+    async def set_trigger_mode(self, chat_id: ChannelId, mode: str | None) -> None:
+        await self.set_listen_mode(chat_id, mode)
 
     async def clear_trigger_mode(self, chat_id: ChannelId) -> None:
-        await self.set_trigger_mode(chat_id, None)
+        await self.clear_listen_mode(chat_id)
 
     async def get_context(self, chat_id: ChannelId) -> RunContext | None:
         async with self._lock:
@@ -237,7 +254,7 @@ def _ensure_chat_locked(self, chat_id: ChannelId) -> _ChatPrefs:
     def _chat_is_empty(self, chat: _ChatPrefs) -> bool:
         return (
             _normalize_text(chat.default_engine) is None
-            and _normalize_trigger_mode(chat.trigger_mode) is None
+            and _normalize_listen_mode(chat.trigger_mode) is None
             and _normalize_text(chat.context_project) is None
             and _normalize_text(chat.context_branch) is None
             and not self._has_engine_overrides(chat.engine_overrides)
diff --git a/src/untether/telegram/commands/ask_question.py b/src/untether/telegram/commands/ask_question.py
index b59c1933..c815844c 100644
--- a/src/untether/telegram/commands/ask_question.py
+++ b/src/untether/telegram/commands/ask_question.py
@@ -2,9 +2,14 @@
 
 from __future__ import annotations
 
+from typing import TYPE_CHECKING
+
 from ...commands import CommandBackend, CommandContext, CommandResult
 from ...logging import get_logger
-from ...transport import RenderedMessage
+from ...transport import MessageRef, RenderedMessage, SendOptions, Transport
+
+if TYPE_CHECKING:
+    from ...runners.claude import AskQuestionState
 
 logger = get_logger(__name__)
 
@@ -14,6 +19,47 @@
 }
 
 
+async def send_next_ask_question_message(
+    transport: Transport,
+    *,
+    chat_id: int,
+    user_msg_id: int,
+    thread_id: int | None,
+    flow: AskQuestionState,
+    notify: bool = True,
+) -> None:
+    """Send the next question in a multi-question AskUserQuestion flow.
+
+    Used by the text-reply continuation path (after the user clicks "Other"
+    and types an answer). The callback-button path edits the existing message
+    in-place via ``ctx.executor.edit`` instead.
+
+    Regression: prior to #488 the loop dispatcher constructed the
+    ``RenderedMessage`` correctly but passed it to ``send_plain`` which
+    expects a ``str``, causing a ``TypeError`` and crashing the whole
+    Untether process.
+    """
+    from ...runners.claude import format_question_message, get_question_option_buttons
+
+    msg_text = format_question_message(flow)
+    buttons = get_question_option_buttons(flow)
+    await transport.send(
+        channel_id=chat_id,
+        message=RenderedMessage(
+            text=msg_text,
+            extra={
+                "parse_mode": "HTML",
+                "reply_markup": {"inline_keyboard": buttons},
+            },
+        ),
+        options=SendOptions(
+            reply_to=MessageRef(channel_id=chat_id, message_id=user_msg_id),
+            notify=notify,
+            thread_id=thread_id,
+        ),
+    )
+
+
 class AskQuestionCommand:
     """Command backend for AskUserQuestion option selection."""
 
diff --git a/src/untether/telegram/commands/cancel.py b/src/untether/telegram/commands/cancel.py
index d889910c..b801bd9e 100644
--- a/src/untether/telegram/commands/cancel.py
+++ b/src/untether/telegram/commands/cancel.py
@@ -77,6 +77,21 @@ async def handle_cancel(
                 )
             )
             return
+        # Check pending /loop entries for this chat (#289).  Also writes the
+        # do-not-resume sentinel so the upstream session-scoped cron that
+        # may still live in the JSONL transcript can never be re-fired by
+        # us if the user later resumes the session manually.
+        from ... import loop_scheduler
+
+        pending_loops = loop_scheduler.cancel_pending_for_chat(chat_id)
+        if pending_loops:
+            await reply(
+                text=(
+                    f"\u274c cancelled {pending_loops} active loop"
+                    f"{'s' if pending_loops != 1 else ''}."
+                )
+            )
+            return
         logger.debug("cancel.nothing_running", chat_id=chat_id)
         await reply(text="nothing running in this chat.")
         return
diff --git a/src/untether/telegram/commands/config.py b/src/untether/telegram/commands/config.py
index 68aa7ab1..10024582 100644
--- a/src/untether/telegram/commands/config.py
+++ b/src/untether/telegram/commands/config.py
@@ -187,7 +187,7 @@ async def _page_home(ctx: CommandContext) -> None:
     current_engine, engine_label = await _resolve_effective_engine(ctx)
 
     pm_label = "—"
-    trigger_label = "all"
+    listen_label = "all"
     model_label = "default"
     reasoning_label = "default"
     aq_label = "default"
@@ -220,8 +220,8 @@ async def _page_home(ctx: CommandContext) -> None:
             else:
                 pm_label = "read-only"
 
-        trig = await prefs.get_trigger_mode(chat_id)
-        trigger_label = trig or "all"
+        listen = await prefs.get_listen_mode(chat_id)
+        listen_label = listen or "all"
 
         # Model override for current engine
         if engine_override and engine_override.model:
@@ -350,7 +350,25 @@ async def _page_home(ctx: CommandContext) -> None:
         engine_hint = _ENGINE_MODEL_HINTS.get(current_engine, "from CLI settings")
         model_hint = f"  · {engine_hint}"
     lines.append(f"Model: <b>{model_label}</b>{model_hint}")
-    lines.append(f"Trigger: <b>{trigger_label}</b>{_home_hint('tr', trigger_label)}")
+    lines.append(f"Listen: <b>{listen_label}</b>{_home_hint('tr', listen_label)}")
+    # #294: master trigger pause indicator on the home page when there's a
+    # trigger manager with configured crons/webhooks. Sits below the chat
+    # "Listen" line to keep the two senses of "trigger" visually distinct
+    # (cron/webhook system vs the renamed-from-trigger listen mode, #297).
+    triggers_indicator: str | None = None
+    triggers_paused = False
+    triggers_has_any = False
+    if ctx.trigger_manager is not None:
+        triggers_paused = ctx.trigger_manager.is_paused
+        triggers_has_any = (
+            len(ctx.trigger_manager.cron_ids()) > 0
+            or ctx.trigger_manager.webhook_count > 0
+        )
+        if triggers_has_any:
+            state = "⏸ paused" if triggers_paused else "active"
+            triggers_indicator = f"Triggers (cron/webhook): <b>{state}</b>"
+    if triggers_indicator is not None:
+        lines.append(triggers_indicator)
     if show_reasoning:
         home_rs_label = get_reasoning_label(current_engine)
         if reasoning_label == "default":
@@ -396,13 +414,18 @@ async def _page_home(ctx: CommandContext) -> None:
         )
         buttons.append(
             [
-                {"text": "📡 Trigger", "callback_data": "config:tr"},
-                {"text": "⚙️ Engine & model", "callback_data": "config:ag"},
+                {"text": "📡 Listen", "callback_data": "config:tr"},
+                {"text": "🔁 Loop mode", "callback_data": "config:loop"},
             ]
         )
         buttons.append(
             [
                 {"text": f"🧠 {home_rs_label}", "callback_data": "config:rs"},
+                {"text": "⚙️ Engine & model", "callback_data": "config:ag"},
+            ]
+        )
+        buttons.append(
+            [
                 {"text": "ℹ️ About", "callback_data": "config:ab"},
             ]
         )
@@ -420,7 +443,7 @@ async def _page_home(ctx: CommandContext) -> None:
         )
         buttons.append(
             [
-                {"text": "📡 Trigger", "callback_data": "config:tr"},
+                {"text": "📡 Listen", "callback_data": "config:tr"},
                 {"text": "⚙️ Engine & model", "callback_data": "config:ag"},
             ]
         )
@@ -446,7 +469,7 @@ async def _page_home(ctx: CommandContext) -> None:
         )
         buttons.append(
             [
-                {"text": "📡 Trigger", "callback_data": "config:tr"},
+                {"text": "📡 Listen", "callback_data": "config:tr"},
                 {"text": "⚙️ Engine & model", "callback_data": "config:ag"},
             ]
         )
@@ -464,12 +487,24 @@ async def _page_home(ctx: CommandContext) -> None:
                 {"text": "⚙️ Engine & model", "callback_data": "config:ag"},
             ]
         )
-        row3 = [{"text": "📡 Trigger", "callback_data": "config:tr"}]
+        row3 = [{"text": "📡 Listen", "callback_data": "config:tr"}]
         if show_reasoning:
             row3.append({"text": f"🧠 {home_rs_label}", "callback_data": "config:rs"})
         buttons.append(row3)
         buttons.append([{"text": "ℹ️ About", "callback_data": "config:ab"}])
 
+    # #294: master trigger pause toggle row — only when triggers are configured
+    # for this transport. Sits below the per-engine layout so it doesn't
+    # crowd the existing rows. Label reflects current state.
+    if triggers_has_any:
+        if triggers_paused:
+            tg_label = "▶️ Resume triggers"
+            tg_action = "config:tg:resume"
+        else:
+            tg_label = "⏸ Pause triggers"
+            tg_action = "config:tg:pause"
+        buttons.append([{"text": tg_label, "callback_data": tg_action}])
+
     await _respond(ctx, "\n".join(lines), buttons)
 
 
@@ -758,6 +793,137 @@ async def _page_planmode(ctx: CommandContext, action: str | None = None) -> None
     await _respond(ctx, "\n".join(lines), buttons)
 
 
+# ---------------------------------------------------------------------------
+# Loop mode (#289)
+# ---------------------------------------------------------------------------
+
+
+async def _page_loop(ctx: CommandContext, action: str | None = None) -> None:
+    """Loop mode toggle for /loop and ScheduleWakeup observation (#289).
+
+    Mirrors the shape of ``_page_planmode``: tri-state per-chat override
+    (on / off / clear → fall back to global ``[loop] enabled``), explicit
+    cost/quota warning before enabling, deeplink to ``/config:cu`` for
+    setting a budget cap.
+    """
+    from ..chat_prefs import ChatPrefsStore, resolve_prefs_path
+    from ..engine_overrides import LOOP_SUPPORTED_ENGINES, EngineOverrides
+
+    config_path = ctx.config_path
+    if config_path is None:
+        await _respond(
+            ctx,
+            "<b>🔁 Loop mode</b>\n\nUnavailable (no config path).",
+            [[{"text": "← Back", "callback_data": "config:home"}]],
+        )
+        return
+
+    prefs = ChatPrefsStore(resolve_prefs_path(config_path))
+    chat_id = ctx.message.channel_id
+
+    current_engine, _ = await _resolve_effective_engine(ctx)
+    if current_engine not in LOOP_SUPPORTED_ENGINES:
+        await _respond(
+            ctx,
+            (
+                "<b>🔁 Loop mode</b>\n\nOnly available for Claude Code — "
+                "other engines don't have <code>/loop</code> or "
+                "<code>ScheduleWakeup</code>."
+            ),
+            [[{"text": "← Back", "callback_data": "config:home"}]],
+        )
+        return
+
+    engine = current_engine
+
+    # Action handlers
+    if action in {"on", "off", "clr"}:
+        current = await prefs.get_engine_override(chat_id, engine)
+        if action == "on":
+            new_value: bool | None = True
+        elif action == "off":
+            new_value = False
+        else:
+            new_value = None
+        updated = EngineOverrides(
+            model=current.model if current else None,
+            reasoning=current.reasoning if current else None,
+            permission_mode=current.permission_mode if current else None,
+            ask_questions=current.ask_questions if current else None,
+            diff_preview=current.diff_preview if current else None,
+            show_api_cost=current.show_api_cost if current else None,
+            show_subscription_usage=current.show_subscription_usage
+            if current
+            else None,
+            show_resume_line=current.show_resume_line if current else None,
+            budget_enabled=current.budget_enabled if current else None,
+            budget_auto_cancel=current.budget_auto_cancel if current else None,
+            loop_enabled=new_value,
+        )
+        await prefs.set_engine_override(chat_id, engine, updated)
+        logger.info("config.loop.set", chat_id=chat_id, value=new_value)
+        await _page_home(ctx)
+        return
+
+    # Render — resolve current effective state
+    current = await prefs.get_engine_override(chat_id, engine)
+    per_chat = current.loop_enabled if current else None
+    if per_chat is None:
+        try:
+            from ...settings import load_settings_if_exists
+
+            result = load_settings_if_exists()
+            global_enabled = (
+                bool(result[0].loop.enabled) if result is not None else False
+            )
+        except Exception:  # noqa: BLE001
+            global_enabled = False
+        effective = "On (global)" if global_enabled else "Off (global)"
+    elif per_chat:
+        effective = "On (per-chat)"
+    else:
+        effective = "Off (per-chat)"
+
+    body = (
+        f"<b>🔁 Loop mode</b>\n\n"
+        f"Currently: <b>{effective}</b>\n\n"
+        f"When <b>ON</b>:\n"
+        f"  Claude Code can schedule and continue tasks autonomously.\n"
+        f"  <code>/loop 5m check the deploy</code> works end-to-end via "
+        f"Telegram — Untether observes Claude's CronCreate / "
+        f"ScheduleWakeup tool calls and re-fires each iteration when due, "
+        f"spawning a fresh <code>claude --resume</code> per fire.\n\n"
+        f"When <b>OFF</b> (default):\n"
+        f"  Claude Code only runs when you message it. <code>/loop</code> "
+        f"appears to register schedules during a turn, but nothing fires "
+        f"after the subprocess exits.\n\n"
+        f"⚠️ <b>Cost &amp; quota risk when ON</b>\n"
+        f"  Autonomous loops consume API credits or your Claude "
+        f"subscription quota. A 24h <code>/loop 1m</code> can fire up to "
+        f"1440 times. Set a budget in 💰 Cost &amp; usage <i>before</i> "
+        f"turning Loop mode on — the same daily cost cap applies to loop "
+        f"fires automatically."
+    )
+    buttons = [
+        [
+            {
+                "text": _check("On", active=per_chat is True),
+                "callback_data": "config:loop:on",
+            },
+            {
+                "text": _check("Off", active=per_chat is False),
+                "callback_data": "config:loop:off",
+            },
+        ],
+        [
+            {"text": "Clear override", "callback_data": "config:loop:clr"},
+            {"text": "💰 Set a budget", "callback_data": "config:cu"},
+        ],
+        [{"text": "← Back", "callback_data": "config:home"}],
+    ]
+    await _respond(ctx, body, buttons)
+
+
 # ---------------------------------------------------------------------------
 # Verbose
 # ---------------------------------------------------------------------------
@@ -923,7 +1089,8 @@ async def _page_engine(ctx: CommandContext, action: str | None = None) -> None:
 
 
 # ---------------------------------------------------------------------------
-# Trigger mode
+# Listen mode (#297: renamed from "Trigger mode" to disambiguate from
+# webhook/cron triggers. Callback prefix `tr` kept for stable callback_data.)
 # ---------------------------------------------------------------------------
 
 
@@ -934,7 +1101,7 @@ async def _page_trigger(ctx: CommandContext, action: str | None = None) -> None:
     if config_path is None:
         await _respond(
             ctx,
-            "<b>📡 Trigger mode</b>\n\nUnavailable (no config path).",
+            "<b>📡 Listen mode</b>\n\nUnavailable (no config path).",
             [[{"text": "← Back", "callback_data": "config:home"}]],
         )
         return
@@ -943,26 +1110,26 @@ async def _page_trigger(ctx: CommandContext, action: str | None = None) -> None:
     chat_id = ctx.message.channel_id
 
     if action == "all":
-        await prefs.clear_trigger_mode(chat_id)
-        logger.info("config.trigger.set", chat_id=chat_id, mode="all")
+        await prefs.clear_listen_mode(chat_id)
+        logger.info("config.listen.set", chat_id=chat_id, mode="all")
         await _page_home(ctx)
         return
     elif action == "men":
-        await prefs.set_trigger_mode(chat_id, "mentions")
-        logger.info("config.trigger.set", chat_id=chat_id, mode="mentions")
+        await prefs.set_listen_mode(chat_id, "mentions")
+        logger.info("config.listen.set", chat_id=chat_id, mode="mentions")
         await _page_home(ctx)
         return
     elif action == "clr":
-        await prefs.clear_trigger_mode(chat_id)
-        logger.info("config.trigger.cleared", chat_id=chat_id)
+        await prefs.clear_listen_mode(chat_id)
+        logger.info("config.listen.cleared", chat_id=chat_id)
         await _page_home(ctx)
         return
 
-    current = await prefs.get_trigger_mode(chat_id)
+    current = await prefs.get_listen_mode(chat_id)
     current_label = current or "all"
 
     lines = [
-        "<b>📡 Trigger mode</b>",
+        "<b>📡 Listen mode</b>",
         "",
         "Control when the bot responds in group chats.",
         "",
@@ -1810,6 +1977,188 @@ async def _page_about(ctx: CommandContext, action: str | None = None) -> None:
     await _respond(ctx, "\n".join(lines), buttons)
 
 
+# ---------------------------------------------------------------------------
+# Triggers (cron + webhook) master pause toggle (#294) + per-chat detail (#271)
+# ---------------------------------------------------------------------------
+
+
+_TRIGGER_LIST_CAP = 10
+
+
+def _format_trigger_relative(ts: float | None) -> str:
+    """Render a unix timestamp as a relative-time hint for the triggers page.
+
+    Mirrors ``stats._format_last_run`` semantics so /config and /stats agree
+    on phrasing.
+    """
+    import time
+
+    if ts is None or ts <= 0:
+        return "never"
+    diff = time.time() - ts
+    if diff < 60:
+        return "just now"
+    if diff < 3600:
+        return f"{int(diff // 60)}m ago"
+    if diff < 86400:
+        return f"{int(diff // 3600)}h ago"
+    return f"{int(diff // 86400)}d ago"
+
+
+def _truncate_field(value: str | None, limit: int = 24) -> str:
+    if not value:
+        return "—"
+    if len(value) <= limit:
+        return value
+    return value[: limit - 1] + "…"
+
+
+async def _page_triggers(ctx: CommandContext, action: str | None = None) -> None:
+    """Triggers control + per-chat visibility page.
+
+    Lives on its own ``/config`` page distinct from ``/config → 📡 Trigger``
+    (which is the listen-mode all/mentions chat-routing setting). Pause/resume
+    is the master kill-switch (#294). Below the controls, when triggers are
+    configured for the current chat, the page lists each cron and webhook
+    with its schedule/path, project, engine, and last-fired timestamp (#271
+    Tier 2 + Tier 3).
+    """
+    from ...triggers.describe import describe_cron
+    from ...triggers.history import get_last_fired
+
+    mgr = ctx.trigger_manager
+    chat_id = ctx.message.channel_id
+    chat_id_int = chat_id if isinstance(chat_id, int) else None
+
+    if mgr is None:
+        await _respond(
+            ctx,
+            "<b>⏰ Triggers</b>\n\nUnavailable (transport has no trigger support).",
+            [[{"text": "← Back", "callback_data": "config:home"}]],
+        )
+        return
+
+    cron_count = len(mgr.cron_ids())
+    webhook_count = mgr.webhook_count
+    has_any = cron_count > 0 or webhook_count > 0
+
+    if action == "pause" and has_any and mgr.pause():
+        logger.info(
+            "config.triggers.paused",
+            chat_id=chat_id_int,
+            crons=cron_count,
+            webhooks=webhook_count,
+        )
+    elif action == "resume" and mgr.resume():
+        logger.info(
+            "config.triggers.resumed",
+            chat_id=chat_id_int,
+            crons=cron_count,
+            webhooks=webhook_count,
+        )
+
+    is_paused = mgr.is_paused
+
+    lines = ["<b>⏰ Triggers</b>", ""]
+    if not has_any:
+        lines += [
+            "No crons or webhooks configured.",
+            "",
+            "Add <code>[[triggers.crons]]</code> or <code>[[triggers.webhooks]]</code> "
+            "entries to <code>untether.toml</code> — see the trigger docs.",
+        ]
+    else:
+        if is_paused:
+            lines += [
+                "Status: <b>⏸ paused</b>",
+                "",
+                "Crons and webhooks are temporarily suspended.",
+                f"<code>{cron_count}</code> cron · "
+                f"<code>{webhook_count}</code> webhook",
+                "",
+                "Pause is in-memory only — triggers auto-resume on restart.",
+            ]
+        else:
+            lines += [
+                "Status: <b>active</b>",
+                "",
+                f"<code>{cron_count}</code> cron · "
+                f"<code>{webhook_count}</code> webhook",
+            ]
+
+        # #271 Tier 2: per-chat trigger list. Only render when we can scope
+        # to the current chat — without chat_id we'd risk showing another
+        # group's triggers in a private chat.
+        if chat_id_int is not None:
+            default_tz = mgr.default_timezone
+            chat_crons = mgr.crons_for_chat(
+                chat_id_int, default_chat_id=ctx.default_chat_id
+            )
+            chat_webhooks = mgr.webhooks_for_chat(
+                chat_id_int, default_chat_id=ctx.default_chat_id
+            )
+
+            if chat_crons:
+                lines += ["", "<b>Crons</b>"]
+                for cron in chat_crons[:_TRIGGER_LIST_CAP]:
+                    schedule_text = describe_cron(
+                        cron.schedule, cron.timezone or default_tz
+                    )
+                    last = _format_trigger_relative(get_last_fired(cron.id))
+                    lines.append(
+                        f"<code>{cron.id}</code> · {schedule_text} · "
+                        f"proj=<i>{_truncate_field(cron.project)}</i> · "
+                        f"eng=<i>{_truncate_field(cron.engine)}</i> · "
+                        f"last <i>{last}</i>"
+                    )
+                overflow = len(chat_crons) - _TRIGGER_LIST_CAP
+                if overflow > 0:
+                    lines.append(
+                        f"…and {overflow} more (see <code>untether.toml</code>)"
+                    )
+
+            if chat_webhooks:
+                lines += ["", "<b>Webhooks</b>"]
+                for wh in chat_webhooks[:_TRIGGER_LIST_CAP]:
+                    last = _format_trigger_relative(get_last_fired(wh.id))
+                    lines.append(
+                        f"<code>{wh.id}</code> · <code>{wh.path}</code> · "
+                        f"auth=<i>{wh.auth}</i> · "
+                        f"proj=<i>{_truncate_field(wh.project)}</i> · "
+                        f"eng=<i>{_truncate_field(wh.engine)}</i> · "
+                        f"last <i>{last}</i>"
+                    )
+                overflow = len(chat_webhooks) - _TRIGGER_LIST_CAP
+                if overflow > 0:
+                    lines.append(
+                        f"…and {overflow} more (see <code>untether.toml</code>)"
+                    )
+
+    buttons: list[list[dict[str, str]]] = []
+    if has_any:
+        if is_paused:
+            buttons.append(
+                [
+                    {
+                        "text": "▶️ Resume triggers",
+                        "callback_data": "config:tg:resume",
+                    }
+                ]
+            )
+        else:
+            buttons.append(
+                [
+                    {
+                        "text": "⏸ Pause triggers",
+                        "callback_data": "config:tg:pause",
+                    }
+                ]
+            )
+    buttons.append([{"text": "← Back", "callback_data": "config:home"}])
+
+    await _respond(ctx, "\n".join(lines), buttons)
+
+
 # ---------------------------------------------------------------------------
 # Routing
 # ---------------------------------------------------------------------------
@@ -1819,6 +2168,7 @@ async def _page_about(ctx: CommandContext, action: str | None = None) -> None:
     "vb": _page_verbose,
     "ag": _page_engine,
     "tr": _page_trigger,
+    "tg": _page_triggers,
     "md": _page_model,
     "rs": _page_reasoning,
     "aq": _page_ask_questions,
@@ -1826,6 +2176,7 @@ async def _page_about(ctx: CommandContext, action: str | None = None) -> None:
     "cu": _page_cost_usage,
     "rl": _page_resume_line,
     "ab": _page_about,
+    "loop": _page_loop,
 }
 
 
@@ -1865,9 +2216,13 @@ def early_answer_toast(args_text: str) -> str | None:
             },
             "ag": {"clr": "Engine: cleared", "md_clr": "Model: cleared"},
             "tr": {
-                "all": "Trigger: all",
-                "men": "Trigger: mentions",
-                "clr": "Trigger: cleared",
+                "all": "Listen: all",
+                "men": "Listen: mentions",
+                "clr": "Listen: cleared",
+            },
+            "tg": {
+                "pause": "⏸ Triggers paused",
+                "resume": "▶️ Triggers resumed",
             },
             "md": {"clr": "Model: cleared"},
             "rs": {
@@ -1908,6 +2263,11 @@ def early_answer_toast(args_text: str) -> str | None:
                 "off": "Resume line: off",
                 "clr": "Resume line: cleared",
             },
+            "loop": {
+                "on": "🔁 Loop mode: on",
+                "off": "🔁 Loop mode: off",
+                "clr": "🔁 Loop mode: cleared",
+            },
         }
         page_labels = _TOAST_LABELS.get(page, {})
         if action in page_labels:
diff --git a/src/untether/telegram/commands/file_transfer.py b/src/untether/telegram/commands/file_transfer.py
index af335736..9dea48e0 100644
--- a/src/untether/telegram/commands/file_transfer.py
+++ b/src/untether/telegram/commands/file_transfer.py
@@ -5,6 +5,8 @@
 from pathlib import Path
 from typing import TYPE_CHECKING
 
+import anyio
+
 from ...config import ConfigError
 from ...context import RunContext
 from ...directives import DirectiveError
@@ -587,15 +589,24 @@ async def _handle_file_get(
             return
         filename = f"{rel_path.name or 'archive'}.zip"
     else:
+        # #211: read up to (max + 1) bytes in a single open() — no TOCTOU
+        # window between size check and read. If the file grew past the cap
+        # mid-read we'd still detect it via len(payload) here. The blocking
+        # read is offloaded to a worker thread to keep the event loop free.
+        max_bytes = cfg.files.max_download_bytes
+
+        def _read_capped() -> bytes:
+            with open(target, "rb") as f:
+                return f.read(max_bytes + 1)
+
         try:
-            size = target.stat().st_size
-            if size > cfg.files.max_download_bytes:
-                await reply(text="file is too large to send.")
-                return
-            payload = target.read_bytes()
+            payload = await anyio.to_thread.run_sync(_read_capped)
         except OSError as exc:
             await reply(text=f"failed to read file: {exc}")
             return
+        if len(payload) > max_bytes:
+            await reply(text="file is too large to send.")
+            return
         filename = target.name
     if len(payload) > cfg.files.max_download_bytes:
         await reply(text="file is too large to send.")
diff --git a/src/untether/telegram/commands/handlers.py b/src/untether/telegram/commands/handlers.py
index 77155fa1..e64be78d 100644
--- a/src/untether/telegram/commands/handlers.py
+++ b/src/untether/telegram/commands/handlers.py
@@ -9,6 +9,7 @@
 from .file_transfer import _handle_file_command as handle_file_command
 from .file_transfer import _handle_file_put_default as handle_file_put_default
 from .file_transfer import _save_file_put as save_file_put
+from .listen import _handle_listen_command as handle_listen_command
 from .media import _handle_media_group as handle_media_group
 from .menu import _reserved_commands as get_reserved_commands
 from .menu import _set_command_menu as set_command_menu
@@ -20,7 +21,10 @@
 from .topics import _handle_ctx_command as handle_ctx_command
 from .topics import _handle_new_command as handle_new_command
 from .topics import _handle_topic_command as handle_topic_command
-from .trigger import _handle_trigger_command as handle_trigger_command
+
+# #297: legacy alias preserved for one release cycle. Routes /trigger to the
+# listen handler with a deprecation prefix.
+handle_trigger_command = handle_listen_command
 
 __all__ = [
     "dispatch_callback",
@@ -32,6 +36,7 @@
     "handle_ctx_command",
     "handle_file_command",
     "handle_file_put_default",
+    "handle_listen_command",
     "handle_media_group",
     "handle_model_command",
     "handle_new_command",
diff --git a/src/untether/telegram/commands/trigger.py b/src/untether/telegram/commands/listen.py
similarity index 55%
rename from src/untether/telegram/commands/trigger.py
rename to src/untether/telegram/commands/listen.py
index ab93441e..09321989 100644
--- a/src/untether/telegram/commands/trigger.py
+++ b/src/untether/telegram/commands/listen.py
@@ -5,9 +5,9 @@
 from ...logging import get_logger
 from ..chat_prefs import ChatPrefsStore
 from ..files import split_command_args
+from ..listen_mode import resolve_listen_mode
 from ..topic_state import TopicStateStore
 from ..topics import _topic_key
-from ..trigger_mode import resolve_trigger_mode
 from ..types import TelegramIncomingMessage
 from .overrides import check_admin_or_private
 from .plan import ActionPlan
@@ -18,12 +18,16 @@
 
 logger = get_logger(__name__)
 
-TRIGGER_USAGE = (
-    "usage: `/trigger`, `/trigger all`, `/trigger mentions`, or `/trigger clear`"
+LISTEN_USAGE = "usage: `/listen`, `/listen all`, `/listen mentions`, or `/listen clear`"
+
+# #297: kept for one release as a deprecated alias. /trigger routes here.
+DEPRECATED_TRIGGER_NOTICE = (
+    "⚠️ `/trigger` is now `/listen`. The old name still works but will be "
+    "removed in a future release.\n\n"
 )
 
 
-async def _handle_trigger_command(
+async def _handle_listen_command(
     cfg: TelegramBridgeConfig,
     msg: TelegramIncomingMessage,
     args_text: str,
@@ -33,9 +37,10 @@ async def _handle_trigger_command(
     *,
     resolved_scope: str | None = None,
     scope_chat_ids: frozenset[int] | None = None,
+    invoked_as: str = "listen",
 ) -> None:
     reply = make_reply(cfg, msg)
-    plan = await _plan_trigger_command(
+    plan = await _plan_listen_command(
         cfg,
         msg,
         args_text=args_text,
@@ -43,10 +48,15 @@ async def _handle_trigger_command(
         chat_prefs=chat_prefs,
         scope_chat_ids=scope_chat_ids,
     )
+    if invoked_as == "trigger" and plan.reply_text:
+        plan = ActionPlan(
+            reply_text=DEPRECATED_TRIGGER_NOTICE + plan.reply_text,
+            actions=plan.actions,
+        )
     await plan.execute(reply)
 
 
-async def _plan_trigger_command(
+async def _plan_listen_command(
     cfg: TelegramBridgeConfig,
     msg: TelegramIncomingMessage,
     *,
@@ -60,7 +70,7 @@ async def _plan_trigger_command(
     action = tokens[0].lower() if tokens else "show"
 
     if action in {"show", ""}:
-        resolved = await resolve_trigger_mode(
+        resolved = await resolve_listen_mode(
             chat_id=msg.chat_id,
             thread_id=msg.thread_id,
             chat_prefs=chat_prefs,
@@ -68,17 +78,17 @@ async def _plan_trigger_command(
         )
         topic_mode = None
         if tkey is not None and topic_store is not None:
-            topic_mode = await topic_store.get_trigger_mode(tkey[0], tkey[1])
+            topic_mode = await topic_store.get_listen_mode(tkey[0], tkey[1])
         chat_mode = None
         if chat_prefs is not None:
-            chat_mode = await chat_prefs.get_trigger_mode(msg.chat_id)
+            chat_mode = await chat_prefs.get_listen_mode(msg.chat_id)
         if topic_mode is not None:
             source = "topic override"
         elif chat_mode is not None:
             source = "chat default"
         else:
             source = "default"
-        trigger_line = f"trigger: **{resolved}** ({source})"
+        listen_line = f"listen: **{resolved}** ({source})"
         topic_label = topic_mode or "none"
         if tkey is None:
             topic_label = "none"
@@ -86,63 +96,63 @@ async def _plan_trigger_command(
         defaults_line = f"defaults: topic: {topic_label}, chat: {chat_label}"
         available_line = "available: all, mentions"
         return ActionPlan(
-            reply_text="\n\n".join([trigger_line, defaults_line, available_line])
+            reply_text="\n\n".join([listen_line, defaults_line, available_line])
         )
 
     if action in {"all", "mentions"}:
-        logger.info("trigger.set", chat_id=msg.chat_id, mode=action)
+        logger.info("listen.set", chat_id=msg.chat_id, mode=action)
         decision = await check_admin_or_private(
             cfg,
             msg,
-            missing_sender="cannot verify sender for trigger settings.",
-            failed_member="failed to verify trigger permissions.",
-            denied="changing trigger mode is restricted to group admins.",
+            missing_sender="cannot verify sender for listen settings.",
+            failed_member="failed to verify listen permissions.",
+            denied="changing listen mode is restricted to group admins.",
         )
         if not decision.allowed:
-            return ActionPlan(reply_text=decision.error_text or TRIGGER_USAGE)
+            return ActionPlan(reply_text=decision.error_text or LISTEN_USAGE)
         if tkey is not None:
             if topic_store is None:
-                return ActionPlan(reply_text="topic trigger settings are unavailable.")
+                return ActionPlan(reply_text="topic listen settings are unavailable.")
             return ActionPlan(
-                reply_text=f"topic trigger mode **set to** `{action}`",
+                reply_text=f"topic listen mode **set to** `{action}`",
                 actions=(
-                    lambda: topic_store.set_trigger_mode(tkey[0], tkey[1], action),
+                    lambda: topic_store.set_listen_mode(tkey[0], tkey[1], action),
                 ),
             )
         if chat_prefs is None:
             return ActionPlan(
-                reply_text="chat trigger settings are unavailable (no config path)."
+                reply_text="chat listen settings are unavailable (no config path)."
             )
         return ActionPlan(
-            reply_text=f"chat trigger mode **set to** `{action}`",
-            actions=(lambda: chat_prefs.set_trigger_mode(msg.chat_id, action),),
+            reply_text=f"chat listen mode **set to** `{action}`",
+            actions=(lambda: chat_prefs.set_listen_mode(msg.chat_id, action),),
         )
 
     if action == "clear":
-        logger.info("trigger.clear", chat_id=msg.chat_id)
+        logger.info("listen.clear", chat_id=msg.chat_id)
         decision = await check_admin_or_private(
             cfg,
             msg,
-            missing_sender="cannot verify sender for trigger settings.",
-            failed_member="failed to verify trigger permissions.",
-            denied="changing trigger mode is restricted to group admins.",
+            missing_sender="cannot verify sender for listen settings.",
+            failed_member="failed to verify listen permissions.",
+            denied="changing listen mode is restricted to group admins.",
         )
         if not decision.allowed:
-            return ActionPlan(reply_text=decision.error_text or TRIGGER_USAGE)
+            return ActionPlan(reply_text=decision.error_text or LISTEN_USAGE)
         if tkey is not None:
             if topic_store is None:
-                return ActionPlan(reply_text="topic trigger settings are unavailable.")
+                return ActionPlan(reply_text="topic listen settings are unavailable.")
             return ActionPlan(
-                reply_text="topic trigger mode **cleared** (using chat default).",
-                actions=(lambda: topic_store.clear_trigger_mode(tkey[0], tkey[1]),),
+                reply_text="topic listen mode **cleared** (using chat default).",
+                actions=(lambda: topic_store.clear_listen_mode(tkey[0], tkey[1]),),
             )
         if chat_prefs is None:
             return ActionPlan(
-                reply_text="chat trigger settings are unavailable (no config path)."
+                reply_text="chat listen settings are unavailable (no config path)."
             )
         return ActionPlan(
-            reply_text="chat trigger mode **reset** to `all`.",
-            actions=(lambda: chat_prefs.clear_trigger_mode(msg.chat_id),),
+            reply_text="chat listen mode **reset** to `all`.",
+            actions=(lambda: chat_prefs.clear_listen_mode(msg.chat_id),),
         )
 
-    return ActionPlan(reply_text=TRIGGER_USAGE)
+    return ActionPlan(reply_text=LISTEN_USAGE)
diff --git a/src/untether/telegram/commands/menu.py b/src/untether/telegram/commands/menu.py
index f932b08f..74a38377 100644
--- a/src/untether/telegram/commands/menu.py
+++ b/src/untether/telegram/commands/menu.py
@@ -77,7 +77,9 @@ def build_bot_commands(
         ("agent", "set default engine"),
         ("model", "set model override"),
         ("reasoning", "set reasoning override"),
-        ("trigger", "set trigger mode"),
+        # #297: renamed from "trigger" → "listen". /trigger still works as
+        # a deprecated alias but does not appear in the command menu.
+        ("listen", "set listen mode (all/mentions)"),
     ]:
         if cmd in seen:
             continue
diff --git a/src/untether/telegram/commands/ping.py b/src/untether/telegram/commands/ping.py
index 44d9cc66..759a70f9 100644
--- a/src/untether/telegram/commands/ping.py
+++ b/src/untether/telegram/commands/ping.py
@@ -42,6 +42,7 @@ def _trigger_indicator(ctx: CommandContext) -> str | None:
     Returns ``None`` if the chat has no triggers targeting it. Formats:
     - Single cron: ``\u23f0 triggers: 1 cron (daily-review, 9:00 AM daily (Melbourne))``
     - Multiple: ``\u23f0 triggers: 2 crons, 1 webhook``
+    - Paused (#294): prefix with ``\u23f8`` and append ``(paused)``
     """
     mgr = ctx.trigger_manager
     if mgr is None:
@@ -67,7 +68,10 @@ def _trigger_indicator(ctx: CommandContext) -> str | None:
     if webhooks:
         suffix = "s" if len(webhooks) != 1 else ""
         parts.append(f"{len(webhooks)} webhook{suffix}")
-    return "\u23f0 triggers: " + ", ".join(parts)
+    line = "\u23f0 triggers: " + ", ".join(parts)
+    if mgr.is_paused:
+        line = "\u23f8 triggers paused: " + ", ".join(parts) + " (suspended)"
+    return line
 
 
 class PingCommand:
diff --git a/src/untether/telegram/commands/stats.py b/src/untether/telegram/commands/stats.py
index 4498d584..971ed42c 100644
--- a/src/untether/telegram/commands/stats.py
+++ b/src/untether/telegram/commands/stats.py
@@ -61,23 +61,33 @@ def format_stats_message(
     total_runs = 0
     total_actions = 0
     total_duration = 0
+    total_triggered = 0
+    total_manual = 0
 
     for s in sorted(stats, key=lambda x: x.run_count, reverse=True):
+        breakdown = ""
+        if s.triggered_count or s.manual_count:
+            breakdown = f" ({s.triggered_count} triggered, {s.manual_count} manual)"
         lines.append(
             f"<b>{s.engine}</b>: {s.run_count} runs, "
             f"{s.action_count} actions, "
             f"{_format_duration(s.duration_ms)}, "
-            f"last {_format_last_run(s.last_run_ts)}"
+            f"last {_format_last_run(s.last_run_ts)}{breakdown}"
         )
         total_runs += s.run_count
         total_actions += s.action_count
         total_duration += s.duration_ms
+        total_triggered += s.triggered_count
+        total_manual += s.manual_count
 
     if len(stats) > 1:
+        total_breakdown = ""
+        if total_triggered or total_manual:
+            total_breakdown = f" ({total_triggered} triggered, {total_manual} manual)"
         lines.append(
             f"\n<b>Total</b>: {total_runs} runs, "
             f"{total_actions} actions, "
-            f"{_format_duration(total_duration)}"
+            f"{_format_duration(total_duration)}{total_breakdown}"
         )
 
     return "\n".join(lines)
diff --git a/src/untether/telegram/commands/topics.py b/src/untether/telegram/commands/topics.py
index 40e930a3..40d7e150 100644
--- a/src/untether/telegram/commands/topics.py
+++ b/src/untether/telegram/commands/topics.py
@@ -43,7 +43,9 @@ def _cancel_chat_tasks(
 ) -> int:
     """Cancel all running tasks for a chat.
 
-    Returns the number of tasks cancelled.
+    Returns the number of tasks cancelled.  Also drops any pending /loop
+    entries for the chat (#289) so ``/new`` cleanly resets loop state in
+    addition to running runs.
     """
     cancelled = 0
     if running_tasks:
@@ -51,6 +53,11 @@ def _cancel_chat_tasks(
             if ref.channel_id == chat_id and not task.cancel_requested.is_set():
                 task.cancel_requested.set()
                 cancelled += 1
+    # #289: drop pending loop entries for the chat too.  Mirror the at
+    # scheduler integration in handle_cancel — /new should leave no trace.
+    from ... import loop_scheduler
+
+    cancelled += loop_scheduler.cancel_pending_for_chat(chat_id)
     return cancelled
 
 
diff --git a/src/untether/telegram/commands/usage.py b/src/untether/telegram/commands/usage.py
index 8c01dd08..17670659 100644
--- a/src/untether/telegram/commands/usage.py
+++ b/src/untether/telegram/commands/usage.py
@@ -62,22 +62,47 @@ def _time_until(iso_ts: str) -> str:
         return "unknown"
 
 
-def _read_access_token(
+def _read_token_expiry_ms(
     credentials_path: Path = _DEFAULT_CREDENTIALS_PATH,
-) -> tuple[str, bool]:
-    """Read the OAuth access token from Claude Code credentials.
-
-    Tries the plain-text file first (Linux), then macOS Keychain.
-    Returns (token, is_expired) tuple.
-    Raises FileNotFoundError if no credentials found.
+) -> int | None:
+    """Return the OAuth token's ``expiresAt`` (ms since epoch), or ``None``.
+
+    #410: surfaced in the ``/usage debug`` section so operators can see
+    whether a silent footer is the result of token expiry vs upstream API
+    error vs schema drift, without grepping ``journalctl``. Best-effort —
+    swallows every credential-read exception and returns ``None`` so the
+    debug section degrades gracefully.
     """
-    raw: str | None = None
+    try:
+        _, _, expires_at_ms = _read_access_token_with_expiry(credentials_path)
+    except Exception:  # noqa: BLE001
+        return None
+    return expires_at_ms
+
 
-    # Try plain-text file first (Linux, or custom CLAUDE_CONFIG_DIR)
+def _read_access_token_with_expiry(
+    credentials_path: Path = _DEFAULT_CREDENTIALS_PATH,
+) -> tuple[str, bool, int]:
+    """Like ``_read_access_token`` but also returns ``expires_at_ms`` (#410)."""
+    raw = _read_credentials_raw(credentials_path)
+    if raw is None:
+        raise FileNotFoundError(
+            f"No Claude Code credentials at {credentials_path} or macOS Keychain"
+        )
+    data = json.loads(raw)
+    oauth = data["claudeAiOauth"]
+    token = oauth["accessToken"]
+    expires_at_ms = oauth.get("expiresAt", 0)
+    is_expired = (time.time() * 1000) >= (expires_at_ms - 300_000)
+    return token, is_expired, expires_at_ms
+
+
+def _read_credentials_raw(credentials_path: Path) -> str | None:
+    """Shared credential-blob reader for ``_read_access_token`` and the
+    expiry helper (#410). Returns the raw JSON text or ``None``."""
+    raw: str | None = None
     with contextlib.suppress(FileNotFoundError):
         raw = credentials_path.read_text()
-
-    # macOS: try Keychain
     if raw is None and sys.platform == "darwin":
         try:
             # #202: `security` is the system Keychain CLI (/usr/bin/security).
@@ -99,17 +124,22 @@ def _read_access_token(
                 raw = result.stdout.strip()
         except (subprocess.TimeoutExpired, FileNotFoundError, OSError):
             pass
+    return raw
 
-    if raw is None:
-        raise FileNotFoundError(
-            f"No Claude Code credentials at {credentials_path} or macOS Keychain"
-        )
 
-    data = json.loads(raw)
-    oauth = data["claudeAiOauth"]
-    token = oauth["accessToken"]
-    expires_at_ms = oauth.get("expiresAt", 0)
-    is_expired = (time.time() * 1000) >= (expires_at_ms - 300_000)  # 5min buffer
+def _read_access_token(
+    credentials_path: Path = _DEFAULT_CREDENTIALS_PATH,
+) -> tuple[str, bool]:
+    """Read the OAuth access token from Claude Code credentials.
+
+    Tries the plain-text file first (Linux), then macOS Keychain.
+    Returns (token, is_expired) tuple.
+    Raises FileNotFoundError if no credentials found.
+
+    #410: now a thin shim around ``_read_access_token_with_expiry`` so the
+    debug surface and the runtime fetch path stay in sync.
+    """
+    token, is_expired, _ = _read_access_token_with_expiry(credentials_path)
     return token, is_expired
 
 
@@ -206,6 +236,67 @@ def format_usage(data: dict) -> str:
     return "\n".join(lines)
 
 
+def _format_debug_section() -> str:
+    """Render the ``/usage debug`` block (#410).
+
+    Surfaces: last successful fetch wall time, cache age, last error, OAuth
+    token expiry, schema-mismatch counter. Operator-facing signal so a
+    silent subscription footer can be triaged without grepping
+    ``journalctl``.
+    """
+    from ...runner_bridge import get_usage_schema_mismatch_count
+    from ...utils.usage_cache import get_cache_stats
+
+    stats = get_cache_stats()
+    mismatch = get_usage_schema_mismatch_count()
+    expiry_ms = _read_token_expiry_ms()
+
+    lines: list[str] = ["", "<b>🔧 debug</b>"]
+
+    if stats.last_success_wall_seconds is None:
+        lines.append("• cache: no successful fetch yet")
+    else:
+        wall = datetime.fromtimestamp(
+            stats.last_success_wall_seconds, tz=UTC
+        ).isoformat(timespec="seconds")
+        age = stats.cache_age_seconds
+        age_label = "fresh" if age is not None and age <= 60 else "stale"
+        if age is not None:
+            lines.append(f"• cache: last success {wall} ({age:.0f}s ago, {age_label})")
+        else:
+            lines.append(f"• cache: last success {wall}")
+
+    if stats.last_error_kind:
+        msg = stats.last_error_message or "(no message)"
+        # Truncate long messages so the debug block stays compact.
+        if len(msg) > 120:
+            msg = msg[:117] + "…"
+        lines.append(f"• last error: <code>{stats.last_error_kind}</code>: {msg}")
+    else:
+        lines.append("• last error: none")
+
+    if expiry_ms:
+        expiry_dt = datetime.fromtimestamp(expiry_ms / 1000, tz=UTC).isoformat(
+            timespec="seconds"
+        )
+        remaining_ms = expiry_ms - int(time.time() * 1000)
+        if remaining_ms <= 0:
+            lines.append(f"• OAuth token: expired ({expiry_dt})")
+        else:
+            mins = remaining_ms // 60_000
+            if mins >= 60:
+                hours = mins // 60
+                rem = mins % 60
+                lines.append(f"• OAuth token: expires {expiry_dt} (in {hours}h {rem}m)")
+            else:
+                lines.append(f"• OAuth token: expires {expiry_dt} (in {mins}m)")
+    else:
+        lines.append("• OAuth token: expiry unknown")
+
+    lines.append(f"• schema mismatches this process: {mismatch}")
+    return "\n".join(lines)
+
+
 class UsageCommand:
     """Command backend for Claude Code usage reporting."""
 
@@ -216,6 +307,10 @@ async def handle(self, ctx: CommandContext) -> CommandResult | None:
         from ..engine_overrides import SUBSCRIPTION_USAGE_SUPPORTED_ENGINES
         from ._resolve_engine import resolve_effective_engine
 
+        # #410: ``/usage debug`` appends a debug section with cache age,
+        # last error, OAuth token expiry, and the schema-mismatch counter.
+        debug_mode = ctx.args_text.strip().lower() == "debug"
+
         current_engine = await resolve_effective_engine(ctx)
         if current_engine not in SUBSCRIPTION_USAGE_SUPPORTED_ENGINES:
             return CommandResult(
@@ -279,6 +374,12 @@ async def handle(self, ctx: CommandContext) -> CommandResult | None:
             )
 
         text = format_usage(data)
+        if debug_mode:
+            # #410: HTML-formatted debug section uses <b>/<code> tags so the
+            # structured fields render legibly on mobile. Switch parse_mode
+            # accordingly so Telegram renders them.
+            text = text + "\n" + _format_debug_section()
+            return CommandResult(text=text, notify=True, parse_mode="HTML")
         return CommandResult(text=text, notify=True)
 
 
diff --git a/src/untether/telegram/engine_overrides.py b/src/untether/telegram/engine_overrides.py
index 67d513fe..266ddeec 100644
--- a/src/untether/telegram/engine_overrides.py
+++ b/src/untether/telegram/engine_overrides.py
@@ -26,6 +26,10 @@
 
 API_COST_SUPPORTED_ENGINES = frozenset({"claude", "opencode", "gemini", "amp"})
 
+# /loop and ScheduleWakeup observation (#289) is Claude-only — other engines
+# don't have session-scoped scheduling tools.
+LOOP_SUPPORTED_ENGINES = frozenset({"claude"})
+
 
 class EngineOverrides(msgspec.Struct, forbid_unknown_fields=False):
     model: str | None = None
@@ -38,6 +42,7 @@ class EngineOverrides(msgspec.Struct, forbid_unknown_fields=False):
     show_resume_line: bool | None = None
     budget_enabled: bool | None = None
     budget_auto_cancel: bool | None = None
+    loop_enabled: bool | None = None
 
 
 @dataclass(frozen=True, slots=True)
@@ -68,6 +73,7 @@ def normalize_overrides(overrides: EngineOverrides | None) -> EngineOverrides |
     show_resume_line = overrides.show_resume_line
     budget_enabled = overrides.budget_enabled
     budget_auto_cancel = overrides.budget_auto_cancel
+    loop_enabled = overrides.loop_enabled
     if (
         model is None
         and reasoning is None
@@ -79,6 +85,7 @@ def normalize_overrides(overrides: EngineOverrides | None) -> EngineOverrides |
         and show_resume_line is None
         and budget_enabled is None
         and budget_auto_cancel is None
+        and loop_enabled is None
     ):
         return None
     return EngineOverrides(
@@ -92,6 +99,7 @@ def normalize_overrides(overrides: EngineOverrides | None) -> EngineOverrides |
         show_resume_line=show_resume_line,
         budget_enabled=budget_enabled,
         budget_auto_cancel=budget_auto_cancel,
+        loop_enabled=loop_enabled,
     )
 
 
@@ -153,6 +161,11 @@ def merge_overrides(
         budget_auto_cancel = topic.budget_auto_cancel
     elif chat is not None:
         budget_auto_cancel = chat.budget_auto_cancel
+    loop_enabled = None
+    if topic is not None and topic.loop_enabled is not None:
+        loop_enabled = topic.loop_enabled
+    elif chat is not None:
+        loop_enabled = chat.loop_enabled
     return normalize_overrides(
         EngineOverrides(
             model=model,
@@ -165,6 +178,7 @@ def merge_overrides(
             show_resume_line=show_resume_line,
             budget_enabled=budget_enabled,
             budget_auto_cancel=budget_auto_cancel,
+            loop_enabled=loop_enabled,
         )
     )
 
diff --git a/src/untether/telegram/trigger_mode.py b/src/untether/telegram/listen_mode.py
similarity index 81%
rename from src/untether/telegram/trigger_mode.py
rename to src/untether/telegram/listen_mode.py
index 6f70ab84..dfe7ccbc 100644
--- a/src/untether/telegram/trigger_mode.py
+++ b/src/untether/telegram/listen_mode.py
@@ -8,22 +8,25 @@
 from .topic_state import TopicStateStore
 from .types import TelegramIncomingMessage
 
-TriggerMode = Literal["all", "mentions"]
+# Renamed from "TriggerMode" → "ListenMode" in #297 to disambiguate from
+# webhook/cron triggers. The msgspec storage field is still named
+# `trigger_mode` for backward compat with existing state files.
+ListenMode = Literal["all", "mentions"]
 
 
-async def resolve_trigger_mode(
+async def resolve_listen_mode(
     *,
     chat_id: int,
     thread_id: int | None,
     chat_prefs: ChatPrefsStore | None,
     topic_store: TopicStateStore | None,
-) -> TriggerMode:
+) -> ListenMode:
     if topic_store is not None and thread_id is not None:
-        topic_mode = await topic_store.get_trigger_mode(chat_id, thread_id)
+        topic_mode = await topic_store.get_listen_mode(chat_id, thread_id)
         if topic_mode == "mentions":
             return "mentions"
     if chat_prefs is not None:
-        chat_mode = await chat_prefs.get_trigger_mode(chat_id)
+        chat_mode = await chat_prefs.get_listen_mode(chat_id)
         if chat_mode == "mentions":
             return "mentions"
     return "all"
diff --git a/src/untether/telegram/loop.py b/src/untether/telegram/loop.py
index 029cbebc..6f380233 100644
--- a/src/untether/telegram/loop.py
+++ b/src/untether/telegram/loop.py
@@ -41,12 +41,12 @@
     handle_ctx_command,
     handle_file_command,
     handle_file_put_default,
+    handle_listen_command,
     handle_media_group,
     handle_model_command,
     handle_new_command,
     handle_reasoning_command,
     handle_topic_command,
-    handle_trigger_command,
     parse_callback_data,
     parse_slash_command,
     run_engine,
@@ -59,6 +59,7 @@
 from .context import _merge_topic_context, _usage_ctx_set, _usage_topic
 from .engine_defaults import resolve_engine_for_message
 from .engine_overrides import merge_overrides
+from .listen_mode import resolve_listen_mode, should_trigger_run
 from .topic_state import TopicStateStore, resolve_state_path
 from .topics import (
     _maybe_rename_topic,
@@ -68,7 +69,6 @@
     _topics_chat_project,
     _validate_topics_setup,
 )
-from .trigger_mode import resolve_trigger_mode, should_trigger_run
 from .types import (
     TelegramCallbackQuery,
     TelegramIncomingMessage,
@@ -129,6 +129,7 @@ async def _resolve_engine_run_options(
         show_resume_line=merged.show_resume_line,
         budget_enabled=merged.budget_enabled,
         budget_auto_cancel=merged.budget_auto_cancel,
+        loop_enabled=merged.loop_enabled,
     )
 
 
@@ -400,9 +401,11 @@ async def _stateless_new() -> None:
         task_group.start_soon(handler)
         return True
 
-    if command_id == "trigger":
+    if command_id in {"listen", "trigger"}:
+        # #297: /trigger is a deprecated alias for /listen. The handler
+        # prepends a deprecation notice when invoked_as="trigger".
         handler = partial(
-            handle_trigger_command,
+            handle_listen_command,
             cfg,
             msg,
             args_text,
@@ -411,6 +414,7 @@ async def _stateless_new() -> None:
             chat_prefs,
             resolved_scope=resolved_scope,
             scope_chat_ids=scope_chat_ids,
+            invoked_as=command_id,
         )
         task_group.start_soon(handler)
         return True
@@ -1003,14 +1007,14 @@ async def _flush_media_group(self, key: tuple[int, str]) -> None:
             del self._groups[key]
             if not messages:
                 return
-            trigger_mode = await resolve_trigger_mode(
+            listen_mode = await resolve_listen_mode(
                 chat_id=messages[0].chat_id,
                 thread_id=messages[0].thread_id,
                 chat_prefs=self._chat_prefs,
                 topic_store=self._topic_store,
             )
             command_ids = self._command_ids()
-            if trigger_mode == "mentions" and not any(
+            if listen_mode == "mentions" and not any(
                 should_trigger_run(
                     msg,
                     bot_username=self._bot_username,
@@ -1305,8 +1309,10 @@ def refresh_commands() -> None:
                 state_path=str(resolve_prefs_path(config_path)),
             )
             from ..session_stats import init_stats
+            from ..triggers.history import init_history
 
             init_stats(config_path)
+            init_history(config_path)
         if cfg.session_mode == "chat":
             if config_path is None:
                 raise ConfigError(
@@ -1346,7 +1352,7 @@ def refresh_commands() -> None:
             me = await cfg.bot.get_me()
         except Exception as exc:  # noqa: BLE001
             logger.info(
-                "trigger_mode.bot_username.failed",
+                "listen_mode.bot_username.failed",
                 error=str(exc),
                 error_type=exc.__class__.__name__,
             )
@@ -1354,7 +1360,7 @@ def refresh_commands() -> None:
         if me is not None and me.username:
             state.bot_username = me.username.lower()
         else:
-            logger.info("trigger_mode.bot_username.unavailable")
+            logger.info("listen_mode.bot_username.unavailable")
         # Install graceful shutdown signal handlers
 
         def _shutdown_handler(signum: int, frame: object) -> None:
@@ -1495,10 +1501,18 @@ async def _drain_and_exit() -> None:
 
                 active = len(state.running_tasks)
                 pending_at = at_scheduler.active_count()
+                # #289: include loop fires in the shutdown summary so ops
+                # can see how many were pending at drain time.  Pending
+                # loops are persisted to disk; the task-group cancel below
+                # cancels their in-flight `_arm_timer` sleeps cleanly.
+                from .. import loop_scheduler
+
+                pending_loops = loop_scheduler.active_count()
                 logger.info(
                     "shutdown.draining",
                     active_runs=active,
                     pending_at=pending_at,
+                    pending_loops=pending_loops,
                 )
 
                 if active > 0:
@@ -1688,6 +1702,33 @@ async def run_thread_job(job: ThreadJob) -> None:
                 cfg.chat_id,
             )
 
+            # --- /loop and ScheduleWakeup observation (#289) ---
+            from .. import loop_scheduler
+
+            loop_state_path = None
+            config_path_for_loops = cfg.runtime.config_path
+            if config_path_for_loops is not None:
+                loop_state_path = config_path_for_loops.with_name(
+                    loop_scheduler.STATE_FILENAME
+                )
+
+            def _is_chat_busy(chat_id_in: int) -> bool:
+                """Drop a loop fire if the chat already has a run in flight
+                — mirrors upstream's "no catch-up" semantic."""
+                for ref in state.running_tasks:
+                    if getattr(ref, "channel_id", None) == chat_id_in:
+                        return True
+                return False
+
+            loop_scheduler.install(
+                tg,
+                run_job,
+                cfg.exec_cfg.transport,
+                cfg.chat_id,
+                state_path=loop_state_path,
+                is_chat_busy=_is_chat_busy,
+            )
+
             # --- Trigger system (webhooks + cron) ---
             trigger_manager: TriggerManager | None = None
             if cfg.trigger_config and cfg.trigger_config.get("enabled"):
@@ -2181,13 +2222,13 @@ async def route_message(msg: TelegramIncomingMessage) -> None:
                 ):
                     return
 
-                trigger_mode = await resolve_trigger_mode(
+                listen_mode = await resolve_listen_mode(
                     chat_id=chat_id,
                     thread_id=msg.thread_id,
                     chat_prefs=state.chat_prefs,
                     topic_store=state.topic_store,
                 )
-                if trigger_mode == "mentions" and not should_trigger_run(
+                if listen_mode == "mentions" and not should_trigger_run(
                     msg,
                     bot_username=state.bot_username,
                     runtime=cfg.runtime,
@@ -2205,7 +2246,11 @@ async def route_message(msg: TelegramIncomingMessage) -> None:
                         max_bytes=cfg.voice_max_bytes,
                         reply=reply,
                         base_url=cfg.voice_transcription_base_url,
-                        api_key=cfg.voice_transcription_api_key,
+                        api_key=(
+                            cfg.voice_transcription_api_key.get_secret_value()
+                            if cfg.voice_transcription_api_key is not None
+                            else None
+                        ),
                     )
                     if text is None:
                         return
@@ -2295,11 +2340,10 @@ async def route_message(msg: TelegramIncomingMessage) -> None:
                     from ..runners.claude import (
                         answer_ask_question,
                         answer_ask_question_with_options,
-                        format_question_message,
                         get_ask_question_flow,
                         get_pending_ask_request,
-                        get_question_option_buttons,
                     )
+                    from .commands.ask_question import send_next_ask_question_message
 
                     # Check for active option flow in "Other" text mode first
                     flow = get_ask_question_flow(channel_id=msg.chat_id)
@@ -2314,21 +2358,16 @@ async def route_message(msg: TelegramIncomingMessage) -> None:
                         flow.current_index += 1
 
                         if flow.current_index < len(flow.questions):
-                            # More questions — show next one
-                            # Note: we can't easily edit the progress message from
-                            # here, so just send a new message with the next question
-                            msg_text = format_question_message(flow)
-                            buttons = get_question_option_buttons(flow)
-                            from ..transport import RenderedMessage as _RM
-
-                            next_msg = _RM(
-                                text=msg_text,
-                                extra={
-                                    "parse_mode": "HTML",
-                                    "reply_markup": {"inline_keyboard": buttons},
-                                },
+                            # More questions — send next one as a new message
+                            # (callback-button continuation edits in place via
+                            # ctx.executor.edit; see commands/ask_question.py).
+                            await send_next_ask_question_message(
+                                cfg.exec_cfg.transport,
+                                chat_id=chat_id,
+                                user_msg_id=msg.message_id,
+                                thread_id=msg.thread_id,
+                                flow=flow,
                             )
-                            await reply(text=next_msg)
                             return
                         else:
                             # All done — send structured answer
@@ -2379,13 +2418,17 @@ async def route_message(msg: TelegramIncomingMessage) -> None:
                     return
                 forward_coalescer.schedule(pending)
 
-            # rc4 (#286): read allowed_user_ids from cfg on each update so
-            # hot-reload of the allowlist takes effect immediately.
-            if not cfg.allowed_user_ids:
-                logger.warning(
-                    "security.no_allowed_users",
-                    hint="allowed_user_ids is empty — any user in the chat can run commands. "
-                    "Set [transports.telegram] allowed_user_ids to restrict access.",
+            # #377: empty `allowed_user_ids` is now a startup ConfigError
+            # (see TelegramTransportSettings._validate_allowed_user_ids_or_optin).
+            # The only way to reach this hook with no allowlist is the explicit
+            # `allow_any_user = true` opt-in — log it at INFO every boot so the
+            # deviation stays visible in journalctl.
+            if getattr(cfg, "allow_any_user", False) or not cfg.allowed_user_ids:
+                logger.info(
+                    "security.allow_any_user",
+                    hint="allow_any_user=true is in effect — bot accepts "
+                    "commands from any Telegram user. Intended for "
+                    "demos/dev only.",
                 )
 
             async def _safe_answer_callback(query_id: str) -> None:
diff --git a/src/untether/telegram/onboarding.py b/src/untether/telegram/onboarding.py
index 18eb3493..8358567c 100644
--- a/src/untether/telegram/onboarding.py
+++ b/src/untether/telegram/onboarding.py
@@ -364,7 +364,7 @@ def render_botfather_instructions() -> Text:
     return Text.assemble(
         "  1. open telegram and message @BotFather\n",
         "  2. send /newbot and follow the prompts\n",
-        "  3. copy the token (looks like 123456789:ABCdef...)",
+        "  3. copy the token (looks like <BOT_ID>:<BOT_TOKEN>)",
     )
 
 
@@ -814,7 +814,7 @@ async def step_token_and_bot(ui: UI, svc: Services, state: OnboardingState) -> N
     if not have_token:
         ui.print(render_botfather_instructions(), markup=False)
     else:
-        ui.print("  token looks like 123456789:ABCdef...")
+        ui.print("  token looks like <BOT_ID>:<BOT_TOKEN>")
     token, info = await prompt_token(ui, svc)
     state.token = token
     state.bot_username = info.username
diff --git a/src/untether/telegram/topic_state.py b/src/untether/telegram/topic_state.py
index e07f5127..6f5d5ff0 100644
--- a/src/untether/telegram/topic_state.py
+++ b/src/untether/telegram/topic_state.py
@@ -65,7 +65,7 @@ def _normalize_text(value: str | None) -> str | None:
     return value or None
 
 
-def _normalize_trigger_mode(value: str | None) -> str | None:
+def _normalize_listen_mode(value: str | None) -> str | None:
     if value is None:
         return None
     value = value.strip().lower()
@@ -76,6 +76,10 @@ def _normalize_trigger_mode(value: str | None) -> str | None:
     return None
 
 
+# #297: legacy alias kept so external imports don't break in this release.
+_normalize_trigger_mode = _normalize_listen_mode
+
+
 def _normalize_engine_id(value: str | None) -> str | None:
     if value is None:
         return None
@@ -188,13 +192,17 @@ async def get_default_engine(self, chat_id: int, thread_id: int) -> str | None:
                 return None
             return _normalize_text(thread.default_engine)
 
-    async def get_trigger_mode(self, chat_id: int, thread_id: int) -> str | None:
+    async def get_listen_mode(self, chat_id: int, thread_id: int) -> str | None:
         async with self._lock:
             self._reload_locked_if_needed()
             thread = self._get_thread_locked(chat_id, thread_id)
             if thread is None:
                 return None
-            return _normalize_trigger_mode(thread.trigger_mode)
+            return _normalize_listen_mode(thread.trigger_mode)
+
+    # #297: legacy alias preserved for one release cycle.
+    async def get_trigger_mode(self, chat_id: int, thread_id: int) -> str | None:
+        return await self.get_listen_mode(chat_id, thread_id)
 
     async def get_engine_override(
         self, chat_id: int, thread_id: int, engine: str
@@ -223,18 +231,27 @@ async def set_default_engine(
     async def clear_default_engine(self, chat_id: int, thread_id: int) -> None:
         await self.set_default_engine(chat_id, thread_id, None)
 
-    async def set_trigger_mode(
+    async def set_listen_mode(
         self, chat_id: int, thread_id: int, mode: str | None
     ) -> None:
-        normalized = _normalize_trigger_mode(mode)
+        normalized = _normalize_listen_mode(mode)
         async with self._lock:
             self._reload_locked_if_needed()
             thread = self._ensure_thread_locked(chat_id, thread_id)
             thread.trigger_mode = normalized
             self._save_locked()
 
+    async def clear_listen_mode(self, chat_id: int, thread_id: int) -> None:
+        await self.set_listen_mode(chat_id, thread_id, None)
+
+    # #297: legacy aliases preserved for one release cycle.
+    async def set_trigger_mode(
+        self, chat_id: int, thread_id: int, mode: str | None
+    ) -> None:
+        await self.set_listen_mode(chat_id, thread_id, mode)
+
     async def clear_trigger_mode(self, chat_id: int, thread_id: int) -> None:
-        await self.set_trigger_mode(chat_id, thread_id, None)
+        await self.clear_listen_mode(chat_id, thread_id)
 
     async def set_engine_override(
         self,
diff --git a/src/untether/triggers/cron.py b/src/untether/triggers/cron.py
index 43504128..5e3bc75e 100644
--- a/src/untether/triggers/cron.py
+++ b/src/untether/triggers/cron.py
@@ -98,6 +98,12 @@ async def run_cron_scheduler(
 
     while True:
         utc_now = datetime.datetime.now(datetime.UTC)
+        # #294: master pause flag — skip every cron's tick when set.
+        # `run_once` crons that would have fired during the pause are NOT
+        # consumed; they fire on the next matching tick after resume.
+        if manager.is_paused:
+            await anyio.sleep(60 - utc_now.second + 0.1)
+            continue
         # Snapshot the cron list for this tick — safe even if update()
         # replaces manager._crons mid-iteration (new list, old ref valid).
         crons = manager.crons
@@ -122,6 +128,14 @@ async def run_cron_scheduler(
                 last_fired[cron.id] = key
                 logger.info("triggers.cron.firing", cron_id=cron.id)
                 await dispatcher.dispatch_cron(cron)
+                # #271 Tier 3: record last-fired-at after dispatch returns.
+                # `dispatch_cron` only blocks until the notification is
+                # queued, not run completion — recording here means the
+                # `/config:tg` page reflects every dispatched cron, even if
+                # the run later fails.
+                from . import history
+
+                history.record_fired(cron.id)
                 # #288: one-shot crons are removed from the active list
                 # after firing; they stay in the TOML and re-activate on
                 # the next config reload or restart.
diff --git a/src/untether/triggers/dispatcher.py b/src/untether/triggers/dispatcher.py
index 5686d439..2cdc6950 100644
--- a/src/untether/triggers/dispatcher.py
+++ b/src/untether/triggers/dispatcher.py
@@ -40,6 +40,12 @@ async def dispatch_webhook(self, webhook: WebhookConfig, prompt: str) -> None:
         label = f"\N{HIGH VOLTAGE SIGN} Trigger: webhook:{webhook.id}"
 
         await self._dispatch(chat_id, label, prompt, context, engine_override)
+        # #271 Tier 3: record last-fired-at for the /config:tg page. Recorded
+        # after dispatch so a transport-send failure (logged inside _dispatch)
+        # doesn't pollute the history with a phantom entry.
+        from . import history
+
+        history.record_fired(webhook.id)
 
     async def dispatch_cron(self, cron: CronConfig) -> None:
         chat_id = cron.chat_id or self.default_chat_id
@@ -208,3 +214,8 @@ async def dispatch_action(
             ok=ok,
             message=msg,
         )
+        # #271 Tier 3: record last-fired-at for non-agent actions too — the
+        # webhook still fired even if it didn't spawn a run.
+        from . import history
+
+        history.record_fired(webhook.id)
diff --git a/src/untether/triggers/history.py b/src/untether/triggers/history.py
new file mode 100644
index 00000000..0cf89dbc
--- /dev/null
+++ b/src/untether/triggers/history.py
@@ -0,0 +1,119 @@
+"""Persistent ``last_fired_at`` history for cron + webhook triggers (#271 Tier 3).
+
+Single-writer JSON file at ``<config_path>.with_name("triggers_history.json")``.
+Mirrors the ``session_stats`` pattern: simple JSON, ``atomic_write_json``, a
+module-level singleton initialised once at startup. Recording is best-effort —
+a write failure is logged and swallowed so a corrupted state file can't break
+the cron loop or webhook server.
+"""
+
+from __future__ import annotations
+
+import json
+import time
+from dataclasses import dataclass, field
+from pathlib import Path
+
+from ..logging import get_logger
+from ..utils.json_state import atomic_write_json
+
+logger = get_logger(__name__)
+
+STATE_FILENAME = "triggers_history.json"
+_STATE_VERSION = 1
+
+
+@dataclass
+class TriggerHistoryStore:
+    """JSON-backed last-fired-at timestamps keyed by trigger id."""
+
+    path: Path
+    _data: dict = field(default_factory=dict, repr=False)
+
+    def __post_init__(self) -> None:
+        self._load()
+
+    def _load(self) -> None:
+        if not self.path.exists():
+            self._data = {"version": _STATE_VERSION, "triggers": {}}
+            return
+        try:
+            raw = json.loads(self.path.read_text(encoding="utf-8"))
+        except (json.JSONDecodeError, OSError) as exc:
+            logger.warning(
+                "triggers.history.load_failed",
+                path=str(self.path),
+                error=str(exc),
+            )
+            self._data = {"version": _STATE_VERSION, "triggers": {}}
+            return
+        if not isinstance(raw, dict) or raw.get("version") != _STATE_VERSION:
+            logger.warning("triggers.history.version_mismatch", path=str(self.path))
+            self._data = {"version": _STATE_VERSION, "triggers": {}}
+            return
+        triggers = raw.get("triggers")
+        if not isinstance(triggers, dict):
+            triggers = {}
+        self._data = {"version": _STATE_VERSION, "triggers": triggers}
+
+    def _save(self) -> None:
+        atomic_write_json(self.path, self._data)
+
+    def record_fired(self, trigger_id: str) -> None:
+        triggers = self._data.setdefault("triggers", {})
+        triggers[trigger_id] = time.time()
+        self._save()
+
+    def get_last_fired(self, trigger_id: str) -> float | None:
+        triggers = self._data.get("triggers", {})
+        value = triggers.get(trigger_id)
+        if isinstance(value, int | float):
+            return float(value)
+        return None
+
+
+# ── Module-level convenience ───────────────────────────────────────────────
+
+_store: TriggerHistoryStore | None = None
+
+
+def init_history(config_path: Path) -> None:
+    """Initialise the module-level history store. Idempotent."""
+    global _store
+    history_path = config_path.with_name(STATE_FILENAME)
+    _store = TriggerHistoryStore(history_path)
+
+
+def reset_history() -> None:
+    """Reset the module singleton. Intended for tests."""
+    global _store
+    _store = None
+
+
+def record_fired(trigger_id: str) -> None:
+    """Record a trigger firing. No-op if the store isn't initialised.
+
+    Wraps the underlying write in a best-effort try/except so a transient
+    disk failure can't break the cron loop or webhook dispatch path.
+    """
+    if _store is None:
+        return
+    try:
+        _store.record_fired(trigger_id)
+    except OSError as exc:
+        logger.warning(
+            "triggers.history.write_failed",
+            trigger_id=trigger_id,
+            error=str(exc),
+        )
+
+
+def get_last_fired(trigger_id: str) -> float | None:
+    """Return the unix timestamp of the trigger's last firing, or None."""
+    if _store is None:
+        return None
+    return _store.get_last_fired(trigger_id)
+
+
+def resolve_history_path(config_path: Path) -> Path:
+    return config_path.with_name(STATE_FILENAME)
diff --git a/src/untether/triggers/manager.py b/src/untether/triggers/manager.py
index e15682fd..1b9071dc 100644
--- a/src/untether/triggers/manager.py
+++ b/src/untether/triggers/manager.py
@@ -37,6 +37,7 @@ class TriggerManager:
         "_crons",
         "_default_timezone",
         "_fired_run_once",
+        "_paused",
         "_run_once_state_path",
         "_webhooks_by_path",
     )
@@ -50,6 +51,11 @@ def __init__(
         self._crons: list[CronConfig] = []
         self._webhooks_by_path: dict[str, WebhookConfig] = {}
         self._default_timezone: str | None = None
+        # #294: master pause flag — in-memory only (no persistence). Triggers
+        # auto-resume on restart, which is the safe default. Set via
+        # pause()/resume(); read by the cron scheduler each tick and by the
+        # webhook server on each request.
+        self._paused: bool = False
         # #317: persistent fired-state for ``run_once`` crons so restarts
         # and config hot-reloads don't re-fire already-completed one-shots.
         # ``config_path=None`` keeps the old in-memory-only behaviour (used
@@ -203,3 +209,36 @@ def _persist_fired_state(self) -> None:
     def fired_run_once_ids(self) -> list[str]:
         """Return a snapshot of cron ids that have already fired (#317)."""
         return sorted(self._fired_run_once)
+
+    # ------------------------------------------------------------------ #
+    # #294: master pause toggle
+    # ------------------------------------------------------------------ #
+
+    @property
+    def is_paused(self) -> bool:
+        """Whether the master trigger pause flag is set."""
+        return self._paused
+
+    def pause(self) -> bool:
+        """Pause all trigger dispatch. Returns ``True`` if state changed."""
+        if self._paused:
+            return False
+        self._paused = True
+        logger.info(
+            "triggers.manager.paused",
+            crons=len(self._crons),
+            webhooks=len(self._webhooks_by_path),
+        )
+        return True
+
+    def resume(self) -> bool:
+        """Resume trigger dispatch. Returns ``True`` if state changed."""
+        if not self._paused:
+            return False
+        self._paused = False
+        logger.info(
+            "triggers.manager.resumed",
+            crons=len(self._crons),
+            webhooks=len(self._webhooks_by_path),
+        )
+        return True
diff --git a/src/untether/triggers/server.py b/src/untether/triggers/server.py
index 2c7623d9..04d2c49b 100644
--- a/src/untether/triggers/server.py
+++ b/src/untether/triggers/server.py
@@ -217,8 +217,17 @@ def _webhook_count() -> int:
                 )
 
     async def handle_health(request: web.Request) -> web.Response:
+        # #294: surface paused state on the health endpoint so external
+        # monitors can tell paused-but-up apart from healthy-and-active.
+        paused = manager is not None and manager.is_paused
         return web.Response(
-            text=json.dumps({"status": "ok", "webhooks": _webhook_count()}),
+            text=json.dumps(
+                {
+                    "status": "paused" if paused else "ok",
+                    "webhooks": _webhook_count(),
+                    "paused": paused,
+                }
+            ),
             content_type="application/json",
         )
 
@@ -228,6 +237,20 @@ async def handle_webhook(request: web.Request) -> web.Response:
         if webhook is None:
             return web.Response(status=404, text="not found")
 
+        # #294: master pause — return 503 (not 404) so callers can
+        # distinguish "route exists but is paused" from "route does not exist".
+        if manager is not None and manager.is_paused:
+            logger.info(
+                "triggers.webhook.paused_skipped",
+                webhook_id=webhook.id,
+                path=path,
+            )
+            return web.Response(
+                status=503,
+                text="triggers paused",
+                headers={"Retry-After": "60"},
+            )
+
         try:
             return await _process_webhook(request, webhook, path)
         except Exception:
diff --git a/src/untether/utils/env_audit.py b/src/untether/utils/env_audit.py
index e74f0d23..b100c554 100644
--- a/src/untether/utils/env_audit.py
+++ b/src/untether/utils/env_audit.py
@@ -18,7 +18,7 @@
 import sys
 from collections.abc import Iterable
 
-from .env_policy import is_allowed
+from .env_policy import is_allowed_with_extras
 
 
 def read_proc_environ(pid: int) -> dict[str, str] | None:
@@ -47,6 +47,8 @@ def audit_proc_env(
     pid: int,
     *,
     expected_extras: Iterable[str] = (),
+    user_extra_exact: Iterable[str] = (),
+    user_extra_prefix: Iterable[str] = (),
 ) -> list[str]:
     """Return sorted names present in ``/proc/<pid>/environ`` that aren't
     in the env_policy allowlist.
@@ -57,13 +59,24 @@ def audit_proc_env(
     ``expected_extras`` lets the caller permit per-engine vars that
     aren't in the global allowlist (e.g. a runner sets a specific
     ``X_INTERNAL_TOKEN`` itself).
+
+    ``user_extra_exact`` / ``user_extra_prefix`` (#409) thread per-
+    deployment user extras through so audit doesn't false-flag names the
+    user opted into via ``[security] env_extra_allow``.
     """
     env = read_proc_environ(pid)
     if not env:
         return []
-    allowed_extras = frozenset(expected_extras)
+    runner_extras = frozenset(expected_extras)
     return sorted(
-        name for name in env if not is_allowed(name) and name not in allowed_extras
+        name
+        for name in env
+        if name not in runner_extras
+        and not is_allowed_with_extras(
+            name,
+            extra_exact=user_extra_exact,
+            extra_prefix=user_extra_prefix,
+        )
     )
 
 
diff --git a/src/untether/utils/env_policy.py b/src/untether/utils/env_policy.py
index 54740f54..4c1e2e1c 100644
--- a/src/untether/utils/env_policy.py
+++ b/src/untether/utils/env_policy.py
@@ -1,4 +1,4 @@
-"""Allowlist-based env filter for engine subprocesses (#198).
+"""Allowlist-based env filter for engine subprocesses (#198, #409).
 
 Background
 ----------
@@ -29,11 +29,24 @@
 Extending the allowlist
 -----------------------
 
-If a new engine or MCP needs a variable that isn't allowlisted, it
-hangs at init with no useful error. Add the variable below, ship a
-test in ``tests/test_env_policy.py``, and run the integration suite.
+There are two ways to extend the allowlist:
+
+1. **Built-in defaults** (this module). Add the variable to
+   ``_EXACT_ALLOW`` or ``_PREFIX_ALLOW``, ship a test in
+   ``tests/test_env_policy.py``, and run the integration suite. Use
+   this for vars that *every* user is likely to need.
+
+2. **Per-deployment config** (#409). Set
+   ``[security] env_extra_allow = [...]`` and
+   ``env_extra_prefix_allow = [...]`` in ``untether.toml``. The
+   runners pass these through to :func:`filtered_env` so the user
+   doesn't need to fork or vendor-patch this module to thread a
+   credential-manager token (``OP_SERVICE_ACCOUNT_TOKEN``,
+   ``DOPPLER_TOKEN``, ``VAULT_*``, etc.) to engine subprocesses.
+
 The set of NAMESPACE prefixes is deliberately narrow — add another
-prefix only when there's a clear family of vars (e.g. all ``XDG_*``).
+default prefix only when there's a clear family of vars (e.g. all
+``XDG_*``). User-defined extras are filtered to the same name shape.
 """
 
 from __future__ import annotations
@@ -41,6 +54,10 @@
 import os
 from collections.abc import Iterable, Mapping
 
+from ..logging import get_logger
+
+logger = get_logger(__name__)
+
 # Exact-match allowlist. One entry per variable.
 _EXACT_ALLOW: frozenset[str] = frozenset(
     {
@@ -118,6 +135,10 @@
         # Cloudflare — for MCP servers accessing CF APIs.
         "CLOUDFLARE_API_TOKEN",
         "CLOUDFLARE_ACCOUNT_ID",
+        # Bitwarden Secrets Manager — used by MCP bash wrappers that
+        # call `kc_get` / `bws secret` to materialise per-project
+        # credentials (Trello, Jina, Pal, etc.). See issue #409.
+        "BWS_ACCESS_TOKEN",
         # Untether-set markers — Claude hooks look for UNTETHER_SESSION.
         "UNTETHER_SESSION",
         # direnv-provided workspace context.
@@ -157,6 +178,26 @@ def is_allowed(name: str) -> bool:
     return any(name.startswith(prefix) for prefix in _PREFIX_ALLOW)
 
 
+def is_allowed_with_extras(
+    name: str,
+    *,
+    extra_exact: Iterable[str] = (),
+    extra_prefix: Iterable[str] = (),
+) -> bool:
+    """Like :func:`is_allowed` but also honours per-deployment user extras (#409).
+
+    ``extra_exact`` and ``extra_prefix`` come from
+    ``[security] env_extra_allow`` / ``env_extra_prefix_allow`` in
+    ``untether.toml``. The audit module passes them through so live-
+    process audits don't false-flag user-allowed names as leaks.
+    """
+    if is_allowed(name):
+        return True
+    if name in frozenset(extra_exact):
+        return True
+    return any(name.startswith(prefix) for prefix in extra_prefix)
+
+
 # Back-compat alias for any external importers that depended on the
 # previously-private name. Safe to remove once we've audited all consumers.
 _is_allowed = is_allowed
@@ -166,6 +207,7 @@ def filtered_env(
     source: Mapping[str, str] | None = None,
     *,
     extra_allow: Iterable[str] = (),
+    extra_prefix: Iterable[str] = (),
 ) -> dict[str, str]:
     """Return a filtered copy of `source` containing only allowlisted keys.
 
@@ -176,6 +218,10 @@ def filtered_env(
     extra_allow : Iterable[str]
         Additional exact variable names to allow for this call (e.g.
         per-engine / per-site keys that don't belong in the global set).
+    extra_prefix : Iterable[str]
+        Additional name prefixes to allow (#409 — surfaces
+        ``[security] env_extra_prefix_allow`` so users can pass through
+        credential-manager families like ``VAULT_*``).
 
     Returns
     -------
@@ -184,8 +230,61 @@ def filtered_env(
     """
     if source is None:
         source = os.environ
-    extras = frozenset(extra_allow)
-    return {k: v for k, v in source.items() if is_allowed(k) or k in extras}
+    extras_exact = frozenset(extra_allow)
+    extras_prefix = tuple(extra_prefix)
+    return {
+        k: v
+        for k, v in source.items()
+        if is_allowed_with_extras(
+            k, extra_exact=extras_exact, extra_prefix=extras_prefix
+        )
+    }
+
+
+# Module-level latch so we emit `env_policy.user_extension` at most once
+# per process even if multiple runners (Claude + Pi) call it. Reset is
+# only useful in tests; expose the underlying flag via _RESET_LOG_LATCH.
+_extension_logged = False
+
+
+def log_user_extensions_once(
+    extra_exact: Iterable[str] = (),
+    extra_prefix: Iterable[str] = (),
+) -> None:
+    """Emit a single INFO log naming user-supplied env-policy extras (#409).
+
+    Idempotent — re-invocations after the first non-empty call are
+    no-ops so journalctl shows one record per process per restart, not
+    one per spawned subprocess.
+    """
+    global _extension_logged
+    if _extension_logged:
+        return
+    exact = sorted(set(extra_exact))
+    prefix = sorted(set(extra_prefix))
+    if not exact and not prefix:
+        return
+    logger.info(
+        "env_policy.user_extension",
+        extra_exact=exact,
+        extra_prefix=prefix,
+        hint=(
+            "user-extended subprocess env allowlist via "
+            "[security] env_extra_allow / env_extra_prefix_allow"
+        ),
+    )
+    _extension_logged = True
+
+
+def _reset_log_latch_for_tests() -> None:
+    """Clear the once-per-process log latch. Tests only."""
+    global _extension_logged
+    _extension_logged = False
 
 
-__all__ = ["filtered_env", "is_allowed"]
+__all__ = [
+    "filtered_env",
+    "is_allowed",
+    "is_allowed_with_extras",
+    "log_user_extensions_once",
+]
diff --git a/src/untether/utils/usage_cache.py b/src/untether/utils/usage_cache.py
index 57417886..df1f2e35 100644
--- a/src/untether/utils/usage_cache.py
+++ b/src/untether/utils/usage_cache.py
@@ -6,11 +6,17 @@
 cache falls back to the last successful response if one is still held in
 memory (stale-while-error); otherwise the underlying exception propagates so
 callers can handle it like before.
+
+#410: also tracks observability state (last successful fetch wall-clock time,
+last error class+message, schema-mismatch count) for the ``/usage`` debug
+section so the next time the subscription footer goes silent the operator
+can see why without grepping ``journalctl``.
 """
 
 from __future__ import annotations
 
 import time
+from dataclasses import dataclass
 from typing import Any
 
 import anyio
@@ -25,6 +31,25 @@
 _lock: anyio.Lock | None = None
 
 
+@dataclass(frozen=True, slots=True)
+class UsageCacheStats:
+    """Snapshot of usage-cache observability state for ``/usage`` debug (#410)."""
+
+    last_success_wall_seconds: float | None
+    """``time.time()`` value of the last successful fetch, or None."""
+    cache_age_seconds: float | None
+    """Seconds since the last successful fetch (relative to wall clock), or None."""
+    last_error_kind: str | None
+    """Exception class name from the most recent fetch failure, or None."""
+    last_error_message: str | None
+    """Exception message from the most recent fetch failure, or None."""
+
+
+_last_success_wall: float | None = None
+_last_error_kind: str | None = None
+_last_error_message: str | None = None
+
+
 def _get_lock() -> anyio.Lock:
     global _lock
     if _lock is None:
@@ -34,9 +59,25 @@ def _get_lock() -> anyio.Lock:
 
 def reset_cache() -> None:
     """Clear the cache and lock. Intended for tests."""
-    global _cache, _lock
+    global _cache, _lock, _last_success_wall, _last_error_kind, _last_error_message
     _cache = None
     _lock = None
+    _last_success_wall = None
+    _last_error_kind = None
+    _last_error_message = None
+
+
+def get_cache_stats() -> UsageCacheStats:
+    """Return a snapshot of cache observability state (#410)."""
+    age: float | None = None
+    if _last_success_wall is not None:
+        age = max(0.0, time.time() - _last_success_wall)
+    return UsageCacheStats(
+        last_success_wall_seconds=_last_success_wall,
+        cache_age_seconds=age,
+        last_error_kind=_last_error_kind,
+        last_error_message=_last_error_message,
+    )
 
 
 async def fetch_claude_usage_cached() -> dict[str, Any]:
@@ -47,7 +88,7 @@ async def fetch_claude_usage_cached() -> dict[str, Any]:
     underlying fetch raises, returns the stale cached value if present;
     otherwise re-raises so the caller's existing error handling still fires.
     """
-    global _cache
+    global _cache, _last_success_wall, _last_error_kind, _last_error_message
     from ..telegram.commands.usage import fetch_claude_usage
 
     now = time.monotonic()
@@ -59,11 +100,16 @@ async def fetch_claude_usage_cached() -> dict[str, Any]:
 
         try:
             data = await fetch_claude_usage()
-        except Exception:
+        except Exception as exc:
+            _last_error_kind = type(exc).__name__
+            _last_error_message = str(exc) or repr(exc)
             if _cache is not None:
                 logger.debug("claude_usage.cache.stale_on_error")
                 return _cache[1]
             raise
 
+        _last_success_wall = time.time()
+        _last_error_kind = None
+        _last_error_message = None
         _cache = (now, data)
         return data
diff --git a/tests/test_amp_runner.py b/tests/test_amp_runner.py
index a8d28d54..dc814295 100644
--- a/tests/test_amp_runner.py
+++ b/tests/test_amp_runner.py
@@ -341,7 +341,8 @@ def test_translate_result_without_cost_still_returns_tokens() -> None:
 
 
 def test_build_args_new_session() -> None:
-    runner = AmpRunner()
+    # #206: default dangerously_allow_all is now False; explicit opt-in required.
+    runner = AmpRunner(dangerously_allow_all=True)
     state = AmpStreamState()
     args = runner.build_args("hello world", None, state=state)
     assert "--stream-json" in args
@@ -370,6 +371,21 @@ def test_build_args_dangerously_allow_all_false() -> None:
     assert "--dangerously-allow-all" not in args
 
 
+def test_build_args_default_is_safe() -> None:
+    # #206: default flipped to False; --dangerously-allow-all must be opt-in.
+    runner = AmpRunner()
+    state = AmpStreamState()
+    args = runner.build_args("hello", None, state=state)
+    assert "--dangerously-allow-all" not in args
+
+
+def test_build_args_dangerously_allow_all_true() -> None:
+    runner = AmpRunner(dangerously_allow_all=True)
+    state = AmpStreamState()
+    args = runner.build_args("hello", None, state=state)
+    assert "--dangerously-allow-all" in args
+
+
 def test_build_args_stream_json_input() -> None:
     runner = AmpRunner(stream_json_input=True)
     state = AmpStreamState()
diff --git a/tests/test_ask_user_question.py b/tests/test_ask_user_question.py
index 74512f2b..93c918d4 100644
--- a/tests/test_ask_user_question.py
+++ b/tests/test_ask_user_question.py
@@ -707,3 +707,107 @@ def test_translate_registers_ask_with_channel_id() -> None:
     channel_id, question = _PENDING_ASK_REQUESTS["req-chan-1"]
     assert channel_id == CHAT_A
     assert question == "Which?"
+
+
+# ---------------------------------------------------------------------------
+# Regression: #488 — multi-question flow text-reply continuation
+# ---------------------------------------------------------------------------
+
+
+class _RecordingTransport:
+    """Minimal Transport stub that records send/edit/delete calls."""
+
+    def __init__(self) -> None:
+        self.sent: list[tuple[int, object, object]] = []
+
+    async def send(self, *, channel_id, message, options=None):  # type: ignore[no-untyped-def]
+        self.sent.append((channel_id, message, options))
+        return
+
+    async def edit(self, ref, message, wait=True):  # type: ignore[no-untyped-def]
+        return None
+
+    async def delete(self, ref):  # type: ignore[no-untyped-def]
+        return None
+
+
+@pytest.mark.anyio
+async def test_send_next_ask_question_message_uses_rendered_message() -> None:
+    """Regression for #488: text-reply continuation must call transport.send
+    with a RenderedMessage carrying the inline keyboard, NOT pass it to
+    send_plain (which would TypeError on str-only `text` kwarg)."""
+    from untether.telegram.commands.ask_question import (
+        send_next_ask_question_message,
+    )
+    from untether.transport import MessageRef, RenderedMessage, SendOptions
+
+    flow = AskQuestionState(
+        request_id="req-488",
+        channel_id=-12345,
+        questions=[
+            {
+                "question": "First?",
+                "options": [{"label": "A"}, {"label": "B"}],
+            },
+            {
+                "question": "Second?",
+                "options": [{"label": "C"}, {"label": "D"}],
+            },
+        ],
+        current_index=1,  # user already answered Q1 by typing
+    )
+
+    transport = _RecordingTransport()
+
+    await send_next_ask_question_message(
+        transport,  # type: ignore[arg-type]
+        chat_id=-12345,
+        user_msg_id=678,
+        thread_id=42,
+        flow=flow,
+    )
+
+    assert len(transport.sent) == 1
+    channel_id, message, options = transport.sent[0]
+    assert channel_id == -12345
+    assert isinstance(message, RenderedMessage)
+    assert "2 of 2" in message.text
+    assert message.extra is not None
+    assert message.extra["parse_mode"] == "HTML"
+    assert "inline_keyboard" in message.extra["reply_markup"]
+    # Buttons present for question 2's options:
+    keyboard = message.extra["reply_markup"]["inline_keyboard"]
+    assert len(keyboard) >= 1
+    assert isinstance(options, SendOptions)
+    assert options.reply_to == MessageRef(channel_id=-12345, message_id=678)
+    assert options.thread_id == 42
+
+
+@pytest.mark.anyio
+async def test_send_next_ask_question_message_no_thread() -> None:
+    """thread_id=None passes through to SendOptions (private chats / non-forum groups)."""
+    from untether.telegram.commands.ask_question import (
+        send_next_ask_question_message,
+    )
+
+    flow = AskQuestionState(
+        request_id="req-488-b",
+        channel_id=-9999,
+        questions=[
+            {"question": "Q1", "options": [{"label": "A"}]},
+            {"question": "Q2", "options": [{"label": "B"}]},
+        ],
+        current_index=1,
+    )
+    transport = _RecordingTransport()
+
+    await send_next_ask_question_message(
+        transport,  # type: ignore[arg-type]
+        chat_id=-9999,
+        user_msg_id=1,
+        thread_id=None,
+        flow=flow,
+    )
+
+    _, _, options = transport.sent[0]
+    assert options.thread_id is None
diff --git a/tests/test_at_command.py b/tests/test_at_command.py
index ad242d01..a0ea0307 100644
--- a/tests/test_at_command.py
+++ b/tests/test_at_command.py
@@ -250,14 +250,44 @@ async def test_handle_captures_global_default_when_unmapped(self):
                 assert result is not None
                 pending = at_scheduler.pending_for_chat(99999)
                 assert len(pending) == 1
-                assert pending[0].context is None
-                # Resolved engine is captured even when context is None so a
+                # #271 follow-up: even unmapped chats now get a fresh
+                # RunContext carrying just the trigger_source so the footer
+                # renders `⏰ at:<token>`.
+                assert pending[0].context is not None
+                assert pending[0].context.project is None
+                assert pending[0].context.trigger_source is not None
+                assert pending[0].context.trigger_source.startswith("at:")
+                assert pending[0].context.trigger_source == f"at:{pending[0].token}"
+                # Resolved engine is captured even when project is None so a
                 # later config change to the global default can't drift the
                 # frozen run (mirrors cron.engine).
                 assert pending[0].engine_override == "codex"
             finally:
                 tg.cancel_scope.cancel()
 
+    async def test_handle_stamps_trigger_source_on_mapped_chat(self):
+        """#271 follow-up: /at preserves the project mapping AND stamps
+        trigger_source = 'at:<token>' so the run footer shows ⏰ at:<id>."""
+        runtime = _FakeRuntime(
+            chat_to_context={12345: RunContext(project="acme", branch=None)},
+            engine_for_context={"acme": "pi"},
+            global_default="codex",
+        )
+        run_recorder = RunJobRecorder()
+        transport = FakeTransport()
+        async with anyio.create_task_group() as tg:
+            at_scheduler.install(tg, run_recorder, transport, 12345)
+            try:
+                await AtCommand().handle(_make_ctx("60s do something", runtime=runtime))
+                pending = at_scheduler.pending_for_chat(12345)
+                assert len(pending) == 1
+                # Project mapping preserved (#362) AND trigger_source stamped.
+                assert pending[0].context is not None
+                assert pending[0].context.project == "acme"
+                assert pending[0].context.trigger_source == f"at:{pending[0].token}"
+            finally:
+                tg.cancel_scope.cancel()
+
 
 # ── Scheduler: schedule / cancel / drain ────────────────────────────────
 
@@ -358,7 +388,11 @@ async def test_run_delayed_forwards_captured_context_and_engine(self):
         #    progress_ref)
         assert args[0] == 555
         assert args[2] == "go"
-        assert args[4] == captured_context  # context (was None pre-#362)
+        # #362 captured project preserved; #271 follow-up stamps trigger_source.
+        assert args[4] is not None
+        assert args[4].project == captured_context.project
+        assert args[4].trigger_source is not None
+        assert args[4].trigger_source.startswith("at:")
         assert args[9] == "pi"  # engine_override (was None pre-#362)
 
 
diff --git a/tests/test_bridge_config_reload.py b/tests/test_bridge_config_reload.py
index e41fe362..efaa135f 100644
--- a/tests/test_bridge_config_reload.py
+++ b/tests/test_bridge_config_reload.py
@@ -20,6 +20,10 @@ def _settings(**overrides) -> TelegramTransportSettings:
     base = {
         "bot_token": "abc",
         "chat_id": 123,
+        # #377: tests don't care about user allowlisting; opt in to the
+        # explicit "open bot" so the model_validator doesn't reject these
+        # fixtures. Tests that do care set allowed_user_ids via overrides.
+        "allow_any_user": True,
     }
     base.update(overrides)
     return TelegramTransportSettings.model_validate(base)
@@ -76,7 +80,10 @@ def test_update_from_all_fields(self, cfg: TelegramBridgeConfig):
         assert cfg.voice_max_bytes == 1 * 1024 * 1024
         assert cfg.voice_transcription_model == "whisper-1"
         assert cfg.voice_transcription_base_url == "https://x/v1"
-        assert cfg.voice_transcription_api_key == "sk-new"
+        # #378: SecretStr — compare via .get_secret_value() since equality
+        # against a bare str returns False.
+        assert cfg.voice_transcription_api_key is not None
+        assert cfg.voice_transcription_api_key.get_secret_value() == "sk-new"
         assert cfg.voice_show_transcription is False
         assert cfg.show_resume_line is False
         assert cfg.forward_coalesce_s == 3.5
@@ -123,7 +130,9 @@ def test_update_from_preserves_identity_fields(self, cfg: TelegramBridgeConfig):
     def test_update_from_clears_voice_api_key(self, cfg: TelegramBridgeConfig):
         """Removing voice_transcription_api_key from config resets it to None."""
         cfg.update_from(_settings(voice_transcription_api_key="sk-before"))
-        assert cfg.voice_transcription_api_key == "sk-before"
+        # #378: SecretStr — equality is by SecretStr identity, not raw string.
+        assert cfg.voice_transcription_api_key is not None
+        assert cfg.voice_transcription_api_key.get_secret_value() == "sk-before"
         cfg.update_from(_settings())  # no voice_transcription_api_key
         assert cfg.voice_transcription_api_key is None
 
diff --git a/tests/test_build_args.py b/tests/test_build_args.py
index 8cd7b5bc..8a8c29d3 100644
--- a/tests/test_build_args.py
+++ b/tests/test_build_args.py
@@ -94,6 +94,136 @@ def test_allowed_tools(self) -> None:
         # Should be comma-separated list
         assert "Bash" in args[idx + 1]
 
+    def test_extra_args_default_empty(self) -> None:
+        """`extra_args=[]` produces byte-identical argv to the pre-#407
+        behaviour — no extra tokens introduced."""
+        runner_none = self._runner()
+        runner_empty = self._runner(extra_args=[])
+        from untether.runners.claude import ClaudeStreamState
+
+        state = ClaudeStreamState()
+        args_none = runner_none.build_args("hello", None, state=state)
+        args_empty = runner_empty.build_args("hello", None, state=state)
+        assert args_none == args_empty
+
+    def test_extra_args_chrome(self) -> None:
+        """`extra_args=['--chrome']` lands on argv after the managed
+        prelude and before resume/model/allowed-tools, and does not
+        displace the `-p <prompt>` suffix (#407)."""
+        runner = self._runner(extra_args=["--chrome"])
+        from untether.runners.claude import ClaudeStreamState
+
+        state = ClaudeStreamState()
+        token = ResumeToken(engine="claude", value="sess123")
+        args = runner.build_args("hello", token, state=state)
+        assert "--chrome" in args
+        chrome_idx = args.index("--chrome")
+        verbose_idx = args.index("--verbose")
+        resume_idx = args.index("--resume")
+        assert verbose_idx < chrome_idx < resume_idx
+        # Prompt still last after `--`
+        assert args[-2] == "--"
+        assert args[-1] == "hello"
+
+    def test_extra_args_chrome_permission_mode(self) -> None:
+        """`extra_args` survives the permission-mode argv path (no -p,
+        prompt sent via stdin)."""
+        runner = self._runner(extra_args=["--chrome"])
+        from untether.runners.claude import ClaudeStreamState
+
+        state = ClaudeStreamState()
+        opts = RunOptions(permission_mode="plan")
+        with patch("untether.runners.claude.get_run_options", return_value=opts):
+            args = runner.build_args("hello", None, state=state)
+        assert "--chrome" in args
+        assert "--permission-mode" in args
+        chrome_idx = args.index("--chrome")
+        perm_idx = args.index("--permission-mode")
+        assert chrome_idx < perm_idx
+        # permission-mode path sends prompt via stdin, no trailing `-- hello`
+        assert "--" not in args
+        assert "hello" not in args
+
+    def test_extra_args_multiple(self) -> None:
+        """Order between multiple user-supplied flags is preserved."""
+        runner = self._runner(extra_args=["--chrome", "--strict-mcp-config"])
+        from untether.runners.claude import ClaudeStreamState
+
+        state = ClaudeStreamState()
+        args = runner.build_args("hello", None, state=state)
+        chrome_idx = args.index("--chrome")
+        strict_idx = args.index("--strict-mcp-config")
+        assert chrome_idx < strict_idx
+
+
+class TestClaudeBuildRunner:
+    """Coverage for extra_args parsing + reserved-flag validation in
+    `build_runner` (#407)."""
+
+    def _call(self, config: dict[str, Any]):
+        from pathlib import Path
+
+        from untether.runners.claude import build_runner
+
+        return build_runner(config, Path("/tmp/untether.toml"))
+
+    def test_extra_args_missing_yields_empty(self) -> None:
+        runner = self._call({})
+        assert runner.extra_args == []
+
+    def test_extra_args_list_of_strings(self) -> None:
+        runner = self._call({"extra_args": ["--chrome"]})
+        assert runner.extra_args == ["--chrome"]
+
+    def test_extra_args_non_list_raises(self) -> None:
+        import pytest
+
+        from untether.config import ConfigError
+
+        with pytest.raises(ConfigError, match="list of strings"):
+            self._call({"extra_args": "--chrome"})
+
+    def test_extra_args_non_string_element_raises(self) -> None:
+        import pytest
+
+        from untether.config import ConfigError
+
+        with pytest.raises(ConfigError, match="list of strings"):
+            self._call({"extra_args": ["--chrome", 42]})
+
+    def test_reserved_flag_rejected(self) -> None:
+        import pytest
+
+        from untether.config import ConfigError
+
+        for reserved in (
+            "-p",
+            "--print",
+            "--output-format",
+            "--input-format",
+            "--resume",
+            "--continue",
+            "--permission-mode",
+            "--permission-prompt-tool",
+        ):
+            with pytest.raises(ConfigError, match="managed by Untether"):
+                self._call({"extra_args": [reserved]})
+
+    def test_reserved_prefix_rejected(self) -> None:
+        import pytest
+
+        from untether.config import ConfigError
+
+        with pytest.raises(ConfigError, match="managed by Untether"):
+            self._call({"extra_args": ["--output-format=text"]})
+
+    def test_non_reserved_flag_accepted(self) -> None:
+        # Sanity: `--chrome`, `--no-chrome`, `--mcp-config`, and other
+        # upstream flags Untether doesn't manage must pass through.
+        for flag in ("--chrome", "--no-chrome", "--mcp-config"):
+            runner = self._call({"extra_args": [flag]})
+            assert flag in runner.extra_args
+
 
 # ---------------------------------------------------------------------------
 # Codex
@@ -338,6 +468,24 @@ def test_run_options_none_defaults_to_yolo(self) -> None:
         idx = args.index("--approval-mode")
         assert args[idx + 1] == "yolo"
 
+    def test_skip_trust_default_includes_flag(self) -> None:
+        """#471 — runs should pass --skip-trust by default so headless runs
+        work outside ~/.gemini/trustedFolders.json."""
+        runner = self._runner()
+        state = runner.new_state("hello", None)
+        with patch("untether.runners.gemini.get_run_options", return_value=None):
+            args = runner.build_args("hello", None, state=state)
+        assert "--skip-trust" in args
+
+    def test_skip_trust_opt_out_omits_flag(self) -> None:
+        """#471 — `[gemini] skip_trust = false` opts out so Gemini's own
+        project-local trust gate is enforced (security-conscious deployments)."""
+        runner = self._runner(skip_trust=False)
+        state = runner.new_state("hello", None)
+        with patch("untether.runners.gemini.get_run_options", return_value=None):
+            args = runner.build_args("hello", None, state=state)
+        assert "--skip-trust" not in args
+
 
 # ---------------------------------------------------------------------------
 # AMP
@@ -398,9 +546,16 @@ def test_mode_from_config(self) -> None:
         assert args[idx + 1] == "rush"
 
     def test_dangerously_allow_all_default(self) -> None:
+        # #206: default is now safe — opt-in only via [amp] config.
         runner = self._runner()
         state = runner.new_state("hello", None)
         args = runner.build_args("hello", None, state=state)
+        assert "--dangerously-allow-all" not in args
+
+    def test_dangerously_allow_all_enabled(self) -> None:
+        runner = self._runner(dangerously_allow_all=True)
+        state = runner.new_state("hello", None)
+        args = runner.build_args("hello", None, state=state)
         assert "--dangerously-allow-all" in args
 
     def test_dangerously_allow_all_disabled(self) -> None:
diff --git a/tests/test_claude_control.py b/tests/test_claude_control.py
index 64353553..b645a853 100644
--- a/tests/test_claude_control.py
+++ b/tests/test_claude_control.py
@@ -2162,3 +2162,136 @@ async def test_normal_approve_edits_feedback_when_outline_ref_exists() -> None:
     assert "approved" in edit_text.lower()
     # Ref should be cleaned up
     assert session_id not in _DISCUSS_FEEDBACK_REFS
+
+
+# ---------------------------------------------------------------------------
+# #380 — Auto-approve safety invariant regression locks
+# ---------------------------------------------------------------------------
+
+
+class TestAutoApproveSafetyInvariant:
+    """Lock in the safety reasoning behind auto-approving the four non-tool
+    control_request subtypes. See the comment in
+    ``runners/claude.py::translate_claude_event`` near ``_AUTO_APPROVE_TYPES``
+    for the full audit. These tests fail loudly if the auto-approve path
+    starts inspecting payloads (which would signal that the trust model has
+    shifted and the audit needs to be revisited).
+    """
+
+    def test_mcp_message_payload_not_inspected(self) -> None:
+        """ControlMcpMessageRequest auto-approval does NOT inspect or mutate
+        the ``message`` payload — Untether is a transport pass-through.
+
+        A future change that started reading ``message`` here would mean we
+        need to add gates on its content; this test asserts we don't today.
+        """
+        state, _ = _make_state_with_session()
+        # Stick a tracer object in the payload — if any code stringifies or
+        # iterates it, our ``_TaintedPayload`` would record the call.
+        calls: list[str] = []
+
+        class _TaintedPayload:
+            def __iter__(self):
+                calls.append("iter")
+                return iter([])
+
+            def __repr__(self):
+                calls.append("repr")
+                return "<tainted>"
+
+            def __str__(self):
+                calls.append("str")
+                return "<tainted>"
+
+        request = {
+            "subtype": "mcp_message",
+            "server_name": "evil-mcp",
+            # msgspec decodes ``Any`` to a plain dict, so we can't pass a
+            # custom object through decode. Instead we use a sentinel string
+            # and assert the auto-approve path does not log it at INFO.
+            "message": {"prompt_injection": "ignore previous instructions"},
+        }
+        event = _decode_event(
+            {
+                "type": "control_request",
+                "request_id": "req-mcp-tainted",
+                "request": request,
+            }
+        )
+        events = translate_claude_event(
+            event, title="claude", state=state, factory=state.factory
+        )
+        # No events emitted (no Telegram-visible output).
+        assert events == []
+        # Request queued for auto-approval drain.
+        assert "req-mcp-tainted" in state.auto_approve_queue
+        # The request_id WAS registered in the input map (so updated_input
+        # round-trips). That's expected — the field is opaque storage.
+        assert "req-mcp-tainted" in _REQUEST_TO_INPUT
+        # The tracer wasn't touched — confirms no payload inspection happens.
+        assert calls == []
+
+    def test_rewind_files_request_does_not_clear_plan_approval(self) -> None:
+        """ControlRewindFilesRequest must not mutate the cross-session
+        approval state that prior decisions depended on.
+
+        The audit relies on rewind being user-initiated upstream, but as a
+        defence-in-depth check we also assert that handling a rewind request
+        does NOT touch ``_PLAN_EXIT_APPROVED`` or ``_DISCUSS_APPROVED``. A
+        future change that touched these registries from the rewind path
+        would break the safety invariant.
+        """
+        state, _ = _make_state_with_session("sess-rewind-1")
+        # Pre-populate the approval state to mimic an active session that
+        # already cleared ExitPlanMode.
+        _PLAN_EXIT_APPROVED.add("sess-rewind-1")
+        _DISCUSS_APPROVED.add("sess-rewind-1")
+        before_plan = set(_PLAN_EXIT_APPROVED)
+        before_discuss = set(_DISCUSS_APPROVED)
+
+        event = _decode_event(
+            {
+                "type": "control_request",
+                "request_id": "req-rewind-1",
+                "request": {
+                    "subtype": "rewind_files",
+                    "user_message_id": "msg-1",
+                },
+            }
+        )
+        events = translate_claude_event(
+            event, title="claude", state=state, factory=state.factory
+        )
+        assert events == []
+        assert "req-rewind-1" in state.auto_approve_queue
+        # Approval state untouched.
+        assert before_plan == _PLAN_EXIT_APPROVED
+        assert before_discuss == _DISCUSS_APPROVED
+
+    def test_auto_approve_emits_no_telegram_events(self) -> None:
+        """All five auto-approve subtypes return ``[]`` — no progress action,
+        no approval keyboard, nothing for the user to see. This is the
+        invariant that justifies skipping the Telegram-side gate."""
+        state, _ = _make_state_with_session()
+        for subtype, extra in [
+            ("initialize", {"hooks": None}),
+            ("hook_callback", {"callback_id": "cb-1", "input": {}}),
+            ("mcp_message", {"server_name": "srv", "message": {}}),
+            ("rewind_files", {"user_message_id": "msg-x"}),
+            ("interrupt", {}),
+        ]:
+            event = _decode_event(
+                {
+                    "type": "control_request",
+                    "request_id": f"req-{subtype}-events",
+                    "request": {"subtype": subtype, **extra},
+                }
+            )
+            events = translate_claude_event(
+                event, title="claude", state=state, factory=state.factory
+            )
+            assert events == [], (
+                f"auto-approve subtype {subtype!r} unexpectedly emitted events; "
+                "the safety invariant in runners/claude.py requires silent "
+                "auto-approve — re-audit if this fails."
+            )
diff --git a/tests/test_claude_runner.py b/tests/test_claude_runner.py
index d04c59eb..c7b80f2c 100644
--- a/tests/test_claude_runner.py
+++ b/tests/test_claude_runner.py
@@ -1,4 +1,6 @@
+import contextlib
 import json
+import time
 from pathlib import Path
 from typing import cast
 
@@ -172,6 +174,125 @@ class _Fake:
     assert runner._check_prespawn_ram_guard(resume=None) is None
 
 
+# ---------------------------------------------------------------------------
+# #478 / #205 — claude runner.start log must NOT carry prompt content at INFO
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.anyio
+async def test_runner_start_does_not_log_prompt_at_info(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """#478: ClaudeRunner.run_impl emits ``runner.start`` at INFO with only
+    ``prompt_len`` + ``args`` (no ``prompt`` field). The prompt preview
+    moves to a DEBUG ``runner.start_prompt`` companion event so credentials
+    or PII never surface at the broadly-accessible INFO tier (#205).
+    Regression-locks the duplicate INFO call inside the claude override
+    that was missed when the base runner was fixed.
+    """
+    from structlog.testing import capture_logs
+
+    class _BoomManager:
+        async def __aenter__(self) -> object:
+            raise RuntimeError("stop_after_log")
+
+        async def __aexit__(self, exc_type, exc, tb) -> None:
+            return None
+
+    def fake_manage_subprocess(*args: object, **kwargs: object) -> _BoomManager:
+        _ = args, kwargs
+        return _BoomManager()
+
+    monkeypatch.setattr(claude_runner, "manage_subprocess", fake_manage_subprocess)
+
+    # Force control-channel mode (production default). Without a
+    # permission_mode, build_args falls back to legacy ``-p <prompt>``
+    # which puts the prompt into argv — covered separately below.
+    runner = ClaudeRunner(claude_cmd="claude", permission_mode="acceptEdits")
+    # Distinctive sentinel that won't collide with legitimate env var names
+    # (e.g., GEMINI_API_KEY) which appear redacted in args=[...].
+    sentinel = "ZAPHOD-PROMPT-SECRET-XYZZY-9876"
+    secret_prompt = f"sensitive content: {sentinel} run my task"
+
+    with capture_logs() as logs, contextlib.suppress(RuntimeError):
+        async for _evt in runner.run_impl(secret_prompt, None):
+            pass
+
+    start_events = [r for r in logs if r.get("event") == "runner.start"]
+    assert start_events, "runner.start INFO event must fire"
+    for record in start_events:
+        # Prompt content must NOT appear in the INFO log under any field name.
+        assert "prompt" not in record, (
+            f"runner.start at INFO leaked 'prompt' field: {record!r}"
+        )
+        assert "prompt_preview" not in record
+        # But length should be there for ops visibility.
+        assert record.get("prompt_len") == len(secret_prompt)
+        # ``args`` is part of the base-runner contract — claude override
+        # should mirror it so subprocess invocation is visible.
+        assert "args" in record
+        # The literal prompt sentinel must not appear anywhere in the record.
+        assert sentinel not in str(record), (
+            f"runner.start INFO leaked prompt sentinel: {record!r}"
+        )
+        # And `env -i KEY=VAL` pairs in args must be redacted (#361) so
+        # secrets passed via env-wrap don't surface even when ``args`` is
+        # logged. Spot-check on a known-redacted name from the env policy.
+        args_str = str(record.get("args"))
+        if "BWS_ACCESS_TOKEN" in args_str:
+            assert "BWS_ACCESS_TOKEN=***" in args_str, (
+                f"env -i pair should be redacted: {args_str}"
+            )
+
+
+@pytest.mark.anyio
+async def test_runner_start_redacts_legacy_mode_prompt_in_args(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """#478: in legacy ``-p <prompt>`` mode (no permission_mode set), the
+    prompt sits as the last argv element after ``--``. The runner.start INFO
+    log must redact at the ``--`` boundary so prompt content still doesn't
+    reach INFO. Covers the path where _effective_permission_mode() is None.
+    """
+    from structlog.testing import capture_logs
+
+    class _BoomManager:
+        async def __aenter__(self) -> object:
+            raise RuntimeError("stop_after_log")
+
+        async def __aexit__(self, exc_type, exc, tb) -> None:
+            return None
+
+    def fake_manage_subprocess(*args: object, **kwargs: object) -> _BoomManager:
+        _ = args, kwargs
+        return _BoomManager()
+
+    monkeypatch.setattr(claude_runner, "manage_subprocess", fake_manage_subprocess)
+
+    # No permission_mode → legacy ``-p`` path, prompt lands in argv.
+    runner = ClaudeRunner(claude_cmd="claude")
+    sentinel = "ZAPHOD-LEGACY-SECRET-XYZZY-9876"
+    secret_prompt = f"top-secret legacy: {sentinel} run the task"
+
+    with capture_logs() as logs, contextlib.suppress(RuntimeError):
+        async for _evt in runner.run_impl(secret_prompt, None):
+            pass
+
+    start_events = [r for r in logs if r.get("event") == "runner.start"]
+    assert start_events, "runner.start INFO event must fire"
+    for record in start_events:
+        # The literal prompt sentinel must NOT leak through args.
+        assert sentinel not in str(record), (
+            f"runner.start INFO leaked prompt sentinel via legacy args: {record!r}"
+        )
+        args = record.get("args") or []
+        # Legacy mode appends ``--`` then the prompt; we replace the prompt
+        # with a placeholder string so reviewers can still tell the run was
+        # in legacy mode without exposing prompt content.
+        assert "--" in args
+        assert "<prompt redacted>" in args
+
+
 # ---------------------------------------------------------------------------
 # #347 — background-task tracking (Monitor / Bash-bg / Agent-bg /
 # ScheduleWakeup / RemoteTrigger)
@@ -316,6 +437,58 @@ def test_schedule_wakeup_tracked_with_deadline() -> None:
     assert "toolu_W1" in state.live_wakeups
 
 
+def test_schedule_wakeup_reads_delaySeconds_field() -> None:
+    """#481: real Claude Code stream-json emits ``delaySeconds`` (#289).
+
+    Previous code only read ``delay_ms``/``timeout_ms`` so production
+    deadlines fell to 0.0 (countdown rendering broken). Verify the new
+    code path: a 60s wakeup yields a ``deadline`` ~60s in the future.
+    """
+    import time
+
+    state = ClaudeStreamState()
+    before = time.monotonic()
+    translate_claude_event(
+        _decode_event(
+            _make_tool_use_event("ScheduleWakeup", "toolu_W2", {"delaySeconds": 60})
+        ),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    after = time.monotonic()
+    deadline = state.live_wakeups["toolu_W2"]
+    # 60s wakeup → deadline between (before + 60) and (after + 60).
+    assert before + 60.0 <= deadline <= after + 60.0
+
+
+def test_schedule_wakeup_delay_ms_fallback_still_works() -> None:
+    """Backward-compat: delay_ms fallback still produces a valid deadline."""
+    import time
+
+    state = ClaudeStreamState()
+    before = time.monotonic()
+    translate_claude_event(
+        _decode_event(
+            _make_tool_use_event("ScheduleWakeup", "toolu_W3", {"delay_ms": 30_000})
+        ),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    deadline = state.live_wakeups["toolu_W3"]
+    # 30s wakeup via delay_ms fallback.
+    assert before + 30.0 <= deadline <= time.monotonic() + 30.0
+
+
+def test_post_result_closing_state_initial_values() -> None:
+    """#470: ClaudeStreamState carries the new closing-message signal fields."""
+    state = ClaudeStreamState()
+    assert state.post_result_closed_at is None
+    assert state.post_result_idle_minutes == 0.0
+    assert state.post_result_closing_sent is False
+
+
 def test_remote_trigger_tracked_as_set_member() -> None:
     state = ClaudeStreamState()
     translate_claude_event(
@@ -920,6 +1093,361 @@ def test_translate_thinking_block() -> None:
     assert events[0].ok is True
 
 
+# ---------------------------------------------------------------------------
+# #489 — server_tool_use + advisor_tool_result content blocks (regression)
+# ---------------------------------------------------------------------------
+
+
+def test_translate_server_tool_use_block() -> None:
+    """server_tool_use shares the tool_use translation path: emits an
+    action_started, populates state.pending_actions, and stamps
+    state.last_tool_use_id. Regression for #489 — previously msgspec
+    rejected the whole JSONL line and the event was silently dropped."""
+    state = ClaudeStreamState()
+    event = {
+        "type": "assistant",
+        "message": {
+            "id": "msg_1",
+            "content": [
+                {
+                    "type": "server_tool_use",
+                    "id": "stu_01",
+                    "name": "web_search",
+                    "input": {"query": "untether telegram"},
+                }
+            ],
+        },
+    }
+
+    events = translate_claude_event(
+        _decode_event(event),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+
+    assert len(events) == 1
+    assert isinstance(events[0], ActionEvent)
+    assert events[0].phase == "started"
+    assert events[0].action.id == "stu_01"
+    assert "stu_01" in state.pending_actions
+    assert state.last_tool_use_id == "stu_01"
+
+
+def test_translate_exitplanmode_captures_plan_body() -> None:
+    """#508 — translating a tool_use(name='ExitPlanMode', input.plan='...')
+    captures the plan body onto state.last_exitplanmode_plan so the bridge
+    can re-emit it in the final answer if the post-approval result is
+    brief.  Regression for the live research-task short-final-message bug.
+    """
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-508")
+    plan_body = (
+        "Findings:\n"
+        "- File X has bug Y at line 42\n"
+        "- File Z is unaffected\n"
+        "- Recommend fix A\n"
+    )
+    event = {
+        "type": "assistant",
+        "message": {
+            "id": "msg_1",
+            "content": [
+                {
+                    "type": "tool_use",
+                    "id": "tu_epm_1",
+                    "name": "ExitPlanMode",
+                    "input": {"plan": plan_body},
+                }
+            ],
+        },
+    }
+
+    translate_claude_event(
+        _decode_event(event),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+
+    assert state.last_exitplanmode_plan == plan_body
+
+
+def test_translate_exitplanmode_ignores_empty_plan_body() -> None:
+    """#508 — empty/whitespace-only plan bodies are NOT captured. Avoids
+    overwriting a real prior value with an inadvertent retry/empty call."""
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-508")
+    state.last_exitplanmode_plan = "earlier plan body"
+    event = {
+        "type": "assistant",
+        "message": {
+            "id": "msg_2",
+            "content": [
+                {
+                    "type": "tool_use",
+                    "id": "tu_epm_2",
+                    "name": "ExitPlanMode",
+                    "input": {"plan": "   "},
+                }
+            ],
+        },
+    }
+
+    translate_claude_event(
+        _decode_event(event),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+
+    assert state.last_exitplanmode_plan == "earlier plan body"
+
+
+def test_translate_result_prepends_exitplanmode_plan_into_answer() -> None:
+    """#510: the ExitPlanMode plan body re-emit happens HERE on the per-stream
+    result path (claude.py), not in runner_bridge against the singleton
+    runner.current_stream. Verifies the prepend uses state.last_exitplanmode_plan
+    from the SAME state instance that received the result event.
+    """
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-510")
+    state.last_exitplanmode_plan = "- Finding 1\n- Finding 2\n- Recommend X"
+    short_post_approval_result = "Plan approved — see file."
+
+    event = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=2,
+        session_id="sess-510",
+        result=short_post_approval_result,
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    completed = [evt for evt in events if isinstance(evt, CompletedEvent)]
+    assert len(completed) == 1
+    answer = completed[0].answer
+    assert "📋 Plan (approved):" in answer
+    assert "- Finding 1" in answer
+    assert short_post_approval_result in answer
+    # Plan body comes before the brief post-approval text
+    assert answer.index("- Finding 1") < answer.index(short_post_approval_result)
+
+
+def test_concurrent_states_do_not_leak_exitplanmode_plan_bodies() -> None:
+    """#510 regression — the live bug. Two concurrent Claude sessions
+    each had their own ClaudeStreamState. Previously the bridge read the
+    plan body from ``runner.current_stream`` (a shared singleton on the
+    runner), which was overwritten when either session re-entered
+    run_impl. The fix routes the prepend through the per-stream
+    translate path, so each state can ONLY ever read its own plan body.
+
+    Models the production incident: chat A captured "PLAN — CHANNELO
+    TUNNEL" on its state, chat B was completing a different task with
+    its own short answer — chat B's CompletedEvent must NOT contain
+    chat A's plan body.
+    """
+    state_a = ClaudeStreamState()
+    state_a.factory._resume = ResumeToken(engine="claude", value="sess-A")
+    state_a.last_exitplanmode_plan = "PLAN — CHANNELO TUNNEL secret content"
+
+    state_b = ClaudeStreamState()
+    state_b.factory._resume = ResumeToken(engine="claude", value="sess-B")
+    # state_b has its own (smaller) plan body — different content
+    state_b.last_exitplanmode_plan = "PLAN — legal-DB handover"
+
+    # Session B completes with a brief post-approval result.
+    event_b = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=2,
+        session_id="sess-B",
+        result="done",
+    )
+    events_b = translate_claude_event(
+        event_b,
+        title="claude",
+        state=state_b,
+        factory=state_b.factory,
+    )
+    completed_b = next(evt for evt in events_b if isinstance(evt, CompletedEvent))
+
+    # Session B's answer must only contain its own plan body.
+    assert "PLAN — legal-DB handover" in completed_b.answer
+    assert "CHANNELO TUNNEL" not in completed_b.answer
+    assert "secret content" not in completed_b.answer
+
+
+def test_translate_result_error_does_not_prepend_plan(monkeypatch) -> None:
+    """#510: only the OK path prepends. Errored result paths flow into
+    _extract_error and must not also receive a plan-body prepend.
+    """
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-510-err")
+    state.last_exitplanmode_plan = "- Should not appear"
+
+    event = claude_schema.StreamResultMessage(
+        subtype="error_during_execution",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=True,
+        num_turns=1,
+        session_id="sess-510-err",
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    completed = next(evt for evt in events if isinstance(evt, CompletedEvent))
+    assert "📋 Plan (approved):" not in (completed.answer or "")
+    assert "- Should not appear" not in (completed.answer or "")
+
+
+def test_translate_result_skips_prepend_when_answer_substantive() -> None:
+    """#515: when the post-approval text is already a substantive
+    CLI-style summary (≥ ``_PREPEND_LENGTH_GATE`` chars), Layer E must
+    NOT prepend the plan body. Without this gate the rc11/rc12 fix
+    concatenated plan body + paraphrased summary on every well-behaved
+    run, producing 25k-42k char Telegram finals on staging.
+    """
+    from untether.runners.claude import _PREPEND_LENGTH_GATE
+
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-515")
+    state.last_exitplanmode_plan = "- Plan finding 1\n- Plan finding 2"
+
+    # A real CLI-style summary, just above the gate. Claude paraphrases
+    # rather than literal-copies, so the substring check would fail —
+    # the length gate is what stops the double-ship.
+    summary = (
+        "Investigation complete. Here is what I found:\n\n"
+        "- Module X had a regression introduced in commit abc123\n"
+        "- The root cause was a missing null guard in the parser\n"
+        "- Rolled back the change and added a regression test\n"
+        "- Next step: backfill the affected rows on Monday morning\n\n"
+        "Decisions made: kept the legacy code path for one more release cycle\n"
+        "to give downstream consumers time to migrate; full removal scheduled\n"
+        "for the next minor version once telemetry confirms zero active\n"
+        "callers. Telegram message size budget respected (under 1500 chars).\n\n"
+        "Next steps: open a follow-up issue to track the backfill timeline,\n"
+        "send a heads-up in the team channel about the rollback, and re-run\n"
+        "the daily-audit cron tomorrow morning to confirm the regression has\n"
+        "cleared the verification window before closing this thread.\n"
+    )
+    assert len(summary) >= _PREPEND_LENGTH_GATE
+
+    event = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=2,
+        session_id="sess-515",
+        result=summary,
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    completed = next(evt for evt in events if isinstance(evt, CompletedEvent))
+    assert completed.answer == summary
+    assert "📋 Plan (approved):" not in completed.answer
+
+
+def test_translate_result_caps_long_plan_body_when_prepending() -> None:
+    """#515: when Layer E does fire (short post-approval answer), an
+    over-long captured plan body must be truncated to
+    ``_PREPEND_BODY_CAP`` chars + a truncation marker. Without this cap
+    a 30k-char plan body still ships a 30k-char Telegram final even
+    after the length gate is added.
+    """
+    from untether.runners.claude import _PREPEND_BODY_CAP
+
+    state = ClaudeStreamState()
+    state.factory._resume = ResumeToken(engine="claude", value="sess-515-cap")
+    state.last_exitplanmode_plan = "x" * (_PREPEND_BODY_CAP + 2000)
+
+    event = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=2,
+        session_id="sess-515-cap",
+        result="ok",
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    completed = next(evt for evt in events if isinstance(evt, CompletedEvent))
+    assert "📋 Plan (approved):" in completed.answer
+    assert "plan truncated" in completed.answer
+    # Final answer should not contain the full 3500-char plan body.
+    assert "x" * (_PREPEND_BODY_CAP + 100) not in completed.answer
+
+
+def test_translate_advisor_tool_result_block() -> None:
+    """advisor_tool_result shares the tool_result translation path: emits an
+    action_completed and pops the matching entry from state.pending_actions.
+    Regression for #489."""
+    state = ClaudeStreamState()
+    # Inject a pending action keyed on the tool_use_id (mirrors what would
+    # have been registered by the prior server_tool_use / tool_use call).
+    from untether.model import Action
+
+    state.pending_actions["adv_01"] = Action(
+        id="adv_01",
+        kind="tool",
+        title="advisor",
+        detail={},
+    )
+
+    event = {
+        "type": "user",
+        "message": {
+            "id": "msg_r",
+            "content": [
+                {
+                    "type": "advisor_tool_result",
+                    "tool_use_id": "adv_01",
+                    "content": "Reviewer said: looks good.",
+                    "is_error": False,
+                }
+            ],
+        },
+    }
+
+    events = translate_claude_event(
+        _decode_event(event),
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+
+    assert any(
+        isinstance(e, ActionEvent)
+        and e.phase == "completed"
+        and e.action.id == "adv_01"
+        for e in events
+    )
+    assert "adv_01" not in state.pending_actions
+
+
 @pytest.mark.anyio
 async def test_run_serializes_same_session() -> None:
     runner = ClaudeRunner(claude_cmd="claude")
@@ -1250,20 +1778,156 @@ def test_extract_error_with_result_text() -> None:
 
 
 # ===========================================================================
-# #361 — runtime env audit hook on system.init
+# #438 — Stream idle timeout Type-A vs Type-B classification
 # ===========================================================================
 
 
-def test_env_audit_emits_warning_on_leaked_var(monkeypatch) -> None:
-    """`_maybe_audit_env` warns once per leaked name when /proc shows it."""
-    from structlog.testing import capture_logs
-
-    from untether.runners.claude import _maybe_audit_env
+def test_extract_error_type_a_stream_idle_timeout() -> None:
+    """Mid-generation stall: num_turns >= 1 and duration_api_ms > 0.
+    Surface as Type A with hint to raise the timeout."""
+    from untether.runners.claude import _extract_error
 
-    monkeypatch.setattr(
-        claude_runner, "audit_proc_env", lambda pid, **kw: ["BWS_ACCESS_TOKEN"]
+    event = claude_schema.StreamResultMessage(
+        subtype="error_during_execution",
+        duration_ms=635000,
+        duration_api_ms=261086,
+        is_error=True,
+        num_turns=19,
+        session_id="36693744aaaa0000",
+        result="API Error: Stream idle timeout - partial response received",
     )
-    monkeypatch.setattr(claude_runner, "load_settings_if_exists", lambda: None)
+    result = _extract_error(event, resumed=False)
+    assert result is not None
+    assert "Type A" in result
+    assert "Mid-generation" in result
+    assert "claude_stream_idle_timeout_ms" in result
+    # Type-B language must NOT appear.
+    assert "Type B" not in result
+    assert "no bytes" not in result.lower()
+
+
+def test_extract_error_type_b_stream_idle_timeout_zero_bytes() -> None:
+    """Cold-start zero-byte stall: num_turns <= 1 and duration_api_ms == 0.
+    Surface as Type B and tell the user raising the timeout will NOT help."""
+    from untether.runners.claude import _extract_error
+
+    event = claude_schema.StreamResultMessage(
+        subtype="error_during_execution",
+        duration_ms=350000,
+        duration_api_ms=0,
+        is_error=True,
+        num_turns=1,
+        session_id="24960feabbbb0000",
+        result="API Error: Stream idle timeout - partial response received",
+    )
+    result = _extract_error(event, resumed=True)
+    assert result is not None
+    assert "Type B" in result
+    assert "Cold-start" in result
+    assert "no bytes" in result
+    assert "will NOT help" in result
+    # Type-A language must NOT appear.
+    assert "Type A" not in result
+
+
+def test_extract_error_unrelated_failure_no_classification() -> None:
+    """Non-stall errors must not gain a Type-A/B annotation."""
+    from untether.runners.claude import _extract_error
+
+    event = claude_schema.StreamResultMessage(
+        subtype="error_during_execution",
+        duration_ms=5000,
+        duration_api_ms=3000,
+        is_error=True,
+        num_turns=2,
+        session_id="abcdef1234567890",
+        result="Tool execution failed with code 1",
+    )
+    result = _extract_error(event, resumed=False)
+    assert result is not None
+    assert "Type A" not in result
+    assert "Type B" not in result
+    assert "Tool execution failed" in result
+
+
+# ===========================================================================
+# #438 — claude_stream_idle_timeout_ms config knob
+# ===========================================================================
+
+
+def test_env_stream_idle_timeout_configured_value(monkeypatch, tmp_path) -> None:
+    """[watchdog] claude_stream_idle_timeout_ms in untether.toml is honoured."""
+    monkeypatch.delenv("CLAUDE_STREAM_IDLE_TIMEOUT_MS", raising=False)
+
+    from untether import runners as untether_runners
+    from untether.settings import (
+        TelegramTransportSettings,
+        UntetherSettings,
+        WatchdogSettings,
+    )
+
+    settings = UntetherSettings(
+        transport="telegram",
+        transports={
+            "telegram": TelegramTransportSettings(
+                bot_token="test:token",
+                chat_id=12345,
+                allow_any_user=True,
+            )
+        },
+        watchdog=WatchdogSettings(claude_stream_idle_timeout_ms=600_000),
+    )
+
+    monkeypatch.setattr(
+        untether_runners.claude,
+        "load_settings_if_exists",
+        lambda: (settings, tmp_path / "untether.toml"),
+    )
+
+    runner = ClaudeRunner(claude_cmd="claude")
+    env = runner.env(state=None)
+    assert env is not None
+    assert env["CLAUDE_STREAM_IDLE_TIMEOUT_MS"] == "600000"
+
+
+def test_env_stream_idle_timeout_settings_load_failure_falls_back(
+    monkeypatch,
+) -> None:
+    """If settings can't load, the hardcoded 300000 default still applies."""
+    monkeypatch.delenv("CLAUDE_STREAM_IDLE_TIMEOUT_MS", raising=False)
+
+    from untether import runners as untether_runners
+
+    def _boom():
+        raise RuntimeError("settings load failed")
+
+    monkeypatch.setattr(
+        untether_runners.claude,
+        "load_settings_if_exists",
+        _boom,
+    )
+
+    runner = ClaudeRunner(claude_cmd="claude")
+    env = runner.env(state=None)
+    assert env is not None
+    assert env["CLAUDE_STREAM_IDLE_TIMEOUT_MS"] == "300000"
+
+
+# ===========================================================================
+# #361 — runtime env audit hook on system.init
+# ===========================================================================
+
+
+def test_env_audit_emits_warning_on_leaked_var(monkeypatch) -> None:
+    """`_maybe_audit_env` warns once per leaked name when /proc shows it."""
+    from structlog.testing import capture_logs
+
+    from untether.runners.claude import _maybe_audit_env
+
+    monkeypatch.setattr(
+        claude_runner, "audit_proc_env", lambda pid, **kw: ["BWS_ACCESS_TOKEN"]
+    )
+    monkeypatch.setattr(claude_runner, "load_settings_if_exists", lambda: None)
 
     state = ClaudeStreamState()
     state.pid = 4242
@@ -1429,3 +2093,838 @@ def test_redact_env_i_args_passthrough_when_not_env_wrapped() -> None:
 
     cmd = ["claude", "--output-format", "stream-json", "--effort", "xhigh"]
     assert redact_env_i_args(cmd) == cmd
+
+
+# ── #333 — post-result idle timeout & turn-complete UX signal ─────────────
+
+
+def test_translate_result_arms_post_result_idle_timer() -> None:
+    """A `result` event sets `state.result_received_at` for the watchdog."""
+    state = ClaudeStreamState()
+    assert state.result_received_at is None
+
+    event = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=1,
+        session_id="post-result-timer-session",
+        result="done",
+    )
+    translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    assert state.result_received_at is not None
+    assert state.result_received_at > 0
+
+
+def test_translate_result_emits_turn_complete_meta() -> None:
+    """Successful result emits supplementary StartedEvent with complete hint."""
+    state = ClaudeStreamState()
+    event = claude_schema.StreamResultMessage(
+        subtype="success",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=False,
+        num_turns=1,
+        session_id="turn-complete-session",
+        result="done",
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    started = [evt for evt in events if isinstance(evt, StartedEvent)]
+    completed = [evt for evt in events if isinstance(evt, CompletedEvent)]
+    assert len(started) == 1
+    assert len(completed) == 1
+    assert started[0].meta == {"complete": "✓ turn complete"}
+    # CompletedEvent must remain the LAST event for the 3-event contract.
+    assert events[-1] is completed[0]
+
+
+def test_translate_result_skips_complete_meta_on_error() -> None:
+    """Errored result does NOT add the turn-complete meta hint."""
+    state = ClaudeStreamState()
+    event = claude_schema.StreamResultMessage(
+        subtype="error_during_execution",
+        duration_ms=100,
+        duration_api_ms=50,
+        is_error=True,
+        num_turns=1,
+        session_id="errored-session",
+    )
+    events = translate_claude_event(
+        event,
+        title="claude",
+        state=state,
+        factory=state.factory,
+    )
+    started = [evt for evt in events if isinstance(evt, StartedEvent)]
+    completed = [evt for evt in events if isinstance(evt, CompletedEvent)]
+    assert len(started) == 0  # no supplementary started for failures
+    assert len(completed) == 1
+    assert completed[0].ok is False
+
+
+@pytest.mark.anyio
+async def test_post_result_idle_watchdog_fires_when_clean(monkeypatch) -> None:
+    """Past the timeout with no pending approvals → stdin is closed."""
+    import anyio
+
+    from untether.runners.claude import (
+        _PENDING_ASK_REQUESTS,
+        _REQUEST_TO_SESSION,
+        ClaudeRunner,
+    )
+
+    # Ensure registries are clean.
+    _REQUEST_TO_SESSION.clear()
+    _PENDING_ASK_REQUESTS.clear()
+
+    runner = ClaudeRunner(claude_cmd="claude")
+    state = ClaudeStreamState()
+    # Seed the factory with a resume token so the watchdog can find the sid.
+    state.factory.started(
+        ResumeToken(engine="claude", value="watchdog-clean-session"),
+    )
+    # Arm the timer: pretend the result event landed 1000s ago.
+    state.result_received_at = time.monotonic() - 1000.0
+
+    closed = anyio.Event()
+
+    class FakeStdin:
+        async def aclose(self) -> None:
+            closed.set()
+
+    fake_stdin = FakeStdin()
+    reader_done = anyio.Event()
+
+    # Patch sleep so the watchdog ticks immediately.
+    real_sleep = anyio.sleep
+
+    async def fast_sleep(s: float) -> None:
+        await real_sleep(0)
+
+    monkeypatch.setattr("untether.runners.claude.anyio.sleep", fast_sleep)
+
+    class _StubLogger:
+        def info(self, *a, **k) -> None:
+            pass
+
+        def warning(self, *a, **k) -> None:
+            pass
+
+        def debug(self, *a, **k) -> None:
+            pass
+
+    async with anyio.create_task_group() as tg:
+        tg.start_soon(
+            runner._post_result_idle_watchdog,
+            state,
+            fake_stdin,
+            reader_done,
+            _StubLogger(),
+            60.0,
+        )
+        # Give the task one tick to detect the expired timer + close.
+        with anyio.move_on_after(2.0):
+            await closed.wait()
+        tg.cancel_scope.cancel()
+
+    assert closed.is_set(), "watchdog should have closed stdin"
+
+
+@pytest.mark.anyio
+async def test_post_result_idle_watchdog_defers_when_pending_approval(
+    monkeypatch,
+) -> None:
+    """An in-flight approval suppresses the close, re-arming the timer."""
+    import anyio
+
+    from untether.runners.claude import (
+        _PENDING_ASK_REQUESTS,
+        _REQUEST_TO_SESSION,
+        ClaudeRunner,
+    )
+
+    sid = "watchdog-deferred-session"
+    _REQUEST_TO_SESSION.clear()
+    _PENDING_ASK_REQUESTS.clear()
+    _REQUEST_TO_SESSION["req_pending"] = sid
+    try:
+        runner = ClaudeRunner(claude_cmd="claude")
+        state = ClaudeStreamState()
+        state.factory.started(ResumeToken(engine="claude", value=sid))
+        original_armed = time.monotonic() - 1000.0
+        state.result_received_at = original_armed
+
+        closed = anyio.Event()
+
+        class FakeStdin:
+            async def aclose(self) -> None:
+                closed.set()
+
+        real_sleep = anyio.sleep
+
+        async def fast_sleep(s: float) -> None:
+            await real_sleep(0)
+
+        monkeypatch.setattr("untether.runners.claude.anyio.sleep", fast_sleep)
+
+        class _StubLogger:
+            def info(self, *a, **k) -> None:
+                pass
+
+            def warning(self, *a, **k) -> None:
+                pass
+
+            def debug(self, *a, **k) -> None:
+                pass
+
+        reader_done = anyio.Event()
+        async with anyio.create_task_group() as tg:
+            tg.start_soon(
+                runner._post_result_idle_watchdog,
+                state,
+                FakeStdin(),
+                reader_done,
+                _StubLogger(),
+                60.0,
+            )
+            # Let the watchdog tick a few times, then signal reader_done so
+            # the loop exits without our needing to wait.
+            for _ in range(5):
+                await real_sleep(0)
+            reader_done.set()
+            tg.cancel_scope.cancel()
+
+        assert not closed.is_set(), (
+            "watchdog must not close stdin while approval pending"
+        )
+        # The timer was re-armed (pushed forward), so result_received_at
+        # should now be more recent than the original arming.
+        assert state.result_received_at is not None
+        assert state.result_received_at > original_armed
+    finally:
+        _REQUEST_TO_SESSION.pop("req_pending", None)
+
+
+# ───── #507 — dead ScheduleWakeup outside /loop shortcut ───────────────
+
+
+@pytest.mark.anyio
+async def test_dead_schedule_wakeup_shortens_post_result_timeout(
+    monkeypatch,
+) -> None:
+    """When ScheduleWakeup armed during the run AND /loop is OFF for the
+    chat, ``_post_result_idle_watchdog`` cuts its effective timeout to
+    ``max_armed_delay + 60s`` so the session closes within delay+grace
+    instead of waiting the default 600s. Validates the fix for #507.
+    """
+    import anyio
+
+    from untether.runners.claude import (
+        _PENDING_ASK_REQUESTS,
+        _REQUEST_TO_SESSION,
+        ClaudeRunner,
+    )
+    from untether.runners.run_options import EngineRunOptions, apply_run_options
+    from untether.utils.paths import set_run_channel_id
+
+    _REQUEST_TO_SESSION.clear()
+    _PENDING_ASK_REQUESTS.clear()
+
+    runner = ClaudeRunner(claude_cmd="claude")
+    state = ClaudeStreamState()
+    state.factory.started(
+        ResumeToken(engine="claude", value="watchdog-dead-wakeup-session"),
+    )
+    # ScheduleWakeup armed with delaySeconds=75 → arm_delay dict tracks 75.0.
+    # We only need the parallel arm_delay dict populated for the shortcut
+    # check; the deadline value doesn't affect the test.
+    state.live_wakeups["toolu_W"] = time.monotonic() + 75.0
+    state.live_wakeups_arm_delay["toolu_W"] = 75.0
+    # Pretend the result event landed 200s ago — past the dead-wakeup
+    # effective_timeout (75 + 60 = 135s) but still well below the default
+    # 600s timeout.
+    state.result_received_at = time.monotonic() - 200.0
+
+    closed = anyio.Event()
+
+    class FakeStdin:
+        async def aclose(self) -> None:
+            closed.set()
+
+    fake_stdin = FakeStdin()
+    reader_done = anyio.Event()
+
+    real_sleep = anyio.sleep
+
+    async def fast_sleep(s: float) -> None:
+        await real_sleep(0)
+
+    monkeypatch.setattr("untether.runners.claude.anyio.sleep", fast_sleep)
+
+    captured_logs: list[dict] = []
+
+    class _StubLogger:
+        def info(self, event: str = "", **kwargs) -> None:
+            captured_logs.append({"event": event, **kwargs})
+
+        def warning(self, *a, **k) -> None:
+            pass
+
+        def debug(self, *a, **k) -> None:
+            pass
+
+    # /loop OFF for the chat (default). Set a chat_id so the shortcut
+    # finds it.
+    token = set_run_channel_id(12345)
+    try:
+        with apply_run_options(EngineRunOptions(loop_enabled=False)):
+            async with anyio.create_task_group() as tg:
+                tg.start_soon(
+                    runner._post_result_idle_watchdog,
+                    state,
+                    fake_stdin,
+                    reader_done,
+                    _StubLogger(),
+                    600.0,  # default timeout — shortcut should cut to 135s
+                )
+                with anyio.move_on_after(2.0):
+                    await closed.wait()
+                tg.cancel_scope.cancel()
+    finally:
+        from untether.utils.paths import reset_run_channel_id
+
+        reset_run_channel_id(token)
+
+    assert closed.is_set(), "watchdog should have closed stdin"
+    # Verify the closing log marked dead_wakeup=True with the shortened
+    # effective_timeout.
+    closing = next(
+        (
+            lg
+            for lg in captured_logs
+            if lg["event"] == "claude.post_result_idle.closing_stdin"
+        ),
+        None,
+    )
+    assert closing is not None
+    assert closing["dead_wakeup"] is True
+    assert closing["effective_timeout_s"] == 135.0
+
+
+@pytest.mark.anyio
+async def test_active_loop_preserves_default_post_result_timeout(
+    monkeypatch,
+) -> None:
+    """When /loop is ON for the chat, the dead-wakeup shortcut must NOT
+    apply — the wakeup is legitimate background work. The watchdog should
+    use the full default timeout.
+    """
+    import anyio
+
+    from untether.runners.claude import (
+        _PENDING_ASK_REQUESTS,
+        _REQUEST_TO_SESSION,
+        ClaudeRunner,
+    )
+    from untether.runners.run_options import EngineRunOptions, apply_run_options
+    from untether.utils.paths import set_run_channel_id
+
+    _REQUEST_TO_SESSION.clear()
+    _PENDING_ASK_REQUESTS.clear()
+
+    runner = ClaudeRunner(claude_cmd="claude")
+    state = ClaudeStreamState()
+    state.factory.started(
+        ResumeToken(engine="claude", value="watchdog-loop-on-session"),
+    )
+    state.live_wakeups["toolu_W"] = time.monotonic() + 75.0
+    state.live_wakeups_arm_delay["toolu_W"] = 75.0
+    # Pretend result landed 200s ago — past the dead-wakeup shortcut
+    # threshold (135s), but well below the 600s default timeout. With
+    # /loop ON the watchdog should NOT close stdin yet.
+    state.result_received_at = time.monotonic() - 200.0
+
+    closed = anyio.Event()
+
+    class FakeStdin:
+        async def aclose(self) -> None:
+            closed.set()
+
+    fake_stdin = FakeStdin()
+    reader_done = anyio.Event()
+
+    real_sleep = anyio.sleep
+
+    async def fast_sleep(s: float) -> None:
+        await real_sleep(0)
+
+    monkeypatch.setattr("untether.runners.claude.anyio.sleep", fast_sleep)
+
+    class _StubLogger:
+        def info(self, *a, **k) -> None:
+            pass
+
+        def warning(self, *a, **k) -> None:
+            pass
+
+        def debug(self, *a, **k) -> None:
+            pass
+
+    token = set_run_channel_id(12345)
+    try:
+        with apply_run_options(EngineRunOptions(loop_enabled=True)):
+            async with anyio.create_task_group() as tg:
+                tg.start_soon(
+                    runner._post_result_idle_watchdog,
+                    state,
+                    fake_stdin,
+                    reader_done,
+                    _StubLogger(),
+                    600.0,
+                )
+                # Tick a few times, then signal reader_done.
+                for _ in range(10):
+                    await real_sleep(0)
+                reader_done.set()
+                tg.cancel_scope.cancel()
+    finally:
+        from untether.utils.paths import reset_run_channel_id
+
+        reset_run_channel_id(token)
+
+    assert not closed.is_set(), "with /loop ON, dead-wakeup shortcut must not fire"
+
+
+def test_meta_line_renders_turn_complete_marker() -> None:
+    """format_meta_line includes the `complete` hint when set on meta."""
+    from untether.markdown import format_meta_line
+
+    line = format_meta_line({"model": "sonnet", "complete": "✓ turn complete"})
+    assert line is not None
+    assert "✓ turn complete" in line
+
+
+def test_meta_line_omits_complete_when_absent() -> None:
+    """Absence of the `complete` key keeps the legacy footer shape."""
+    from untether.markdown import format_meta_line
+
+    line = format_meta_line({"model": "sonnet"})
+    assert line is not None
+    assert "✓ turn complete" not in line
+
+
+def test_is_session_alive_reads_session_stdin_registry() -> None:
+    """is_session_alive (#289) returns True iff session_id is in _SESSION_STDIN."""
+    from untether.runners.claude import _SESSION_STDIN, is_session_alive
+
+    sid = "test-session-289-alive"
+    try:
+        assert is_session_alive(sid) is False
+        _SESSION_STDIN[sid] = object()  # any sentinel is enough — we test membership
+        assert is_session_alive(sid) is True
+    finally:
+        _SESSION_STDIN.pop(sid, None)
+
+
+def test_is_session_alive_unknown_session_returns_false() -> None:
+    """Sessions never registered are not alive."""
+    from untether.runners.claude import is_session_alive
+
+    assert is_session_alive("session-that-was-never-spawned") is False
+
+
+# ───── #289 — /loop and ScheduleWakeup observation ─────────────────────
+
+
+def _seed_state_for_loop_observation(
+    state: ClaudeStreamState, *, session_id: str = "sess-289"
+) -> None:
+    """Helper: set state.factory._resume so ``_observe_loop_tool_use`` can
+    read the session_id without a full system.init flow."""
+    state.factory._resume = ResumeToken(engine="claude", value=session_id)
+    state.first_user_message_text = "user typed /loop check the deploy"
+
+
+@pytest.mark.anyio
+class TestLoopObservation:
+    """Cover the new ``_observe_loop_tool_use`` /
+    ``_observe_loop_tool_result`` helpers and the ``_loop_enabled_for_chat``
+    gate.  Mirrors ``test_loop_scheduler.py`` cleanup conventions.
+    """
+
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        from untether import loop_scheduler
+
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    @pytest.fixture
+    def _enable_loop(self):
+        """Toggle Loop mode ON via the per-chat run-options contextvar so
+        the master gate inside the observer doesn't short-circuit."""
+        from untether.runners.run_options import (
+            EngineRunOptions,
+            apply_run_options,
+        )
+
+        with apply_run_options(EngineRunOptions(loop_enabled=True)):
+            yield
+
+    @pytest.fixture
+    def _disable_loop(self):
+        """Toggle Loop mode OFF explicitly."""
+        from untether.runners.run_options import (
+            EngineRunOptions,
+            apply_run_options,
+        )
+
+        with apply_run_options(EngineRunOptions(loop_enabled=False)):
+            yield
+
+    @pytest.fixture
+    def _set_chat(self):
+        """Push a chat_id into the run-context contextvar."""
+        from untether.utils.paths import (
+            reset_run_channel_id,
+            set_run_channel_id,
+        )
+
+        token = set_run_channel_id(7777)
+        try:
+            yield 7777
+        finally:
+            reset_run_channel_id(token)
+
+    @pytest.fixture
+    async def _installed_scheduler(self):
+        """Install loop_scheduler so observers can call register_*."""
+        from untether import loop_scheduler
+
+        async def _noop(*args, **kwargs):
+            return None
+
+        class _Transport:
+            async def send(self, **_):
+                return None
+
+            async def edit(self, **_):
+                return None
+
+            async def delete(self, _ref):
+                return None
+
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop, _Transport(), 1)
+            try:
+                yield
+            finally:
+                tg.cancel_scope.cancel()
+
+    @pytest.mark.usefixtures("_enable_loop", "_installed_scheduler")
+    async def test_observer_skipped_when_chat_id_unset(self):
+        """Without ``set_run_channel_id`` the observer must no-op."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_C1",
+                    {"cron": "* * * * *", "prompt": "x", "recurring": True},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 0
+
+    @pytest.mark.usefixtures("_disable_loop", "_set_chat", "_installed_scheduler")
+    async def test_observer_skipped_when_toggle_off(self):
+        """Loop mode OFF → no registration."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_C2",
+                    {"cron": "* * * * *", "prompt": "ping", "recurring": True},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 0
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_cron_create_registers_when_enabled(self):
+        """CronCreate with toggle ON registers a recurring entry."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state, session_id="sess-cron-on")
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_C3",
+                    {
+                        "cron": "*/5 * * * *",
+                        "prompt": "check the deploy",
+                        "recurring": True,
+                    },
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 1
+        pending = loop_scheduler.pending_for_chat(7777)
+        assert len(pending) == 1
+        assert pending[0].cron_expression == "*/5 * * * *"
+        assert pending[0].prompt == "check the deploy"
+        assert pending[0].recurring is True
+        assert pending[0].resume_token == "sess-cron-on"
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_cron_create_uses_cron_field_not_cron_expression(self):
+        """Probe 5: input field is ``cron`` — fallback aliases shouldn't
+        override the canonical name."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_C4",
+                    {
+                        "cron": "0 * * * *",
+                        "cron_expression": "* * * * *",  # legacy alias — should be ignored
+                        "prompt": "y",
+                        "recurring": True,
+                    },
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        pending = loop_scheduler.pending_for_chat(7777)
+        assert len(pending) == 1
+        assert pending[0].cron_expression == "0 * * * *"
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_cron_create_skipped_when_prompt_missing(self):
+        """Defensive: missing prompt field → no registration."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_C5",
+                    {"cron": "* * * * *", "recurring": True},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 0
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_schedule_wakeup_registers_when_above_threshold(self):
+        """Long ScheduleWakeup → register Untether-side timer."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        # 3600s > default inline_threshold_seconds=300 — should register.
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "ScheduleWakeup",
+                    "toolu_W1",
+                    {
+                        "delaySeconds": 3600,
+                        "reason": "long-poll",
+                        "prompt": "check progress",
+                    },
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        pending = loop_scheduler.pending_for_chat(7777)
+        assert len(pending) == 1
+        assert pending[0].kind == "wakeup"
+        assert pending[0].delay_seconds == 3600.0
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_schedule_wakeup_skipped_when_below_threshold(self):
+        """Short waits stay rendered live by the rc8 countdown — no
+        Untether-side timer."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "ScheduleWakeup",
+                    "toolu_W2",
+                    {"delaySeconds": 60, "prompt": "x"},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 0
+        # rc8 countdown (live_wakeups) still populated by
+        # _register_background_handle, regardless of loop observation.
+        assert "toolu_W2" in state.live_wakeups
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_cron_delete_cancels_matching_entry(self):
+        """CronDelete with the upstream ID cancels the matching entry."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        # Register an entry, then bind upstream ID, then delete.
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_CD1",
+                    {"cron": "* * * * *", "prompt": "x", "recurring": True},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        # tool_result with upstream ID
+        result = _make_tool_result_event("toolu_CD1")
+        result["message"]["content"][0]["content"] = (
+            "Scheduled recurring job abcdef12 (Every minute). Session-only ..."
+        )
+        translate_claude_event(
+            _decode_event(result),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        # Now CronDelete that ID
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event("CronDelete", "toolu_CD2", {"id": "abcdef12"})
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        assert loop_scheduler.active_count() == 0
+
+    @pytest.mark.usefixtures("_enable_loop", "_set_chat", "_installed_scheduler")
+    async def test_tool_result_binds_upstream_cron_id(self):
+        """``_observe_loop_tool_result`` parses the result text and binds
+        the 8-char upstream ID via :func:`bind_upstream_id`."""
+        from untether import loop_scheduler
+
+        state = ClaudeStreamState()
+        _seed_state_for_loop_observation(state)
+        translate_claude_event(
+            _decode_event(
+                _make_tool_use_event(
+                    "CronCreate",
+                    "toolu_BU1",
+                    {"cron": "* * * * *", "prompt": "x", "recurring": True},
+                )
+            ),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        result = _make_tool_result_event("toolu_BU1")
+        result["message"]["content"][0]["content"] = (
+            "Scheduled recurring job 12345678 (Every minute). Session-only ..."
+        )
+        translate_claude_event(
+            _decode_event(result),
+            title="claude",
+            state=state,
+            factory=state.factory,
+        )
+        # The entry now has upstream_cron_id bound — cancel_by_upstream_id
+        # must succeed.
+        assert loop_scheduler.cancel_by_upstream_id("12345678") is True
+
+    @pytest.mark.usefixtures("_set_chat")
+    async def test_loop_enabled_for_chat_run_options_overrides_global(self):
+        """Per-chat run option True overrides global config False (the
+        common case — user enables Loop mode in their chat)."""
+        from untether.runners.claude import _loop_enabled_for_chat
+        from untether.runners.run_options import (
+            EngineRunOptions,
+            apply_run_options,
+        )
+
+        with apply_run_options(EngineRunOptions(loop_enabled=True)):
+            assert _loop_enabled_for_chat(7777) is True
+        with apply_run_options(EngineRunOptions(loop_enabled=False)):
+            assert _loop_enabled_for_chat(7777) is False
+        # No run options at all → fall back to global ([loop] enabled,
+        # default False).  Use a real options=None context to verify.
+        from untether.runners.run_options import (
+            reset_run_options,
+            set_run_options,
+        )
+
+        token = set_run_options(None)
+        try:
+            assert _loop_enabled_for_chat(7777) is False
+        finally:
+            reset_run_options(token)
+
+
+def test_first_user_message_text_captured_in_new_state() -> None:
+    """new_state should snapshot the prompt for sentinel-fallback later."""
+    runner = ClaudeRunner(
+        claude_cmd="claude",
+        model=None,
+        permission_mode=None,
+        allowed_tools=[],
+        extra_args=[],
+        dangerously_skip_permissions=False,
+        use_api_billing=None,
+        session_title=None,
+    )
+    state = runner.new_state("user typed /loop X", None)
+    assert state.first_user_message_text == "user typed /loop X"
diff --git a/tests/test_claude_schema.py b/tests/test_claude_schema.py
index f3f6c30a..2b8ea7d4 100644
--- a/tests/test_claude_schema.py
+++ b/tests/test_claude_schema.py
@@ -67,3 +67,152 @@ def test_decode_rate_limit_event_bare() -> None:
     decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
     assert isinstance(decoded, claude_schema.StreamRateLimitMessage)
     assert decoded.rate_limit_info is None
+
+
+# ---------------------------------------------------------------------------
+# #489 — server_tool_use + advisor_tool_result content blocks
+# ---------------------------------------------------------------------------
+
+
+def test_decode_server_tool_use_block() -> None:
+    """Anthropic server-side tools (web_search, code_execution, …) emit
+    `server_tool_use` content blocks. Schema must parse them as
+    StreamServerToolUseBlock instead of raising ValidationError."""
+    payload = {
+        "type": "assistant",
+        "uuid": "uuid-1",
+        "session_id": "sess-1",
+        "message": {
+            "role": "assistant",
+            "model": "claude-opus-4-7",
+            "content": [
+                {
+                    "type": "server_tool_use",
+                    "id": "stu_01",
+                    "name": "web_search",
+                    "input": {"query": "untether telegram"},
+                }
+            ],
+        },
+    }
+    decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
+    assert isinstance(decoded, claude_schema.StreamAssistantMessage)
+    assert len(decoded.message.content) == 1
+    block = decoded.message.content[0]
+    assert isinstance(block, claude_schema.StreamServerToolUseBlock)
+    assert block.id == "stu_01"
+    assert block.name == "web_search"
+    assert block.input == {"query": "untether telegram"}
+
+
+def test_decode_advisor_tool_result_block() -> None:
+    """Result of the parent agent's `advisor()` meta-tool. Schema must parse
+    it as StreamAdvisorToolResultBlock instead of raising ValidationError."""
+    payload = {
+        "type": "user",
+        "uuid": "uuid-2",
+        "session_id": "sess-1",
+        "message": {
+            "role": "user",
+            "content": [
+                {
+                    "type": "advisor_tool_result",
+                    "tool_use_id": "adv_01",
+                    "content": "Reviewer said: looks good.",
+                    "is_error": False,
+                }
+            ],
+        },
+    }
+    decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
+    assert isinstance(decoded, claude_schema.StreamUserMessage)
+    assert isinstance(decoded.message.content, list)
+    assert len(decoded.message.content) == 1
+    block = decoded.message.content[0]
+    assert isinstance(block, claude_schema.StreamAdvisorToolResultBlock)
+    assert block.tool_use_id == "adv_01"
+    assert block.content == "Reviewer said: looks good."
+    assert block.is_error is False
+
+
+def test_decode_advisor_tool_result_block_minimal() -> None:
+    """advisor_tool_result with optional fields omitted (content/is_error default)."""
+    payload = {
+        "type": "user",
+        "uuid": "uuid-3",
+        "session_id": "sess-1",
+        "message": {
+            "role": "user",
+            "content": [
+                {"type": "advisor_tool_result", "tool_use_id": "adv_02"},
+            ],
+        },
+    }
+    decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
+    assert isinstance(decoded, claude_schema.StreamUserMessage)
+    assert isinstance(decoded.message.content, list)
+    block = decoded.message.content[0]
+    assert isinstance(block, claude_schema.StreamAdvisorToolResultBlock)
+    assert block.tool_use_id == "adv_02"
+    assert block.content is None
+    assert block.is_error is None
+
+
+# ---------------------------------------------------------------------------
+# #501 — tool_result.content / advisor_tool_result.content as a single dict
+# ---------------------------------------------------------------------------
+
+
+def test_decode_tool_result_block_with_dict_content() -> None:
+    """Claude Code may emit `tool_result.content` as a single content block
+    object (e.g. {"type": "text", "text": "..."}), not just str / list /
+    null. Schema must accept the dict shape so msgspec doesn't drop the
+    line with ValidationError."""
+    payload = {
+        "type": "user",
+        "uuid": "uuid-501a",
+        "session_id": "sess-501",
+        "message": {
+            "role": "user",
+            "content": [
+                {
+                    "type": "tool_result",
+                    "tool_use_id": "tu_501",
+                    "content": {"type": "text", "text": "ok"},
+                    "is_error": False,
+                },
+            ],
+        },
+    }
+    decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
+    assert isinstance(decoded, claude_schema.StreamUserMessage)
+    assert isinstance(decoded.message.content, list)
+    block = decoded.message.content[0]
+    assert isinstance(block, claude_schema.StreamToolResultBlock)
+    assert block.tool_use_id == "tu_501"
+    assert block.content == {"type": "text", "text": "ok"}
+    assert block.is_error is False
+
+
+def test_decode_advisor_tool_result_block_with_dict_content() -> None:
+    """advisor_tool_result with the same dict-content shape as #501."""
+    payload = {
+        "type": "user",
+        "uuid": "uuid-501b",
+        "session_id": "sess-501",
+        "message": {
+            "role": "user",
+            "content": [
+                {
+                    "type": "advisor_tool_result",
+                    "tool_use_id": "adv_501",
+                    "content": {"type": "text", "text": "advice"},
+                },
+            ],
+        },
+    }
+    decoded = claude_schema.decode_stream_json_line(json.dumps(payload).encode())
+    block = decoded.message.content[0]
+    assert isinstance(block, claude_schema.StreamAdvisorToolResultBlock)
+    assert block.tool_use_id == "adv_501"
+    assert block.content == {"type": "text", "text": "advice"}
diff --git a/tests/test_cli_auto_router.py b/tests/test_cli_auto_router.py
index 1b903e61..656c667c 100644
--- a/tests/test_cli_auto_router.py
+++ b/tests/test_cli_auto_router.py
@@ -69,7 +69,13 @@ def _settings() -> UntetherSettings:
     return UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
 
diff --git a/tests/test_cli_chat_id.py b/tests/test_cli_chat_id.py
index ff8e97c6..5266a116 100644
--- a/tests/test_cli_chat_id.py
+++ b/tests/test_cli_chat_id.py
@@ -45,7 +45,13 @@ def test_chat_id_command_uses_config_token(monkeypatch) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "config-token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "config-token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     monkeypatch.setattr(cli, "_load_settings_optional", lambda: (settings, Path("x")))
diff --git a/tests/test_cli_commands.py b/tests/test_cli_commands.py
index 0adff247..b7b1a77c 100644
--- a/tests/test_cli_commands.py
+++ b/tests/test_cli_commands.py
@@ -20,7 +20,9 @@
 def _min_config() -> dict:
     return {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
     }
 
 
@@ -230,7 +232,13 @@ def test_doctor_rejects_non_telegram_transport(monkeypatch) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "local",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     monkeypatch.setattr(cli, "load_settings", lambda: (settings, Path("x")))
diff --git a/tests/test_cli_config.py b/tests/test_cli_config.py
index 4b7bf04a..bd87a873 100644
--- a/tests/test_cli_config.py
+++ b/tests/test_cli_config.py
@@ -12,7 +12,8 @@ def _write_min_config(path: Path) -> None:
         "\n"
         "[transports.telegram]\n"
         'bot_token = "token"\n'
-        "chat_id = 123\n",
+        "chat_id = 123\n"
+        "allow_any_user = true\n",
         encoding="utf-8",
     )
 
@@ -25,7 +26,8 @@ def test_config_list_outputs_flattened(tmp_path: Path) -> None:
         "\n"
         "[transports.telegram]\n"
         'bot_token = "token"\n'
-        "chat_id = 123\n",
+        "chat_id = 123\n"
+        "allow_any_user = true\n",
         encoding="utf-8",
     )
 
@@ -156,6 +158,7 @@ def test_config_unset_prunes_tables(tmp_path: Path) -> None:
         "[transports.telegram]\n"
         'bot_token = "token"\n'
         "chat_id = 123\n"
+        "allow_any_user = true\n"
         "\n"
         "[projects.foo]\n"
         'path = "/tmp/repo"\n',
@@ -181,6 +184,7 @@ def test_config_set_schema_validation_error(tmp_path: Path) -> None:
         "[transports.telegram]\n"
         'bot_token = "token"\n'
         "chat_id = 123\n"
+        "allow_any_user = true\n"
         "\n"
         "[projects.foo]\n"
         'path = "/tmp/repo"\n',
diff --git a/tests/test_cli_doctor.py b/tests/test_cli_doctor.py
index e52265ca..548a1719 100644
--- a/tests/test_cli_doctor.py
+++ b/tests/test_cli_doctor.py
@@ -13,7 +13,13 @@ def _settings() -> UntetherSettings:
     return UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
 
diff --git a/tests/test_cli_helpers.py b/tests/test_cli_helpers.py
index 74bb0eb8..1e26c2be 100644
--- a/tests/test_cli_helpers.py
+++ b/tests/test_cli_helpers.py
@@ -11,7 +11,9 @@
 def _settings(overrides: dict | None = None) -> UntetherSettings:
     payload = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
     }
     if overrides:
         payload.update(overrides)
@@ -107,6 +109,7 @@ def test_doctor_file_checks() -> None:
                 "telegram": {
                     "bot_token": "token",
                     "chat_id": 1,
+                    "allow_any_user": True,
                     "files": {"enabled": True},
                 }
             }
@@ -131,6 +134,7 @@ def test_doctor_voice_checks(monkeypatch) -> None:
                 "telegram": {
                     "bot_token": "token",
                     "chat_id": 1,
+                    "allow_any_user": True,
                     "voice_transcription": True,
                 }
             }
@@ -146,6 +150,7 @@ def test_doctor_voice_checks(monkeypatch) -> None:
                 "telegram": {
                     "bot_token": "token",
                     "chat_id": 1,
+                    "allow_any_user": True,
                     "voice_transcription": True,
                     "voice_transcription_api_key": "local",
                 }
diff --git a/tests/test_command_engine_gates.py b/tests/test_command_engine_gates.py
index 0d8bf352..42dcbcc2 100644
--- a/tests/test_command_engine_gates.py
+++ b/tests/test_command_engine_gates.py
@@ -216,3 +216,53 @@ async def test_planmode_blocked_for_project_engine_codex(self):
         result = await cmd.handle(ctx)  # type: ignore[arg-type]
         assert result is not None
         assert "only available for claude" in result.text.lower()
+
+
+class TestUsageDebugMode:
+    """#410: ``/usage debug`` appends a debug section with cache + token info."""
+
+    @pytest.mark.anyio
+    async def test_debug_section_appended_on_success(self, monkeypatch):
+        from untether.telegram.commands.usage import UsageCommand
+        from untether.utils import usage_cache
+
+        usage_cache.reset_cache()
+
+        async def _fake_fetch(*a, **kw):
+            return {
+                "five_hour": {
+                    "utilization": 12.0,
+                    "resets_at": "2030-01-01T00:00:00+00:00",
+                },
+                "seven_day": {
+                    "utilization": 4.0,
+                    "resets_at": "2030-01-08T00:00:00+00:00",
+                },
+            }
+
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage.fetch_claude_usage", _fake_fetch
+        )
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage._read_token_expiry_ms",
+            lambda: 9_999_999_999_000,  # year 2286 — never expired
+        )
+
+        ctx = FakeCommandContext(
+            runtime=FakeTransportRuntime(default_engine="claude"),
+            args_text="debug",
+        )
+        cmd = UsageCommand()
+        result = await cmd.handle(ctx)  # type: ignore[arg-type]
+        assert result is not None
+        assert "debug" in result.text.lower()
+        assert "OAuth token" in result.text
+        assert "schema mismatches" in result.text
+        # Default /usage (no args) should NOT include the debug block.
+        ctx_plain = FakeCommandContext(
+            runtime=FakeTransportRuntime(default_engine="claude"),
+            args_text="",
+        )
+        result_plain = await cmd.handle(ctx_plain)  # type: ignore[arg-type]
+        assert result_plain is not None
+        assert "🔧 debug" not in result_plain.text
diff --git a/tests/test_config_command.py b/tests/test_config_command.py
index 2fb7d51a..3cc7af9d 100644
--- a/tests/test_config_command.py
+++ b/tests/test_config_command.py
@@ -44,6 +44,13 @@ def _make_ctx(
     ctx.executor = AsyncMock()
     ctx.executor.send = AsyncMock(return_value=None)
     ctx.executor.edit = AsyncMock(return_value=None)
+    # #294: most config tests don't exercise the trigger manager. Default
+    # to None so the home page skips the triggers indicator and the new
+    # `_page_triggers` shows the unavailable branch when invoked.
+    ctx.trigger_manager = None
+    # #271: triggers page reads `ctx.default_chat_id`; default to None so
+    # crons_for_chat / webhooks_for_chat fall back consistently.
+    ctx.default_chat_id = None
     return ctx
 
 
@@ -144,13 +151,13 @@ def test_toast_engine_clear(self):
         assert ConfigCommand.early_answer_toast("ag:clr") == "Engine: cleared"
 
     def test_toast_trigger_all(self):
-        assert ConfigCommand.early_answer_toast("tr:all") == "Trigger: all"
+        assert ConfigCommand.early_answer_toast("tr:all") == "Listen: all"
 
     def test_toast_trigger_mentions(self):
-        assert ConfigCommand.early_answer_toast("tr:men") == "Trigger: mentions"
+        assert ConfigCommand.early_answer_toast("tr:men") == "Listen: mentions"
 
     def test_toast_trigger_clear(self):
-        assert ConfigCommand.early_answer_toast("tr:clr") == "Trigger: cleared"
+        assert ConfigCommand.early_answer_toast("tr:clr") == "Listen: cleared"
 
     def test_toast_navigation_home(self):
         """No toast for navigation to home page."""
@@ -397,6 +404,124 @@ async def test_planmode_guard_unsupported_with_override(self, tmp_path):
 # ---------------------------------------------------------------------------
 
 
+class TestLoopMode:
+    """Cover the new ``/config:loop`` sub-page (#289)."""
+
+    @pytest.mark.anyio
+    async def test_loop_page_renders(self, tmp_path):
+        """Navigating to loop sub-page shows the toggle UI."""
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        ctx = _make_ctx(
+            args_text="loop",
+            text="config:loop",
+            config_path=state_path,
+            default_engine="claude",
+        )
+        await cmd.handle(ctx)
+        msg = _last_edit_msg(ctx)
+        assert "Loop mode" in msg.text
+        # Toggle row + cost-budget deeplink + back
+        assert "config:loop:on" in _buttons_data(msg)
+        assert "config:loop:off" in _buttons_data(msg)
+        assert "config:loop:clr" in _buttons_data(msg)
+        assert "config:cu" in _buttons_data(msg)
+        assert "config:home" in _buttons_data(msg)
+        # Cost+quota warning must be visible before user toggles ON
+        assert "Cost" in msg.text
+        assert "quota" in msg.text.lower()
+
+    @pytest.mark.anyio
+    async def test_loop_page_hidden_for_non_claude(self, tmp_path):
+        """LOOP_SUPPORTED_ENGINES = {claude} — Codex must show the
+        unavailable message instead of the toggle."""
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        ctx = _make_ctx(
+            args_text="loop",
+            text="config:loop",
+            config_path=state_path,
+            default_engine="codex",
+        )
+        await cmd.handle(ctx)
+        msg = _last_edit_msg(ctx)
+        assert "Only available for Claude Code" in msg.text
+        # No toggle buttons in this branch
+        assert "config:loop:on" not in _buttons_data(msg)
+
+    @pytest.mark.anyio
+    async def test_loop_set_on_returns_home(self, tmp_path):
+        """Toggling Loop on returns to home page."""
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        ctx = _make_ctx(
+            args_text="loop:on",
+            text="config:loop:on",
+            config_path=state_path,
+            default_engine="claude",
+        )
+        await cmd.handle(ctx)
+        msg = _last_edit_msg(ctx)
+        assert "settings" in msg.text.lower()  # home page header
+
+    @pytest.mark.anyio
+    async def test_loop_clear_resets_per_chat_override(self, tmp_path):
+        """Clear → loop_enabled goes back to None (follows global)."""
+        from untether.telegram.chat_prefs import (
+            ChatPrefsStore,
+            resolve_prefs_path,
+        )
+
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        # Set on, then clear.
+        ctx = _make_ctx(
+            args_text="loop:on",
+            text="config:loop:on",
+            config_path=state_path,
+            default_engine="claude",
+        )
+        await cmd.handle(ctx)
+        ctx = _make_ctx(
+            args_text="loop:clr",
+            text="config:loop:clr",
+            config_path=state_path,
+            default_engine="claude",
+        )
+        await cmd.handle(ctx)
+        # Verify persisted state is None
+        prefs = ChatPrefsStore(resolve_prefs_path(state_path))
+        override = await prefs.get_engine_override(123, "claude")
+        assert override is None or override.loop_enabled is None
+
+    @pytest.mark.anyio
+    async def test_loop_no_config_path(self):
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="loop", text="config:loop", config_path=None)
+        await cmd.handle(ctx)
+        assert "Unavailable" in _last_edit_msg(ctx).text
+
+    @pytest.mark.anyio
+    async def test_loop_button_in_home_for_claude(self, tmp_path):
+        """The 🔁 Loop mode button must render on the Claude home page."""
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        ctx = _make_ctx(config_path=state_path, default_engine="claude")
+        await cmd.handle(ctx)
+        msg = _last_send_msg(ctx)
+        assert "config:loop" in _buttons_data(msg)
+
+    @pytest.mark.anyio
+    async def test_loop_button_hidden_in_home_for_codex(self, tmp_path):
+        """The 🔁 Loop mode button must NOT render on a Codex home page."""
+        state_path = tmp_path / "prefs.json"
+        cmd = ConfigCommand()
+        ctx = _make_ctx(config_path=state_path, default_engine="codex")
+        await cmd.handle(ctx)
+        msg = _last_send_msg(ctx)
+        assert "config:loop" not in _buttons_data(msg)
+
+
 class TestCodexApprovalPolicy:
     @pytest.mark.anyio
     async def test_approval_policy_page_renders(self, tmp_path):
@@ -846,7 +971,7 @@ async def test_trigger_page_renders(self, tmp_path):
         cmd = ConfigCommand()
         ctx = _make_ctx(args_text="tr", text="config:tr", config_path=state_path)
         await cmd.handle(ctx)
-        assert "Trigger" in _last_edit_msg(ctx).text
+        assert "Listen" in _last_edit_msg(ctx).text
 
     @pytest.mark.anyio
     async def test_trigger_set_mentions_returns_home(self, tmp_path):
@@ -3016,3 +3141,305 @@ def test_toast_bc_off(self):
 
     def test_toast_bc_clr(self):
         assert ConfigCommand.early_answer_toast("cu:bc_clr") == "Auto-cancel: cleared"
+
+
+# ── #294: /config triggers (tg) page ────────────────────────────────────
+
+
+class TestTriggersPage:
+    @pytest.mark.anyio
+    async def test_no_trigger_manager_shows_unavailable(self, tmp_path):
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg")
+        ctx.trigger_manager = None
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "Triggers" in text
+        assert "Unavailable" in text
+
+    @pytest.mark.anyio
+    async def test_no_triggers_configured_shows_empty_message(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg")
+        ctx.trigger_manager = TriggerManager()
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "Triggers" in text
+        assert "No crons or webhooks configured" in text
+
+    @pytest.mark.anyio
+    async def test_pause_action_pauses_manager(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        mgr = TriggerManager(
+            parse_trigger_config(
+                {
+                    "enabled": True,
+                    "crons": [
+                        {"id": "a", "schedule": "0 9 * * *", "prompt": "x"},
+                    ],
+                }
+            )
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg:pause", text="config:tg:pause")
+        ctx.trigger_manager = mgr
+        await cmd.handle(ctx)
+        assert mgr.is_paused is True
+        text = _last_edit_msg(ctx).text
+        # Status reflects the new paused state.
+        assert "paused" in text
+
+    @pytest.mark.anyio
+    async def test_resume_action_resumes_manager(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        mgr = TriggerManager(
+            parse_trigger_config(
+                {
+                    "enabled": True,
+                    "crons": [
+                        {"id": "a", "schedule": "0 9 * * *", "prompt": "x"},
+                    ],
+                }
+            )
+        )
+        mgr.pause()
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg:resume", text="config:tg:resume")
+        ctx.trigger_manager = mgr
+        await cmd.handle(ctx)
+        assert mgr.is_paused is False
+
+    def test_toast_pause_resume(self):
+        assert ConfigCommand.early_answer_toast("tg:pause") == "⏸ Triggers paused"
+        assert ConfigCommand.early_answer_toast("tg:resume") == "▶️ Triggers resumed"
+
+
+# ── #271 Tier 2 + Tier 3: per-chat trigger list + last-fired ──────────────
+
+
+class TestTriggersPagePerChat:
+    @pytest.fixture(autouse=True)
+    def _reset_history(self):
+        from untether.triggers import history
+
+        history.reset_history()
+        yield
+        history.reset_history()
+
+    @pytest.mark.anyio
+    async def test_lists_crons_for_current_chat(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": "morning",
+                        "schedule": "0 9 * * *",
+                        "prompt": "good morning",
+                        "chat_id": 123,
+                        "project": "lba-1",
+                        "engine": "claude",
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "<b>Crons</b>" in text
+        assert "morning" in text
+        # describe_cron output for "0 9 * * *"
+        assert "9:00" in text
+        assert "lba-1" in text
+        assert "claude" in text
+        assert "last <i>never</i>" in text
+
+    @pytest.mark.anyio
+    async def test_lists_webhooks_for_current_chat(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "webhooks": [
+                    {
+                        "id": "gh-push",
+                        "path": "/webhooks/github",
+                        "auth": "hmac-sha256",
+                        "secret": "s" * 32,
+                        "prompt_template": "push from ${repository}",
+                        "chat_id": 123,
+                        "project": "untether",
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "<b>Webhooks</b>" in text
+        assert "gh-push" in text
+        assert "/webhooks/github" in text
+        assert "auth=<i>hmac-sha256</i>" in text
+        assert "untether" in text
+
+    @pytest.mark.anyio
+    async def test_filters_to_current_chat(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": "mine",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                        "chat_id": 123,
+                    },
+                    {
+                        "id": "other-chat",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                        "chat_id": 999,
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "mine" in text
+        assert "other-chat" not in text
+
+    @pytest.mark.anyio
+    async def test_default_chat_id_fallback(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        # Cron has no chat_id; should resolve via default_chat_id.
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": "global",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        ctx.default_chat_id = 123
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        assert "global" in text
+
+    @pytest.mark.anyio
+    async def test_omits_subsection_when_no_chat_triggers(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        # All triggers belong to a different chat.
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": "elsewhere",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                        "chat_id": 999,
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        # Status line still shows total count, but the per-chat lists are absent.
+        assert "1" in text  # cron count in status
+        assert "<b>Crons</b>" not in text
+        assert "<b>Webhooks</b>" not in text
+
+    @pytest.mark.anyio
+    async def test_renders_last_fired_when_history_present(self, tmp_path):
+        from untether.triggers import history
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        history.init_history(tmp_path / "untether.toml")
+        history.record_fired("morning")
+
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": "morning",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                        "chat_id": 123,
+                    },
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        # Should show "just now" since we just recorded.
+        assert "last <i>just now</i>" in text
+
+    @pytest.mark.anyio
+    async def test_cron_list_caps_at_ten_with_overflow_marker(self, tmp_path):
+        from untether.triggers.manager import TriggerManager
+        from untether.triggers.settings import parse_trigger_config
+
+        cfg = parse_trigger_config(
+            {
+                "enabled": True,
+                "crons": [
+                    {
+                        "id": f"c{i:02d}",
+                        "schedule": "0 9 * * *",
+                        "prompt": "x",
+                        "chat_id": 123,
+                    }
+                    for i in range(13)
+                ],
+            }
+        )
+        cmd = ConfigCommand()
+        ctx = _make_ctx(args_text="tg", text="config:tg", chat_id=123)
+        ctx.trigger_manager = TriggerManager(cfg)
+        await cmd.handle(ctx)
+        text = _last_edit_msg(ctx).text
+        # First 10 listed; remaining 3 collapsed into the overflow marker.
+        assert "c00" in text
+        assert "c09" in text
+        assert "c10" not in text
+        assert "…and 3 more" in text
diff --git a/tests/test_config_path_env.py b/tests/test_config_path_env.py
index deb4c8bb..1033dd7a 100644
--- a/tests/test_config_path_env.py
+++ b/tests/test_config_path_env.py
@@ -56,7 +56,8 @@ def test_env_var_used_when_no_path_arg(self, tmp_path: Path, monkeypatch) -> Non
             'transport = "telegram"\n\n'
             "[transports.telegram]\n"
             'bot_token = "tok"\n'
-            "chat_id = 1\n",
+            "chat_id = 1\n"
+            "allow_any_user = true\n",
             encoding="utf-8",
         )
         monkeypatch.setenv(ENV_VAR, str(env_config))
@@ -73,7 +74,8 @@ def test_explicit_path_wins_over_env(self, tmp_path: Path, monkeypatch) -> None:
             'transport = "telegram"\n\n'
             "[transports.telegram]\n"
             'bot_token = "tok"\n'
-            "chat_id = 2\n",
+            "chat_id = 2\n"
+            "allow_any_user = true\n",
             encoding="utf-8",
         )
         monkeypatch.setenv(ENV_VAR, str(env_config))
@@ -104,7 +106,8 @@ def test_env_var_loads_config(self, tmp_path: Path, monkeypatch) -> None:
             'transport = "telegram"\n\n'
             "[transports.telegram]\n"
             'bot_token = "devtoken"\n'
-            "chat_id = 999\n",
+            "chat_id = 999\n"
+            "allow_any_user = true\n",
             encoding="utf-8",
         )
         monkeypatch.setenv(ENV_VAR, str(env_config))
diff --git a/tests/test_config_watch.py b/tests/test_config_watch.py
index 591fec88..5a2bea1b 100644
--- a/tests/test_config_watch.py
+++ b/tests/test_config_watch.py
@@ -70,7 +70,13 @@ async def test_watch_config_applies_runtime(
         settings=UntetherSettings.model_validate(
             {
                 "transport": "telegram",
-                "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+                "transports": {
+                    "telegram": {
+                        "bot_token": "token",
+                        "chat_id": 123,
+                        "allow_any_user": True,
+                    }
+                },
             }
         ),
         runtime_spec=new_spec,
diff --git a/tests/test_cost_tracker.py b/tests/test_cost_tracker.py
index 9e724f0a..4490283e 100644
--- a/tests/test_cost_tracker.py
+++ b/tests/test_cost_tracker.py
@@ -96,3 +96,31 @@ class TestFormatCostAlert:
     def test_formats_message(self):
         alert = CostAlert(level="warning", message="test message")
         assert format_cost_alert(alert) == "test message"
+
+
+class TestConcurrentRecord:
+    """#379: read-modify-write under concurrent callers must not lose updates."""
+
+    def setup_method(self):
+        _reset_daily()
+
+    def test_concurrent_record_run_cost_atomic(self):
+        from concurrent.futures import ThreadPoolExecutor
+
+        n_calls = 200
+        unit_cost = 0.01
+
+        with ThreadPoolExecutor(max_workers=16) as pool:
+            futures = [pool.submit(record_run_cost, unit_cost) for _ in range(n_calls)]
+            for future in futures:
+                future.result()
+
+        # If the read-modify-write were unguarded, concurrent threads racing
+        # the (today, total + cost) assignment would lose updates and the
+        # observed total would be < n * unit. The lock makes this impossible.
+        expected = round(n_calls * unit_cost, 2)
+        observed = round(get_daily_cost(), 2)
+        assert observed == expected, (
+            f"lost cost updates under concurrency: "
+            f"expected ${expected:.2f}, got ${observed:.2f}"
+        )
diff --git a/tests/test_env_audit.py b/tests/test_env_audit.py
index 56c10179..4aafa01d 100644
--- a/tests/test_env_audit.py
+++ b/tests/test_env_audit.py
@@ -66,13 +66,14 @@ def test_returns_only_disallowed_names(self, monkeypatch):
             "PATH": "/usr/bin",
             "HOME": "/home/u",
             "ANTHROPIC_API_KEY": "sk-ant-",
-            "BWS_ACCESS_TOKEN": "0.f3a-...",
+            "BWS_ACCESS_TOKEN": "0.f3a-...",  # #409: now in default allowlist
             "STRIPE_SECRET_KEY": "sk-live-...",
+            "DROP_ME": "leak",
         }
         monkeypatch.setattr(env_audit, "read_proc_environ", lambda pid: fake_env)
 
         result = audit_proc_env(12345)
-        assert result == ["BWS_ACCESS_TOKEN", "STRIPE_SECRET_KEY"]
+        assert result == ["DROP_ME", "STRIPE_SECRET_KEY"]
 
     def test_empty_when_all_allowed(self, monkeypatch):
         fake_env = {"PATH": "/usr/bin", "HOME": "/home/u"}
@@ -82,15 +83,40 @@ def test_empty_when_all_allowed(self, monkeypatch):
     def test_respects_expected_extras(self, monkeypatch):
         fake_env = {
             "PATH": "/usr/bin",
-            "BWS_ACCESS_TOKEN": "x",
+            "STRIPE_SECRET_KEY": "x",
             "CUSTOM_RUNNER_ENV": "y",
         }
         monkeypatch.setattr(env_audit, "read_proc_environ", lambda pid: fake_env)
 
         # CUSTOM_RUNNER_ENV is permitted by the caller as an extra; only
-        # BWS_ACCESS_TOKEN should be reported.
+        # STRIPE_SECRET_KEY should be reported.
         result = audit_proc_env(12345, expected_extras=("CUSTOM_RUNNER_ENV",))
-        assert result == ["BWS_ACCESS_TOKEN"]
+        assert result == ["STRIPE_SECRET_KEY"]
+
+    def test_respects_user_extra_exact(self, monkeypatch):
+        """#409: user-allowed exact names must not be flagged as leaks."""
+        fake_env = {
+            "PATH": "/usr/bin",
+            "OP_SERVICE_ACCOUNT_TOKEN": "1p-...",
+            "STRIPE_SECRET_KEY": "leak",
+        }
+        monkeypatch.setattr(env_audit, "read_proc_environ", lambda pid: fake_env)
+
+        result = audit_proc_env(12345, user_extra_exact=("OP_SERVICE_ACCOUNT_TOKEN",))
+        assert result == ["STRIPE_SECRET_KEY"]
+
+    def test_respects_user_extra_prefix(self, monkeypatch):
+        """#409: user-allowed prefix names must not be flagged as leaks."""
+        fake_env = {
+            "PATH": "/usr/bin",
+            "VAULT_TOKEN": "v",
+            "VAULT_ADDR": "https://vault",
+            "STRIPE_SECRET_KEY": "leak",
+        }
+        monkeypatch.setattr(env_audit, "read_proc_environ", lambda pid: fake_env)
+
+        result = audit_proc_env(12345, user_extra_prefix=("VAULT_",))
+        assert result == ["STRIPE_SECRET_KEY"]
 
     def test_unreadable_returns_empty(self, monkeypatch):
         monkeypatch.setattr(env_audit, "read_proc_environ", lambda pid: None)
diff --git a/tests/test_env_policy.py b/tests/test_env_policy.py
index 315570c8..f2015285 100644
--- a/tests/test_env_policy.py
+++ b/tests/test_env_policy.py
@@ -1,8 +1,15 @@
-"""Tests for `utils/env_policy.py` — the engine-subprocess env allowlist (#198)."""
+"""Tests for `utils/env_policy.py` — the engine-subprocess env allowlist (#198, #409)."""
 
 from __future__ import annotations
 
-from untether.utils.env_policy import _is_allowed, filtered_env, is_allowed
+from untether.utils.env_policy import (
+    _is_allowed,
+    _reset_log_latch_for_tests,
+    filtered_env,
+    is_allowed,
+    is_allowed_with_extras,
+    log_user_extensions_once,
+)
 
 
 class TestIsAllowed:
@@ -12,13 +19,13 @@ def test_exact_allow_returns_true(self):
         assert is_allowed("PATH") is True
         assert is_allowed("ANTHROPIC_API_KEY") is True
         assert is_allowed("UNTETHER_SESSION") is True
+        assert is_allowed("BWS_ACCESS_TOKEN") is True
 
     def test_prefix_allow_returns_true(self):
         assert is_allowed("CLAUDE_CODE_FOO") is True
         assert is_allowed("MCP_SERVER_BAR") is True
 
     def test_disallowed_returns_false(self):
-        assert is_allowed("BWS_ACCESS_TOKEN") is False
         assert is_allowed("AWS_SECRET_ACCESS_KEY") is False
         assert is_allowed("STRIPE_SECRET_KEY") is False
 
@@ -149,3 +156,107 @@ def test_default_source_is_os_environ(self, monkeypatch):
         out = filtered_env()
         assert out.get("ANTHROPIC_API_KEY") == "probe-value"
         assert "DEFINITELY_NOT_ALLOWED_XYZ" not in out
+
+
+class TestUserExtensions:
+    """#409: per-deployment user extras via [security] env_extra_allow /
+    env_extra_prefix_allow surface here as `extra_allow` / `extra_prefix`
+    parameters to filtered_env."""
+
+    def test_is_allowed_with_extras_falls_back_to_default(self):
+        # No extras: behaves identically to is_allowed().
+        assert is_allowed_with_extras("PATH") is True
+        assert is_allowed_with_extras("AWS_SECRET_ACCESS_KEY") is False
+
+    def test_is_allowed_with_extras_admits_user_exact(self):
+        assert (
+            is_allowed_with_extras(
+                "OP_SERVICE_ACCOUNT_TOKEN",
+                extra_exact=["OP_SERVICE_ACCOUNT_TOKEN"],
+            )
+            is True
+        )
+        # Names not in the user exacts still get rejected.
+        assert (
+            is_allowed_with_extras(
+                "OTHER_TOKEN", extra_exact=["OP_SERVICE_ACCOUNT_TOKEN"]
+            )
+            is False
+        )
+
+    def test_is_allowed_with_extras_admits_user_prefix(self):
+        assert is_allowed_with_extras("VAULT_TOKEN", extra_prefix=["VAULT_"]) is True
+        assert is_allowed_with_extras("VAULT_ADDR", extra_prefix=["VAULT_"]) is True
+        assert (
+            is_allowed_with_extras("STRIPE_VAULT_KEY", extra_prefix=["VAULT_"]) is False
+        )
+
+    def test_filtered_env_admits_extra_prefix(self):
+        src = {
+            "VAULT_TOKEN": "v-tok",
+            "VAULT_ADDR": "https://vault",
+            "STRIPE_SECRET_KEY": "sk_live_x",
+            "PATH": "/usr/bin",
+        }
+        out = filtered_env(src, extra_prefix=["VAULT_"])
+        assert out == {
+            "VAULT_TOKEN": "v-tok",
+            "VAULT_ADDR": "https://vault",
+            "PATH": "/usr/bin",
+        }
+
+    def test_filtered_env_combines_extra_allow_and_extra_prefix(self):
+        src = {
+            "DOPPLER_TOKEN": "d-tok",
+            "VAULT_TOKEN": "v-tok",
+            "STRIPE_SECRET_KEY": "leak",
+        }
+        out = filtered_env(
+            src,
+            extra_allow=["DOPPLER_TOKEN"],
+            extra_prefix=["VAULT_"],
+        )
+        assert out == {"DOPPLER_TOKEN": "d-tok", "VAULT_TOKEN": "v-tok"}
+
+    def test_default_still_blocks_random_env_vars(self):
+        """Without user extras, prior denial behaviour is preserved."""
+        src = {"AWS_SECRET_ACCESS_KEY": "leak", "STRIPE_SECRET_KEY": "leak"}
+        assert filtered_env(src) == {}
+
+
+class TestUserExtensionLogging:
+    """#409: log_user_extensions_once emits one structured INFO per process."""
+
+    def setup_method(self):
+        _reset_log_latch_for_tests()
+
+    def teardown_method(self):
+        _reset_log_latch_for_tests()
+
+    def test_logs_once_when_extras_provided(self):
+        from structlog.testing import capture_logs
+
+        with capture_logs() as logs:
+            log_user_extensions_once(
+                extra_exact=["OP_SERVICE_ACCOUNT_TOKEN"],
+                extra_prefix=["VAULT_"],
+            )
+            log_user_extensions_once(
+                extra_exact=["OP_SERVICE_ACCOUNT_TOKEN"],
+                extra_prefix=["VAULT_"],
+            )
+
+        ext_events = [r for r in logs if r.get("event") == "env_policy.user_extension"]
+        assert len(ext_events) == 1
+        assert ext_events[0]["extra_exact"] == ["OP_SERVICE_ACCOUNT_TOKEN"]
+        assert ext_events[0]["extra_prefix"] == ["VAULT_"]
+
+    def test_no_log_when_no_extras(self):
+        from structlog.testing import capture_logs
+
+        with capture_logs() as logs:
+            log_user_extensions_once()
+            log_user_extensions_once(extra_exact=[], extra_prefix=[])
+
+        ext_events = [r for r in logs if r.get("event") == "env_policy.user_extension"]
+        assert ext_events == []
diff --git a/tests/test_exec_bridge.py b/tests/test_exec_bridge.py
index 7d91432b..74898052 100644
--- a/tests/test_exec_bridge.py
+++ b/tests/test_exec_bridge.py
@@ -483,7 +483,7 @@ def set_approval_buttons(self) -> None:
     def set_no_approval(self) -> None:
         self.keyboard = [[{"text": "Cancel"}]]
 
-    def render_progress(self, state, *, elapsed_s, label="working"):
+    def render_progress(self, state, *, elapsed_s, label="working", now=None):
         return RenderedMessage(
             text=f"{label} {elapsed_s:.0f}s",
             extra={"reply_markup": {"inline_keyboard": self.keyboard}},
@@ -500,7 +500,10 @@ def _make_edits(
 ) -> ProgressEdits:
     if clock is None:
         clock = _FakeClock()
-    tracker = ProgressTracker(engine="codex")
+    # #481: thread the FakeClock into the tracker so ActionState
+    # timestamps align with the bridge's clock (otherwise long-running
+    # action age computations would mix wall-clock and fake clock).
+    tracker = ProgressTracker(engine="codex", clock=clock)
     progress_ref = MessageRef(channel_id=123, message_id=1)
     return ProgressEdits(
         transport=transport,
@@ -818,12 +821,15 @@ def _reset_usage_cache(self):
         from untether.utils import usage_cache
 
         usage_cache.reset_cache()
-        # Also reset the schema-warning latch so tests can exercise it more than once.
+        # Reset the schema-mismatch counter (#410: per-call counter
+        # replaces the old one-shot latch).
         import untether.runner_bridge as rb
 
+        rb._USAGE_SCHEMA_MISMATCH_COUNT = 0
         rb._USAGE_SCHEMA_WARNED = False
         yield
         usage_cache.reset_cache()
+        rb._USAGE_SCHEMA_MISMATCH_COUNT = 0
         rb._USAGE_SCHEMA_WARNED = False
 
     @pytest.mark.anyio
@@ -853,8 +859,9 @@ async def _fake_fetch():
         assert "\u26a1" in result.text
 
     @pytest.mark.anyio
-    async def test_schema_mismatch_warning_fires_once(self, monkeypatch):
-        """Missing expected fields in the usage payload log a one-shot warning."""
+    async def test_schema_mismatch_warning_fires_every_call(self, monkeypatch):
+        """#410: schema_mismatch promotes from one-shot to per-call counter so
+        the issue-watcher fires for ongoing drift, not just the first hit."""
         from untether import runner_bridge as rb
 
         async def _fake_fetch():
@@ -875,13 +882,27 @@ def _warn(event: str, **kwargs) -> None:
 
         monkeypatch.setattr(rb.logger, "warning", _warn)
 
-        msg = RenderedMessage(text="Done.", extra={})
-        await rb._maybe_append_usage_footer(msg, always_show=True)
-        await rb._maybe_append_usage_footer(msg, always_show=True)
+        # Call _validate_usage_schema directly to exercise per-call behaviour
+        # (the cached fetcher path memoises within the TTL window).
+        rb._validate_usage_schema(
+            {"five_hour": {"utilization": 25.0}, "seven_day": {"utilization": 10.0}}
+        )
+        rb._validate_usage_schema(
+            {"five_hour": {"utilization": 25.0}, "seven_day": {"utilization": 10.0}}
+        )
+        rb._validate_usage_schema(
+            {"five_hour": {"utilization": 25.0}, "seven_day": {"utilization": 10.0}}
+        )
 
         mismatch = [c for c in warn_calls if c[0] == "claude_usage.schema_mismatch"]
-        assert len(mismatch) == 1  # fires exactly once
+        assert len(mismatch) == 3  # one per call now, not one per process
         assert mismatch[0][1]["missing"]  # has a non-empty list
+        # #410: structured log carries a cumulative count field.
+        assert mismatch[0][1]["count"] == 1
+        assert mismatch[1][1]["count"] == 2
+        assert mismatch[2][1]["count"] == 3
+        # Public accessor reports the same count.
+        assert rb.get_usage_schema_mismatch_count() == 3
 
     @pytest.mark.anyio
     async def test_always_show_false_hides_below_threshold(self, monkeypatch):
@@ -5078,3 +5099,503 @@ async def test_on_event_clears_stuck_state(self) -> None:
         )
         await edits.on_event(evt)
         assert edits._stuck_state is None
+
+
+# ---------------------------------------------------------------------------
+# #470 + #481: expected-wait suppression matrix + post-result closing message.
+# ---------------------------------------------------------------------------
+
+
+def _make_engine_state(**fields):
+    """Build a SimpleNamespace mocking ClaudeStreamState for stall tests.
+
+    The bridge's expected-wait helpers (``_is_post_result_idle``,
+    ``_has_pending_wakeup``, ``_has_active_monitor``) duck-type against
+    ``stream.engine_state`` so a SimpleNamespace with the right attrs is
+    sufficient.
+    """
+    from types import SimpleNamespace
+
+    defaults: dict = {
+        "result_received_at": None,
+        "live_wakeups": {},
+        "live_monitors": {},
+        "live_bg_bashes": set(),
+        "live_bg_agents": set(),
+        "live_remote_triggers": set(),
+        "post_result_closed_at": None,
+        "post_result_idle_minutes": 0.0,
+        "post_result_closing_sent": False,
+    }
+    defaults.update(fields)
+    return SimpleNamespace(**defaults)
+
+
+def _make_stream(*, last_event_type="user", engine_state=None):
+    """Mock JsonlStreamState for stall tests."""
+    from collections import deque
+    from types import SimpleNamespace
+
+    return SimpleNamespace(
+        recent_events=deque([(1.0, "system"), (2.0, "assistant")], maxlen=10),
+        last_event_type=last_event_type,
+        stderr_capture=[],
+        engine_state=engine_state,
+    )
+
+
+@pytest.mark.anyio
+async def test_stall_post_result_suppressed_when_result_armed() -> None:
+    """#470: stream.last_event_type == 'result' suppresses Telegram notification."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+
+    edits.stream = _make_stream(
+        last_event_type="result",
+        engine_state=_make_engine_state(result_received_at=99.0),
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    # No Telegram stall warning sent (post-result suppression).
+    stall_msgs = [c for c in transport.send_calls if "min" in c["message"].text]
+    assert stall_msgs == []
+
+
+@pytest.mark.anyio
+async def test_stall_post_result_blocks_auto_cancel() -> None:
+    """#470: post-result idle blocks the max_warnings auto-cancel arm."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+    edits._STALL_MAX_WARNINGS = 2  # easy to cross
+    cancel_event = anyio.Event()
+    edits.cancel_event = cancel_event
+
+    edits.stream = _make_stream(
+        last_event_type="result",
+        engine_state=_make_engine_state(result_received_at=99.0),
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.2)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    assert not cancel_event.is_set()
+
+
+@pytest.mark.anyio
+async def test_stall_post_result_overridden_by_frozen_ring() -> None:
+    """#470: genuinely-frozen post-result session still warns (frozen-ring wins)."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+    # Pre-arm frozen-ring count AND prev_recent_events so the first stall
+    # tick increments (instead of resetting to 0) and frozen_escalate
+    # fires immediately. The deque content is set by _make_stream() —
+    # match the rounded snapshot the bridge will compute.
+    edits._frozen_ring_count = 4  # 4 + 1 (this tick) = 5, past threshold
+    edits._prev_recent_events = [(1.0, "system"), (2.0, "assistant")]
+
+    edits.stream = _make_stream(
+        last_event_type="result",
+        engine_state=_make_engine_state(result_received_at=99.0),
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    # Frozen-ring escalation overrides post-result suppression.
+    stall_msgs = [c for c in transport.send_calls if "No progress" in c["message"].text]
+    assert len(stall_msgs) >= 1
+
+
+@pytest.mark.anyio
+async def test_stall_schedule_wakeup_suppressed_when_deadline_future() -> None:
+    """#481: ScheduleWakeup with future deadline suppresses warning."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+
+    # Deadline 1000s in the future (well beyond the test clock advance).
+    import time as _t
+
+    edits.stream = _make_stream(
+        engine_state=_make_engine_state(
+            live_wakeups={"toolu_1": _t.monotonic() + 1000.0}
+        )
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    stall_msgs = [c for c in transport.send_calls if "min" in c["message"].text]
+    assert stall_msgs == []
+
+
+@pytest.mark.anyio
+async def test_stall_schedule_wakeup_overridden_by_frozen_ring() -> None:
+    """#481: genuinely-frozen ScheduleWakeup session still warns."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+    edits._frozen_ring_count = 4
+    edits._prev_recent_events = [(1.0, "system"), (2.0, "assistant")]
+
+    import time as _t
+
+    edits.stream = _make_stream(
+        engine_state=_make_engine_state(
+            live_wakeups={"toolu_1": _t.monotonic() + 1000.0}
+        )
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    stall_msgs = [c for c in transport.send_calls if "No progress" in c["message"].text]
+    assert len(stall_msgs) >= 1
+
+
+@pytest.mark.anyio
+async def test_stall_bash_grace_suppressed_within_window() -> None:
+    """#481: recent Bash within bash_grace_seconds suppresses warning."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+    # Long grace window — covers the entire test.
+    edits._bash_grace_seconds = 10.0
+
+    edits.stream = _make_stream()
+
+    from untether.model import Action, ActionEvent
+
+    evt = ActionEvent(
+        engine="claude",
+        action=Action(
+            id="a1",
+            kind="command",
+            title="ls -la",
+            detail={"name": "Bash", "input": {"command": "ls -la"}},
+        ),
+        phase="started",
+    )
+    await edits.on_event(evt)
+    clock.set(101.0)  # 1s after action start — well within 10s grace
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(101.5)  # past stall threshold but within bash grace
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    stall_msgs = [c for c in transport.send_calls if "min" in c["message"].text]
+    assert stall_msgs == []
+
+
+@pytest.mark.anyio
+async def test_stall_bash_fresh_output_suppressed() -> None:
+    """#481: BashOutput within stall_threshold/2 suppresses warning."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 10.0  # threshold/2 = 5.0
+    edits._STALL_THRESHOLD_TOOL = 10.0
+    edits._STALL_THRESHOLD_APPROVAL = 100.0
+    edits._stall_repeat_seconds = 1000.0
+    edits._bash_grace_seconds = 0.1  # disable grace; only fresh-output gates
+
+    edits.stream = _make_stream()
+
+    from untether.model import Action, ActionEvent
+
+    # Drive clock to 110, then fire BashOutput so its last_update_at = 110.
+    # At stall check (clock=113), 113-110=3 s is within the 5 s freshness
+    # window; 113-100=13 s is past the 10 s stall threshold.
+    clock.set(110.0)
+    evt = ActionEvent(
+        engine="claude",
+        action=Action(
+            id="a1",
+            kind="tool",
+            title="BashOutput",
+            detail={"name": "BashOutput", "input": {"bash_id": "shell_x"}},
+        ),
+        phase="completed",
+        ok=True,
+    )
+    await edits.on_event(evt)
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(113.0)
+            await anyio.sleep(0.05)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    stall_msgs = [c for c in transport.send_calls if "min" in c["message"].text]
+    assert stall_msgs == []
+
+
+@pytest.mark.anyio
+async def test_stall_monitor_active_suppressed() -> None:
+    """#481: active Monitor with future deadline suppresses warning."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 0.05
+    edits._STALL_THRESHOLD_TOOL = 0.05
+    edits._STALL_THRESHOLD_APPROVAL = 10.0
+    # Long repeat seconds so only 1 stall tick fires within the test window —
+    # otherwise the unchanging fake recent_events deque escalates frozen-ring
+    # past the 3-tick threshold and overrides these suppressions (which is
+    # the spec — see test_stall_post_result_overridden_by_frozen_ring).
+    edits._stall_repeat_seconds = 1000.0
+
+    import time as _t
+
+    edits.stream = _make_stream(
+        engine_state=_make_engine_state(
+            live_monitors={"toolu_m1": _t.monotonic() + 1000.0}
+        )
+    )
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            clock.set(110.0)
+            await anyio.sleep(0.15)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    stall_msgs = [c for c in transport.send_calls if "min" in c["message"].text]
+    assert stall_msgs == []
+
+
+@pytest.mark.anyio
+async def test_post_result_closing_message_sent() -> None:
+    """#470: closing message fires when post_result_closed_at is stamped."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 100.0  # never stall during test
+    edits._STALL_THRESHOLD_TOOL = 100.0
+    edits._STALL_THRESHOLD_APPROVAL = 100.0
+
+    import time as _t
+
+    es = _make_engine_state(
+        post_result_closed_at=_t.monotonic(),
+        post_result_idle_minutes=10.0,
+        post_result_closing_sent=False,
+    )
+    edits.stream = _make_stream(engine_state=es)
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            await anyio.sleep(0.05)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    closing = [
+        c
+        for c in transport.send_calls
+        if "turn complete" in c["message"].text and "10m idle" in c["message"].text
+    ]
+    assert len(closing) == 1
+    assert es.post_result_closing_sent is True
+
+
+@pytest.mark.anyio
+async def test_post_result_closing_message_idempotent() -> None:
+    """#470: closing message fires exactly once even with multiple ticks."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 0.01
+    edits._STALL_THRESHOLD_SECONDS = 100.0
+    edits._STALL_THRESHOLD_TOOL = 100.0
+    edits._STALL_THRESHOLD_APPROVAL = 100.0
+
+    import time as _t
+
+    es = _make_engine_state(
+        post_result_closed_at=_t.monotonic(),
+        post_result_idle_minutes=12.0,
+        post_result_closing_sent=False,
+    )
+    edits.stream = _make_stream(engine_state=es)
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            await anyio.sleep(0.2)  # many ticks at 0.01s
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    closing = [c for c in transport.send_calls if "turn complete" in c["message"].text]
+    assert len(closing) == 1
+
+
+@pytest.mark.anyio
+async def test_heartbeat_mutates_schedule_wakeup_countdown() -> None:
+    """#481: heartbeat tick injects detail['countdown_s'] for ScheduleWakeup."""
+    transport = FakeTransport()
+    presenter = _KeyboardPresenter()
+    clock = _FakeClock(start=100.0)
+    edits = _make_edits(transport, presenter, clock=clock)
+    edits._stall_check_interval = 100.0  # disable stall path
+    edits._heartbeat_interval = 0.01
+
+    import time as _t
+
+    deadline = _t.monotonic() + 60.0
+    es = _make_engine_state(live_wakeups={"toolu_w1": deadline})
+    edits.stream = _make_stream(engine_state=es)
+
+    from untether.model import Action, ActionEvent
+
+    evt = ActionEvent(
+        engine="claude",
+        action=Action(
+            id="toolu_w1",
+            kind="tool",
+            title="ScheduleWakeup",
+            detail={
+                "name": "ScheduleWakeup",
+                "input": {"delaySeconds": 60, "reason": "build check"},
+            },
+        ),
+        phase="started",
+    )
+    await edits.on_event(evt)
+
+    async with anyio.create_task_group() as tg:
+
+        async def drive() -> None:
+            await anyio.sleep(0.05)
+            edits.signal_send.close()
+
+        tg.start_soon(edits.run)
+        tg.start_soon(drive)
+
+    action_state = next(iter(edits.tracker._actions.values()))
+    assert "countdown_s" in action_state.action.detail
+    assert action_state.action.detail["countdown_s"] >= 0
diff --git a/tests/test_exec_runner.py b/tests/test_exec_runner.py
index efc054a5..1b9999e3 100644
--- a/tests/test_exec_runner.py
+++ b/tests/test_exec_runner.py
@@ -688,3 +688,63 @@ def test_resume_line_proxy_current_stream_no_attr() -> None:
     runner = MockRunner(engine="mock")
     proxy = _ResumeLineProxy(runner=runner)
     assert proxy.current_stream is None
+
+
+# ===========================================================================
+# #505 — base runner _iter_jsonl_events breaks after CompletedEvent
+# ===========================================================================
+
+
+@pytest.mark.anyio
+async def test_base_iter_jsonl_breaks_on_did_emit_completed() -> None:
+    """Base ``_iter_jsonl_events`` must stop reading stdout after a
+    CompletedEvent. Without the break, a child process inheriting the
+    stdout fd (e.g. MCP server, backgrounded shell) would keep the pipe
+    open and the loop would block on ``iter_json_lines`` waiting for an
+    EOF that never comes.
+
+    Validates the fix for #505 by replacing ``iter_json_lines`` with a
+    stub that yields a ``TurnCompleted`` line then a ``hang`` event that
+    never fires. Without the break, the test would deadlock.
+    """
+    import anyio
+    import structlog
+
+    from untether.runner import JsonlStreamState
+
+    runner = CodexRunner(codex_cmd="codex", extra_args=[])
+    state = runner.new_state("hi", ResumeToken(engine=CODEX_ENGINE, value="sid"))
+
+    completed_line = (
+        b'{"type":"turn.completed","turn_id":"t1","usage":{"input_tokens":1,'
+        b'"cached_input_tokens":0,"output_tokens":1,"reasoning_output_tokens":0,'
+        b'"total_tokens":2}}'
+    )
+
+    async def fake_iter_json_lines(_stream):
+        yield completed_line
+        # Without the break, the runner would await this event forever and the
+        # test would hang past the fail_after deadline.
+        await anyio.Event().wait()
+        yield b"never reached"
+
+    runner.iter_json_lines = fake_iter_json_lines  # type: ignore[assignment]
+
+    stream = JsonlStreamState(expected_session=None)
+    logger = structlog.get_logger()
+
+    with anyio.fail_after(2.0):
+        events: list[UntetherEvent] = [
+            evt
+            async for evt in runner._iter_jsonl_events(
+                stdout=None,
+                stream=stream,
+                state=state,
+                resume=None,
+                logger=logger,
+                pid=1234,
+            )
+        ]
+
+    assert stream.did_emit_completed is True
+    assert any(isinstance(e, CompletedEvent) for e in events)
diff --git a/tests/test_logging_redaction.py b/tests/test_logging_redaction.py
new file mode 100644
index 00000000..78fd29fd
--- /dev/null
+++ b/tests/test_logging_redaction.py
@@ -0,0 +1,83 @@
+"""Token redaction processor coverage (#213, prior bot-token work).
+
+The structlog `_redact_event_dict` processor must strip:
+- Telegram bot tokens (`123456789:ABCdef...` and `bot123:...`)
+- OpenAI API keys (`sk-...`)
+- OpenAI project keys (`sk-proj-...`) — distinct char set from generic sk- (#213)
+- GitHub tokens (`ghp_`, `ghs_`, `gho_`, `github_pat_`)
+"""
+
+from __future__ import annotations
+
+from untether.logging import _redact_event_dict, _redact_text
+
+
+class TestRedactText:
+    def test_redacts_telegram_bot_token(self) -> None:
+        out = _redact_text("token=123456789:ABCdefGHIjklMNOpqrsTUVwxyz")
+        assert "ABCdef" not in out
+        assert "[REDACTED_TOKEN]" in out
+
+    def test_redacts_telegram_with_bot_prefix(self) -> None:
+        out = _redact_text(
+            "https://api.telegram.org/bot123456789:abcXYZ_token-value/getMe"
+        )
+        assert "abcXYZ_token" not in out
+        assert "bot[REDACTED]" in out
+
+    def test_redacts_openai_classic_key(self) -> None:
+        out = _redact_text("OPENAI_API_KEY=sk-abcdefghij1234567890ABCDEF")
+        assert "sk-abcdefghij" not in out
+        assert "[REDACTED_KEY]" in out
+
+    def test_redacts_openai_project_key(self) -> None:
+        # #213: sk-proj- variant uses underscore/hyphen, missed by the
+        # generic [A-Za-z0-9] sk- pattern.
+        out = _redact_text("key=sk-proj-AbC_dEf-GhI_jKl-MnO_pQr-StU_vWx-YzAbCdEfGh")
+        assert "sk-proj-AbC_dEf" not in out
+        assert "[REDACTED_KEY]" in out
+
+    def test_redacts_github_pat(self) -> None:
+        out = _redact_text("token github_pat_11ABCDE0_supersecretvalue123")
+        assert "supersecret" not in out
+        assert "[REDACTED_TOKEN]" in out
+
+    def test_preserves_unmatched_text(self) -> None:
+        text = "Just a normal log line without any secrets at all."
+        assert _redact_text(text) == text
+
+
+class TestRedactEventDict:
+    def test_redacts_string_values(self) -> None:
+        out = _redact_event_dict(
+            None, "info", {"event": "ok", "key": "sk-abc1234567890ABCDEFGH"}
+        )
+        assert "sk-abc" not in out["key"]
+        assert "[REDACTED_KEY]" in out["key"]
+
+    def test_redacts_nested_dict(self) -> None:
+        ed = {
+            "event": "error",
+            "details": {"api_key": "sk-proj-aaa_bbb-ccc_ddd-eee_fff-ggg_hhh"},
+        }
+        out = _redact_event_dict(None, "info", ed)
+        assert "sk-proj-aaa" not in out["details"]["api_key"]
+        assert "[REDACTED_KEY]" in out["details"]["api_key"]
+
+    def test_redacts_list_items(self) -> None:
+        ed = {
+            "event": "headers",
+            "items": ["X-Foo: bar", "Authorization: sk-abc1234567890ABCDEFGH"],
+        }
+        out = _redact_event_dict(None, "info", ed)
+        assert all("sk-abc" not in item for item in out["items"])
+
+    def test_redacts_bytes_value(self) -> None:
+        ed = {"event": "raw", "blob": b"telegram_token=987654321:UnSafe_value-xyz"}
+        out = _redact_event_dict(None, "info", ed)
+        assert (
+            b"UnSafe_value" not in out["blob"].encode()
+            if isinstance(out["blob"], str)
+            else True
+        )
+        assert "[REDACTED_TOKEN]" in out["blob"]
diff --git a/tests/test_loop_scheduler.py b/tests/test_loop_scheduler.py
new file mode 100644
index 00000000..acac9d87
--- /dev/null
+++ b/tests/test_loop_scheduler.py
@@ -0,0 +1,770 @@
+"""Tests for the loop_scheduler module (#289).
+
+Covers registration, persistence, cancellation, the fire path, the
+do-not-resume sentinel, and restart resilience.  Mirrors the shape of
+``test_at_command.py``: ``FakeTransport`` + ``RunJobRecorder`` + an
+optional ``runtime`` stand-in for tests that exercise the chat→engine
+freeze.
+"""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+from pathlib import Path
+from typing import Any
+
+import anyio
+import pytest
+
+from untether import loop_scheduler
+from untether.context import RunContext
+from untether.transport import MessageRef
+
+pytestmark = pytest.mark.anyio
+
+
+# ── Fakes ────────────────────────────────────────────────────────────────
+
+
+@dataclass
+class FakeTransport:
+    sent: list[Any] = None  # type: ignore[assignment]
+
+    def __post_init__(self):
+        self.sent = []
+
+    async def send(self, *, channel_id, message, options=None, **_):
+        self.sent.append((channel_id, message.text, options))
+        return MessageRef(channel_id=channel_id, message_id=9999)
+
+    async def edit(self, *, ref, message, **_):
+        return ref
+
+    async def delete(self, ref):
+        return None
+
+
+class RunJobRecorder:
+    def __init__(self) -> None:
+        self.calls: list[tuple] = []
+
+    async def __call__(self, *args, **kwargs):
+        self.calls.append(args)
+
+
+async def _noop_run_job(*args, **kwargs):
+    return None
+
+
+# ── Helpers ──────────────────────────────────────────────────────────────
+
+
+def _register_simple_cron(
+    chat_id: int = 100,
+    *,
+    session_id: str = "sess-abc",
+    tool_use_id: str | None = None,
+    prompt: str = "check deploy",
+    cron_expression: str = "*/5 * * * *",
+    recurring: bool = True,
+) -> str:
+    if tool_use_id is None:
+        tool_use_id = f"tu-{chat_id}-{prompt[:8]}"
+    return loop_scheduler.register_pending_cron(
+        session_id=session_id,
+        tool_use_id=tool_use_id,
+        cron_expression=cron_expression,
+        prompt=prompt,
+        recurring=recurring,
+        chat_id=chat_id,
+    )
+
+
+# ── Install / uninstall lifecycle ───────────────────────────────────────
+
+
+class TestInstallUninstall:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_register_when_not_installed_raises(self):
+        with pytest.raises(loop_scheduler.LoopSchedulerError):
+            loop_scheduler.register_pending_cron(
+                session_id="sess",
+                tool_use_id="tu1",
+                cron_expression="* * * * *",
+                prompt="x",
+                recurring=True,
+                chat_id=1,
+            )
+
+    async def test_install_then_uninstall_clears_state(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                _register_simple_cron(chat_id=42)
+                assert loop_scheduler.active_count() == 1
+            finally:
+                tg.cancel_scope.cancel()
+        loop_scheduler.uninstall()
+        assert loop_scheduler.active_count() == 0
+
+    async def test_uninstall_clears_do_not_resume(self):
+        loop_scheduler.mark_do_not_resume("sess-xyz")
+        assert loop_scheduler.is_do_not_resume("sess-xyz")
+        loop_scheduler.uninstall()
+        assert not loop_scheduler.is_do_not_resume("sess-xyz")
+
+
+# ── Registration ────────────────────────────────────────────────────────
+
+
+class TestRegisterCron:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_register_recurring_cron(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=7, prompt="ping")
+                assert token.startswith("ut_loop_")
+                pending = loop_scheduler.pending_for_chat(7)
+                assert len(pending) == 1
+                assert pending[0].kind == "cron"
+                assert pending[0].cron_expression == "*/5 * * * *"
+                assert pending[0].prompt == "ping"
+                assert pending[0].recurring is True
+                assert pending[0].fire_at_monotonic > 0
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_one_shot_cron(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(
+                    chat_id=8, recurring=False, prompt="reminder"
+                )
+                pending = loop_scheduler.pending_for_chat(8)
+                assert len(pending) == 1
+                assert pending[0].recurring is False
+                assert pending[0].token == token
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_invalid_cron_raises(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                with pytest.raises(loop_scheduler.LoopSchedulerError):
+                    loop_scheduler.register_pending_cron(
+                        session_id="s",
+                        tool_use_id="t",
+                        cron_expression="not-a-cron",
+                        prompt="p",
+                        recurring=True,
+                        chat_id=9,
+                    )
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_stamps_trigger_source_loop(self):
+        """Trigger source ``loop:<token>`` shows in the run footer."""
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=10)
+                entry = loop_scheduler.pending_for_chat(10)[0]
+                assert entry.context is not None
+                assert entry.context.trigger_source == f"loop:{token}"
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_preserves_project_in_context(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                ctx = RunContext(project="acme", branch=None)
+                loop_scheduler.register_pending_cron(
+                    session_id="s",
+                    tool_use_id="t",
+                    cron_expression="* * * * *",
+                    prompt="p",
+                    recurring=True,
+                    chat_id=11,
+                    context=ctx,
+                    engine_override="claude",
+                )
+                entry = loop_scheduler.pending_for_chat(11)[0]
+                assert entry.context.project == "acme"
+                assert entry.engine_override == "claude"
+            finally:
+                tg.cancel_scope.cancel()
+
+
+class TestRegisterWakeup:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_register_wakeup(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                token = loop_scheduler.register_pending_wakeup(
+                    session_id="s",
+                    tool_use_id="t",
+                    delay_seconds=600.0,
+                    prompt="check",
+                    chat_id=20,
+                )
+                pending = loop_scheduler.pending_for_chat(20)
+                assert len(pending) == 1
+                assert pending[0].kind == "wakeup"
+                assert pending[0].delay_seconds == 600.0
+                assert pending[0].recurring is False
+                assert pending[0].token == token
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_wakeup_zero_delay_raises(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                with pytest.raises(loop_scheduler.LoopSchedulerError):
+                    loop_scheduler.register_pending_wakeup(
+                        session_id="s",
+                        tool_use_id="t",
+                        delay_seconds=0,
+                        prompt="x",
+                        chat_id=21,
+                    )
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_register_wakeup_with_fallback(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                loop_scheduler.register_pending_wakeup(
+                    session_id="s",
+                    tool_use_id="t",
+                    delay_seconds=120,
+                    prompt="<<autonomous-loop-dynamic>>",
+                    fallback_first_user_message="poll the build",
+                    chat_id=22,
+                )
+                entry = loop_scheduler.pending_for_chat(22)[0]
+                assert entry.fallback_first_user_message == "poll the build"
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── Upstream-ID binding ─────────────────────────────────────────────────
+
+
+class TestBindUpstreamId:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_bind_then_cancel_by_upstream_id(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                _register_simple_cron(chat_id=30, tool_use_id="tu-bind-1")
+                loop_scheduler.bind_upstream_id("tu-bind-1", "abcdef12")
+                assert loop_scheduler.cancel_by_upstream_id("abcdef12") is True
+                assert loop_scheduler.active_count() == 0
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_bind_unknown_tool_use_id_is_noop(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                # Should not raise.
+                loop_scheduler.bind_upstream_id("nonexistent", "deadbeef")
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_cancel_by_unknown_upstream_id_returns_false(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                assert loop_scheduler.cancel_by_upstream_id("nope") is False
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── Cancellation ────────────────────────────────────────────────────────
+
+
+class TestCancellation:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_cancel_by_token_marks_do_not_resume(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=40, session_id="sess-40")
+                assert loop_scheduler.cancel_by_token(token) is True
+                assert loop_scheduler.is_do_not_resume("sess-40") is True
+                assert loop_scheduler.active_count() == 0
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_cancel_by_unknown_token_returns_false(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                assert loop_scheduler.cancel_by_token("nope") is False
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_cancel_pending_for_chat_only_drops_chat(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                _register_simple_cron(chat_id=50, prompt="a", tool_use_id="tu-50a")
+                _register_simple_cron(chat_id=50, prompt="b", tool_use_id="tu-50b")
+                _register_simple_cron(chat_id=51, prompt="c", tool_use_id="tu-51c")
+                cancelled = loop_scheduler.cancel_pending_for_chat(50)
+                assert cancelled == 2
+                assert loop_scheduler.active_count() == 1
+                assert loop_scheduler.pending_for_chat(51)[0].prompt == "c"
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── Inspection ──────────────────────────────────────────────────────────
+
+
+class TestInspection:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_active_count_excludes_cancelled(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                t1 = _register_simple_cron(chat_id=60, prompt="a", tool_use_id="t60a")
+                _register_simple_cron(chat_id=60, prompt="b", tool_use_id="t60b")
+                assert loop_scheduler.active_count() == 2
+                loop_scheduler.cancel_by_token(t1)
+                assert loop_scheduler.active_count() == 1
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_next_fire_for_session_returns_min(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                loop_scheduler.register_pending_wakeup(
+                    session_id="sess-shared",
+                    tool_use_id="t1",
+                    delay_seconds=600,
+                    prompt="x",
+                    chat_id=70,
+                )
+                loop_scheduler.register_pending_wakeup(
+                    session_id="sess-shared",
+                    tool_use_id="t2",
+                    delay_seconds=120,
+                    prompt="y",
+                    chat_id=70,
+                )
+                next_fire = loop_scheduler.next_fire_for_session("sess-shared")
+                assert next_fire is not None
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_next_fire_for_unknown_session_is_none(self):
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                assert loop_scheduler.next_fire_for_session("nope") is None
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── Cron next-fire computation ──────────────────────────────────────────
+
+
+class TestNextCronFire:
+    def test_simple_every_minute(self):
+        result = loop_scheduler._next_cron_fire("* * * * *")
+        assert result is not None
+        assert result > 0
+
+    def test_malformed_returns_none(self):
+        assert loop_scheduler._next_cron_fire("not-a-cron") is None
+        assert loop_scheduler._next_cron_fire("") is None
+        assert loop_scheduler._next_cron_fire("* * *") is None
+
+    def test_every_5_minutes(self):
+        result = loop_scheduler._next_cron_fire("*/5 * * * *")
+        assert result is not None
+
+
+# ── Fire path ───────────────────────────────────────────────────────────
+
+
+class TestFirePath:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_fire_skips_cancelled_entry(self):
+        recorder = RunJobRecorder()
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=80)
+                loop_scheduler.cancel_by_token(token)
+                # Should be a no-op even though the token still has an entry
+                # in the cancelled state.
+                await loop_scheduler._fire(token)
+                assert recorder.calls == []
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_skips_unknown_token(self):
+        recorder = RunJobRecorder()
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                await loop_scheduler._fire("ut_loop_deadbeef")
+                assert recorder.calls == []
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_skips_when_max_iterations_reached(self):
+        recorder = RunJobRecorder()
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = loop_scheduler.register_pending_cron(
+                    session_id="s",
+                    tool_use_id="t",
+                    cron_expression="* * * * *",
+                    prompt="p",
+                    recurring=True,
+                    chat_id=81,
+                    max_iterations=1,
+                )
+                entry = loop_scheduler._PENDING_BY_TOKEN[token]
+                entry.iteration_count = 1  # already at cap
+                await loop_scheduler._fire(token)
+                assert recorder.calls == []
+                assert entry.cancelled is True
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_skips_when_do_not_resume_set(self):
+        recorder = RunJobRecorder()
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=82, session_id="sess-blocked")
+                loop_scheduler.mark_do_not_resume("sess-blocked")
+                await loop_scheduler._fire(token)
+                assert recorder.calls == []
+                # Entry should be expired (not just skipped).
+                assert token not in loop_scheduler._PENDING_BY_TOKEN
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_drops_when_chat_busy(self):
+        recorder = RunJobRecorder()
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg,
+                recorder,
+                FakeTransport(),
+                1,
+                is_chat_busy=lambda _chat_id: True,
+            )
+            try:
+                token = _register_simple_cron(chat_id=83)
+                await loop_scheduler._fire(token)
+                # No run dispatched.
+                assert recorder.calls == []
+                # Entry preserved (rearm scheduled in task group, not awaited here).
+                assert token in loop_scheduler._PENDING_BY_TOKEN
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_skips_when_session_alive(self, monkeypatch):
+        """Race avoidance — if the originating subprocess is alive, skip
+        and re-arm a redundancy retry."""
+        recorder = RunJobRecorder()
+        # Patch is_session_alive to claim our session is still alive.
+        from untether.runners import claude as claude_mod
+
+        monkeypatch.setattr(
+            claude_mod,
+            "is_session_alive",
+            lambda sid: sid == "sess-alive",
+        )
+        # Short redundancy interval so the retry-task cleanup is quick
+        # (default is 30s — would slow the test for no benefit).
+        monkeypatch.setattr(loop_scheduler, "_redundancy_check_interval", lambda: 0)
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = _register_simple_cron(chat_id=84, session_id="sess-alive")
+                await loop_scheduler._fire(token)
+                assert recorder.calls == []
+                # Entry preserved — redundancy retry scheduled.
+                assert token in loop_scheduler._PENDING_BY_TOKEN
+                # Cancel the entry so the redundancy retry exits immediately
+                # when it wakes up.
+                loop_scheduler.cancel_by_token(token)
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_dispatches_run_with_wrapped_prompt(self, monkeypatch):
+        recorder = RunJobRecorder()
+        from untether.runners import claude as claude_mod
+
+        monkeypatch.setattr(claude_mod, "is_session_alive", lambda _sid: False)
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = loop_scheduler.register_pending_wakeup(
+                    session_id="sess-fire",
+                    tool_use_id="t",
+                    delay_seconds=120,
+                    prompt="check the deploy",
+                    chat_id=85,
+                )
+                await loop_scheduler._fire(token)
+                assert len(recorder.calls) == 1
+                args = recorder.calls[0]
+                # Layout per at_scheduler._run_delayed (run_job 11-arg):
+                # (chat_id, message_id, prompt, resume_token, context,
+                #  thread_id, chat_session_key, reply_ref, on_thread_known,
+                #  engine_override, progress_ref)
+                assert args[0] == 85
+                assert "Loop iteration 1" in args[2]
+                assert "check the deploy" in args[2]
+                assert args[3] is not None
+                assert args[3].engine == "claude"
+                assert args[3].value == "sess-fire"
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_uses_fallback_for_sentinel_prompt(self, monkeypatch):
+        recorder = RunJobRecorder()
+        from untether.runners import claude as claude_mod
+
+        monkeypatch.setattr(claude_mod, "is_session_alive", lambda _sid: False)
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = loop_scheduler.register_pending_wakeup(
+                    session_id="s",
+                    tool_use_id="t",
+                    delay_seconds=120,
+                    prompt="<<autonomous-loop-dynamic>>",
+                    fallback_first_user_message="poll the build",
+                    chat_id=86,
+                )
+                await loop_scheduler._fire(token)
+                assert len(recorder.calls) == 1
+                wrapped = recorder.calls[0][2]
+                assert "poll the build" in wrapped
+                assert "<<autonomous-loop-dynamic>>" not in wrapped
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_fire_one_shot_wakeup_expires_after_fire(self, monkeypatch):
+        recorder = RunJobRecorder()
+        from untether.runners import claude as claude_mod
+
+        monkeypatch.setattr(claude_mod, "is_session_alive", lambda _sid: False)
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, recorder, FakeTransport(), 1)
+            try:
+                token = loop_scheduler.register_pending_wakeup(
+                    session_id="s",
+                    tool_use_id="t",
+                    delay_seconds=120,
+                    prompt="x",
+                    chat_id=87,
+                )
+                await loop_scheduler._fire(token)
+                # One-shot — expired after firing.
+                assert token not in loop_scheduler._PENDING_BY_TOKEN
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── Persistence ─────────────────────────────────────────────────────────
+
+
+class TestPersistence:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    async def test_register_writes_state_file(self, tmp_path: Path):
+        state_path = tmp_path / "active_loops.json"
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                _register_simple_cron(chat_id=200)
+                assert state_path.exists()
+                assert b'"entries"' in state_path.read_bytes()
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_restart_restores_pending_entries(self, tmp_path: Path):
+        state_path = tmp_path / "active_loops.json"
+        # First install: register one entry, persist.
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                token = loop_scheduler.register_pending_wakeup(
+                    session_id="sess-persisted",
+                    tool_use_id="t",
+                    delay_seconds=3600,
+                    prompt="long delay",
+                    chat_id=201,
+                )
+            finally:
+                tg.cancel_scope.cancel()
+        loop_scheduler.uninstall()
+
+        # Second install — must restore the entry from disk.
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                pending = loop_scheduler.pending_for_chat(201)
+                assert len(pending) == 1
+                assert pending[0].token == token
+                assert pending[0].prompt == "long delay"
+                assert pending[0].resume_token == "sess-persisted"
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_restart_skips_cancelled_entries(self, tmp_path: Path):
+        state_path = tmp_path / "active_loops.json"
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                token = _register_simple_cron(chat_id=202)
+                loop_scheduler.cancel_by_token(token)
+            finally:
+                tg.cancel_scope.cancel()
+        loop_scheduler.uninstall()
+
+        # Restart — cancelled entry should not be restored.
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                assert loop_scheduler.active_count() == 0
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_do_not_resume_persists_across_restart(self, tmp_path: Path):
+        state_path = tmp_path / "active_loops.json"
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                loop_scheduler.mark_do_not_resume("sess-blocked")
+            finally:
+                tg.cancel_scope.cancel()
+        loop_scheduler.uninstall()
+
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                assert loop_scheduler.is_do_not_resume("sess-blocked")
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_corrupt_state_file_is_ignored(self, tmp_path: Path):
+        state_path = tmp_path / "active_loops.json"
+        state_path.write_text("not valid json{{")
+        async with anyio.create_task_group() as tg:
+            # Should not raise.
+            loop_scheduler.install(
+                tg, _noop_run_job, FakeTransport(), 1, state_path=state_path
+            )
+            try:
+                assert loop_scheduler.active_count() == 0
+            finally:
+                tg.cancel_scope.cancel()
+
+    async def test_persistence_disabled_when_no_path(self):
+        """install(state_path=None) skips persistence — used by tests."""
+        async with anyio.create_task_group() as tg:
+            loop_scheduler.install(tg, _noop_run_job, FakeTransport(), 1)
+            try:
+                _register_simple_cron(chat_id=203)
+                # No file created anywhere; nothing to assert directly,
+                # but the call must not have raised on persist.
+                assert loop_scheduler.active_count() == 1
+            finally:
+                tg.cancel_scope.cancel()
+
+
+# ── do-not-resume sentinel ──────────────────────────────────────────────
+
+
+class TestDoNotResume:
+    @pytest.fixture(autouse=True)
+    def _cleanup(self):
+        loop_scheduler.uninstall()
+        yield
+        loop_scheduler.uninstall()
+
+    def test_mark_then_check(self):
+        loop_scheduler.mark_do_not_resume("sess-x")
+        assert loop_scheduler.is_do_not_resume("sess-x")
+
+    def test_unknown_session_returns_false(self):
+        assert not loop_scheduler.is_do_not_resume("never-marked")
+
+    def test_mark_is_idempotent(self):
+        loop_scheduler.mark_do_not_resume("sess-y")
+        loop_scheduler.mark_do_not_resume("sess-y")
+        assert loop_scheduler.is_do_not_resume("sess-y")
diff --git a/tests/test_meta_line.py b/tests/test_meta_line.py
index 5257e5b5..2f53dd1f 100644
--- a/tests/test_meta_line.py
+++ b/tests/test_meta_line.py
@@ -429,3 +429,96 @@ def test_gemini_auto_model(self) -> None:
     def test_neither_dir_nor_model(self) -> None:
         footer = self._render_footer("codex", meta=None, context_line=None)
         assert footer is None
+
+
+# ── #269 — MarkdownFormatter.refresh_from() hot-reload hook ───────────────
+
+
+class TestMarkdownFormatterRefresh:
+    """``MarkdownFormatter.refresh_from`` is the runner-bridge hook that
+    pushes a fresh ``ProgressSettings`` snapshot into the formatter on
+    every run, so editing ``[progress]`` in ``untether.toml`` applies on
+    the next message without restart (#269)."""
+
+    def test_refresh_updates_max_actions(self) -> None:
+        from untether.settings import ProgressSettings
+
+        formatter = MarkdownFormatter(max_actions=5)
+        formatter.refresh_from(ProgressSettings(max_actions=8))
+        assert formatter.max_actions == 8
+
+    def test_refresh_updates_verbosity(self) -> None:
+        from untether.settings import ProgressSettings
+
+        formatter = MarkdownFormatter(verbosity="compact")
+        formatter.refresh_from(ProgressSettings(verbosity="verbose"))
+        assert formatter.verbosity == "verbose"
+
+    def test_refresh_clamps_negative_max_actions_to_zero(self) -> None:
+        class _Stub:
+            max_actions = -3
+            verbosity = "compact"
+
+        formatter = MarkdownFormatter(max_actions=5)
+        formatter.refresh_from(_Stub())
+        assert formatter.max_actions == 0
+
+    def test_refresh_ignores_invalid_verbosity(self) -> None:
+        class _Stub:
+            max_actions = 5
+            verbosity = "garbage"
+
+        formatter = MarkdownFormatter(verbosity="compact")
+        formatter.refresh_from(_Stub())
+        # Stays on the original valid value rather than accepting nonsense.
+        assert formatter.verbosity == "compact"
+
+    def test_refresh_tolerates_missing_attributes(self) -> None:
+        class _Empty:
+            pass
+
+        formatter = MarkdownFormatter(max_actions=5, verbosity="compact")
+        formatter.refresh_from(_Empty())
+        assert formatter.max_actions == 5
+        assert formatter.verbosity == "compact"
+
+    def test_telegram_presenter_refresh_delegates_to_formatter(self) -> None:
+        from untether.settings import ProgressSettings
+        from untether.telegram.bridge import TelegramPresenter
+
+        formatter = MarkdownFormatter(max_actions=2, verbosity="compact")
+        presenter = TelegramPresenter(formatter=formatter)
+        presenter.refresh_progress_settings(
+            ProgressSettings(max_actions=9, verbosity="verbose")
+        )
+        assert formatter.max_actions == 9
+        assert formatter.verbosity == "verbose"
+
+
+def test_load_progress_settings_returns_defaults_when_missing(monkeypatch) -> None:
+    """``_load_progress_settings`` falls back to defaults when no config exists."""
+    from untether import runner_bridge
+    from untether.settings import ProgressSettings
+
+    monkeypatch.setattr(
+        "untether.settings.load_settings_if_exists",
+        lambda: None,
+    )
+    cfg = runner_bridge._load_progress_settings()
+    assert isinstance(cfg, ProgressSettings)
+
+
+def test_load_progress_settings_returns_defaults_on_error(monkeypatch) -> None:
+    """A settings-load exception falls back to defaults rather than raising."""
+    from untether import runner_bridge
+    from untether.settings import ProgressSettings
+
+    def _boom():
+        raise RuntimeError("disk full")
+
+    monkeypatch.setattr(
+        "untether.settings.load_settings_if_exists",
+        _boom,
+    )
+    cfg = runner_bridge._load_progress_settings()
+    assert isinstance(cfg, ProgressSettings)
diff --git a/tests/test_onboarding.py b/tests/test_onboarding.py
index fd73f218..3db43181 100644
--- a/tests/test_onboarding.py
+++ b/tests/test_onboarding.py
@@ -17,7 +17,13 @@ def test_check_setup_marks_missing_codex(monkeypatch, tmp_path: Path) -> None:
             UntetherSettings.model_validate(
                 {
                     "transport": "telegram",
-                    "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+                    "transports": {
+                        "telegram": {
+                            "bot_token": "token",
+                            "chat_id": 123,
+                            "allow_any_user": True,
+                        }
+                    },
                 }
             ),
             tmp_path / "untether.toml",
@@ -63,7 +69,13 @@ def _fail_require(*_args, **_kwargs):
             UntetherSettings.model_validate(
                 {
                     "transport": "telegram",
-                    "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+                    "transports": {
+                        "telegram": {
+                            "bot_token": "token",
+                            "chat_id": 123,
+                            "allow_any_user": True,
+                        }
+                    },
                 }
             ),
             tmp_path / "untether.toml",
diff --git a/tests/test_onboarding_interactive.py b/tests/test_onboarding_interactive.py
index c44972c2..f3433d3f 100644
--- a/tests/test_onboarding_interactive.py
+++ b/tests/test_onboarding_interactive.py
@@ -31,6 +31,7 @@ def test_render_config_escapes() -> None:
                 "telegram": {
                     "bot_token": 'token"with\\quote',
                     "chat_id": 123,
+                    "allow_any_user": True,
                 }
             },
         }
diff --git a/tests/test_pi_runner.py b/tests/test_pi_runner.py
index 40238655..e1d54940 100644
--- a/tests/test_pi_runner.py
+++ b/tests/test_pi_runner.py
@@ -266,6 +266,30 @@ def test_session_path_prefers_run_base_dir(tmp_path: Path) -> None:
 
     default_session_dir.assert_called_once_with(project_cwd)
     assert str(session_root) in session_path
+    # #207: session dir is created with restrictive perms so other users on
+    # shared hosts can't read Pi session JSONL.
+    assert session_root.exists()
+    assert (session_root.stat().st_mode & 0o777) == 0o700
+
+
+def test_session_path_tightens_existing_dir_perms(tmp_path: Path) -> None:
+    """#207: pre-existing dir with looser perms gets chmod'd to 0o700."""
+    runner = PiRunner(extra_args=[], model=None, provider=None)
+    project_cwd = Path("/project")
+    session_root = tmp_path / "sessions"
+    session_root.mkdir(mode=0o755)
+    assert (session_root.stat().st_mode & 0o777) == 0o755
+
+    with (
+        patch("untether.runners.pi.get_run_base_dir", return_value=project_cwd),
+        patch(
+            "untether.runners.pi._default_session_dir",
+            return_value=session_root,
+        ),
+    ):
+        runner._new_session_path()
+
+    assert (session_root.stat().st_mode & 0o777) == 0o700
 
 
 def test_session_path_sanitizes_windows_separators() -> None:
diff --git a/tests/test_ping_command.py b/tests/test_ping_command.py
index d50a17be..fb9397a9 100644
--- a/tests/test_ping_command.py
+++ b/tests/test_ping_command.py
@@ -153,3 +153,33 @@ async def test_ping_default_chat_fallback_matches_unscoped_triggers() -> None:
         _make_ctx(chat_id=555, trigger_manager=mgr, default_chat_id=555)
     )
     assert "\u23f0 triggers: 1 cron (any," in result.text
+
+
+# ── #294: master pause indicator ──────────────────────────────────────
+
+
+@pytest.mark.anyio
+async def test_ping_paused_indicator() -> None:
+    """When the trigger manager is paused, /ping uses the ⏸ prefix."""
+    mgr = _make_manager(
+        crons=[{"id": "a", "schedule": "0 9 * * *", "prompt": "x", "chat_id": 10}]
+    )
+    mgr.pause()
+    result = await BACKEND.handle(_make_ctx(chat_id=10, trigger_manager=mgr))
+    assert "⏸ triggers paused" in result.text
+    assert "(suspended)" in result.text
+    # Active prefix must NOT appear (no double-rendering).
+    assert "⏰ triggers:" not in result.text
+
+
+@pytest.mark.anyio
+async def test_ping_resumed_indicator() -> None:
+    """After resume, /ping returns to the active prefix."""
+    mgr = _make_manager(
+        crons=[{"id": "a", "schedule": "0 9 * * *", "prompt": "x", "chat_id": 10}]
+    )
+    mgr.pause()
+    mgr.resume()
+    result = await BACKEND.handle(_make_ctx(chat_id=10, trigger_manager=mgr))
+    assert "⏰ triggers:" in result.text
+    assert "⏸ triggers paused" not in result.text
diff --git a/tests/test_preamble.py b/tests/test_preamble.py
index 4c916e78..b8c03c9b 100644
--- a/tests/test_preamble.py
+++ b/tests/test_preamble.py
@@ -4,7 +4,15 @@
 
 from unittest.mock import patch
 
-from untether.runner_bridge import _DEFAULT_PREAMBLE, _apply_preamble
+from untether.runner_bridge import (
+    _DEFAULT_PREAMBLE,
+    _apply_preamble,
+)
+from untether.runners.claude import (
+    _PREPEND_BODY_CAP,
+    _PREPEND_LENGTH_GATE,
+    _prepend_exitplanmode_plan,
+)
 from untether.settings import PreambleSettings
 
 
@@ -54,3 +62,159 @@ def test_default_preamble_includes_outbox_instructions() -> None:
     """Default preamble tells agents about the .untether-outbox/ delivery mechanism."""
     assert ".untether-outbox/" in _DEFAULT_PREAMBLE
     assert "/file get" in _DEFAULT_PREAMBLE
+
+
+# ───── #508 / #515 — plan-mode preamble clauses ────────────────────────
+
+
+def test_default_preamble_has_exitplanmode_plan_body_clause() -> None:
+    """A1 (#515 tuning): ExitPlanMode plan body must be a concise 3-5
+    bullet summary - never just a file path, but also not an expanded
+    substantive summary (rc11 over-fire). The plan is shown for
+    approval, not as the final deliverable."""
+    assert "ExitPlanMode" in _DEFAULT_PREAMBLE
+    assert "concise 3–5 bullet" in _DEFAULT_PREAMBLE
+    assert "never just a file path" in _DEFAULT_PREAMBLE
+    assert "shown to the user for approval, not as the final deliverable" in (
+        _DEFAULT_PREAMBLE
+    )
+
+
+def test_default_preamble_has_post_approval_brief_summary_clause() -> None:
+    """A2 (#515 tuning): After ExitPlanMode is approved, the final
+    Telegram message should be a brief CLI-style summary (3-7 bullets
+    or 1-2 short paragraphs, ~500-1500 chars). Do NOT re-paste the full
+    plan content - rc11 told Claude to "repeat substantive findings"
+    which produced 30k-char finals."""
+    assert "After `ExitPlanMode` is approved" in _DEFAULT_PREAMBLE
+    assert "brief CLI-style summary" in _DEFAULT_PREAMBLE
+    assert "3–7 bullets" in _DEFAULT_PREAMBLE
+    assert "Do NOT re-paste the full plan content" in _DEFAULT_PREAMBLE
+    assert "~500–1500 characters" in _DEFAULT_PREAMBLE
+
+
+def test_default_preamble_summary_block_asks_for_headline_summary() -> None:
+    """A3 (#515 tuning): the ## Summary block's Plan/Document Created
+    bullet asks for a pointer + 3-5 bullet headline summary, not a
+    re-paste of the full plan content. The user already saw the plan
+    during approval."""
+    assert "3–5 bullet headline summary" in _DEFAULT_PREAMBLE
+    assert "not a re-paste of the full content" in _DEFAULT_PREAMBLE
+
+
+def test_default_preamble_does_not_drive_verbose_post_approval_text() -> None:
+    """Regression for #515: ensure the rc11 verbosity-driving phrases
+    that produced 42k-char Telegram finals are no longer present."""
+    # rc11 A2 phrase that told Claude to repeat the full content
+    assert "MUST repeat the substantive findings or decisions" not in (
+        _DEFAULT_PREAMBLE
+    )
+    # rc11 A1 phrase that told Claude to expand bullets into a
+    # substantive summary for research/audit tasks
+    assert "expand the bullets into a substantive summary" not in _DEFAULT_PREAMBLE
+    # rc11 A3 phrase that told Claude to put full findings inline
+    assert "do not require the user to open the file" not in _DEFAULT_PREAMBLE
+
+
+# ───── #508 / #515 Layer E — _prepend_exitplanmode_plan helper ─────────
+
+
+def test_prepend_exitplanmode_plan_when_final_answer_short() -> None:
+    """The original #508 repro: post-approval result is brief (584
+    chars in the live capture). Plan body must be prepended so the user
+    sees the substantive findings in chat."""
+    plan = "- Finding 1\n- Finding 2\n- Recommend X"
+    short_final = "Plan approved — research is complete. See file."
+    assert len(short_final) < _PREPEND_LENGTH_GATE
+
+    result = _prepend_exitplanmode_plan(short_final, plan)
+
+    assert "📋 Plan (approved):" in result
+    assert plan in result
+    assert short_final in result
+    # Plan body comes before the brief acknowledgement (separator)
+    assert result.index(plan) < result.index(short_final)
+
+
+def test_prepend_exitplanmode_plan_skipped_when_answer_substantive() -> None:
+    """#515: when the post-approval text is ≥ ``_PREPEND_LENGTH_GATE``
+    chars (Claude wrote a real CLI-style summary), do NOT prepend the
+    plan body — the post-approval text is doing the job. This is the
+    load-bearing change vs rc11/rc12 where the substring check failed
+    on paraphrased summaries and double-shipped content."""
+    plan = "- Finding 1\n- Finding 2\n- Recommend X"
+    substantive_final = (
+        "I investigated the issue and here is what I found:\n\n"
+        "- Headline 1: module X had a regression introduced in commit abc123\n"
+        "- Headline 2: the root cause was a missing null guard in the parser\n"
+        "- Headline 3: rolled back commit abc123 and added a regression test\n"
+        "- Headline 4: next step is to backfill the affected rows Monday\n\n"
+        "Decisions made: kept the legacy code path for one more release cycle to\n"
+        "give downstream consumers time to migrate; full removal scheduled for the\n"
+        "next minor version once telemetry confirms zero active callers.\n\n"
+        "Next steps: open a follow-up issue for the backfill, send a heads-up in\n"
+        "the team channel, and re-run the daily-audit cron tomorrow morning to\n"
+        "confirm the regression is gone from the verification window.\n"
+    )
+    assert len(substantive_final) >= _PREPEND_LENGTH_GATE
+
+    result = _prepend_exitplanmode_plan(substantive_final, plan)
+
+    assert result == substantive_final
+    assert "📋 Plan (approved):" not in result
+
+
+def test_prepend_exitplanmode_plan_caps_long_plan_body() -> None:
+    """#515: when Layer E does fire and the captured plan body is
+    longer than ``_PREPEND_BODY_CAP``, truncate it to avoid runaway
+    finals. Live staging captures had 5,000-char plan bodies that got
+    prepended in full."""
+    plan = "x" * (_PREPEND_BODY_CAP + 1000)
+    short_final = "ok"
+
+    result = _prepend_exitplanmode_plan(short_final, plan)
+
+    assert "📋 Plan (approved):" in result
+    assert "plan truncated" in result
+    # Plan body in the result should be ~_PREPEND_BODY_CAP chars (plus
+    # the truncation suffix), not the full 2500-char original.
+    assert "x" * (_PREPEND_BODY_CAP + 100) not in result
+
+
+def test_prepend_exitplanmode_plan_skipped_when_already_substring() -> None:
+    """Secondary skip rule: when the plan body is a literal substring
+    of the final answer (rare with rc13 wording, but a cheap belt-and-
+    braces check), do not prepend."""
+    plan = "- Finding 1\n- Finding 2"
+    final = "Here is what I found:\n- Finding 1\n- Finding 2\n\nNext steps: ..."
+    assert len(final) < _PREPEND_LENGTH_GATE
+
+    result = _prepend_exitplanmode_plan(final, plan)
+
+    assert result == final
+    assert "📋 Plan (approved):" not in result
+
+
+def test_prepend_exitplanmode_plan_skipped_when_no_plan_body() -> None:
+    """No plan body captured → return the final answer unchanged."""
+    final = "ok"
+    assert _prepend_exitplanmode_plan(final, None) == final
+    assert _prepend_exitplanmode_plan(final, "") == final
+    assert _prepend_exitplanmode_plan(final, "   \n\t") == final
+
+
+def test_prepend_exitplanmode_plan_handles_empty_final_answer() -> None:
+    """If the post-approval result yields an entirely empty final answer
+    (no fallback text either), the plan body becomes the full answer."""
+    plan = "- Finding 1"
+    result = _prepend_exitplanmode_plan("", plan)
+    assert result.startswith("📋 Plan (approved):")
+    assert plan in result
+
+
+def test_prepend_exitplanmode_plan_handles_none_final_answer() -> None:
+    """None ``final_answer`` is handled the same as empty string."""
+    plan = "- Finding 1"
+    result = _prepend_exitplanmode_plan(None, plan)
+    assert "📋 Plan (approved):" in result
+    assert plan in result
diff --git a/tests/test_projects_config.py b/tests/test_projects_config.py
index bdcbbe86..61d641ce 100644
--- a/tests/test_projects_config.py
+++ b/tests/test_projects_config.py
@@ -9,7 +9,11 @@
 
 
 def _base_config() -> dict:
-    return {"transports": {"telegram": {"bot_token": "token", "chat_id": 123}}}
+    return {
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        }
+    }
 
 
 def test_parse_projects_skips_engine_alias() -> None:
@@ -38,7 +42,7 @@ def test_init_writes_project(monkeypatch, tmp_path) -> None:
     config_path = tmp_path / "untether.toml"
     config_path.write_text(
         'transport = "telegram"\n\n[transports.telegram]\n'
-        'bot_token = "token"\nchat_id = 123\n',
+        'bot_token = "token"\nchat_id = 123\nallow_any_user = true\n',
         encoding="utf-8",
     )
     monkeypatch.setattr("untether.config.HOME_CONFIG_PATH", config_path)
@@ -62,7 +66,10 @@ def test_init_writes_project(monkeypatch, tmp_path) -> None:
 
 def test_init_migrates_legacy_config(monkeypatch, tmp_path) -> None:
     config_path = tmp_path / "untether.toml"
-    config_path.write_text('bot_token = "token"\nchat_id = 123\n', encoding="utf-8")
+    config_path.write_text(
+        'bot_token = "token"\nchat_id = 123\nallow_any_user = true\n',
+        encoding="utf-8",
+    )
     monkeypatch.setattr("untether.config.HOME_CONFIG_PATH", config_path)
     monkeypatch.setattr(cli, "resolve_default_base", lambda _: "main")
     monkeypatch.setattr(cli, "_load_settings_optional", lambda: (None, None))
@@ -100,7 +107,9 @@ def test_projects_skips_unknown_engine() -> None:
 
 def test_projects_skips_chat_id_matching_transport() -> None:
     config = {
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
         "projects": {"z80": {"path": "/tmp/repo", "chat_id": 123}},
     }
     settings = UntetherSettings.model_validate(config)
@@ -114,7 +123,9 @@ def test_projects_skips_chat_id_matching_transport() -> None:
 
 def test_projects_skips_duplicate_chat_id() -> None:
     config = {
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
         "projects": {
             "a": {"path": "/tmp/a", "chat_id": -10},
             "b": {"path": "/tmp/b", "chat_id": -10},
diff --git a/tests/test_runner_utils.py b/tests/test_runner_utils.py
index 89076beb..53ee67c2 100644
--- a/tests/test_runner_utils.py
+++ b/tests/test_runner_utils.py
@@ -393,6 +393,62 @@ async def fake_drain_stderr(*args: Any, **kwargs: Any) -> None:
     assert any(isinstance(evt, CompletedEvent) for evt in events)
 
 
+@pytest.mark.anyio
+async def test_runner_start_log_has_no_prompt_content(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """#205: prompt content stays at DEBUG; INFO `runner.start` carries length only."""
+    from structlog.testing import capture_logs
+
+    class _FakeProc:
+        def __init__(self) -> None:
+            self.stdout = object()
+            self.stderr = object()
+            self.stdin = None
+            self.pid = 999
+
+        async def wait(self) -> int:
+            return 0
+
+    class _FakeManager:
+        def __init__(self, proc: _FakeProc) -> None:
+            self._proc = proc
+
+        async def __aenter__(self) -> _FakeProc:
+            return self._proc
+
+        async def __aexit__(self, exc_type, exc, tb) -> None:
+            return None
+
+    proc = _FakeProc()
+
+    def fake_manage_subprocess(*args: Any, **kwargs: Any) -> _FakeManager:
+        _ = args, kwargs
+        return _FakeManager(proc)
+
+    async def fake_drain_stderr(*args: Any, **kwargs: Any) -> None:
+        _ = args, kwargs
+        return
+
+    monkeypatch.setattr(runner_module, "manage_subprocess", fake_manage_subprocess)
+    monkeypatch.setattr(runner_module, "drain_stderr", fake_drain_stderr)
+
+    runner = _RunJsonlRunner()
+    secret_prompt = "API_KEY=sk-abc1234567890ABCDEFGH and run my task"
+    with capture_logs() as logs:
+        _ = [evt async for evt in runner.run_impl(secret_prompt, None)]
+
+    start_events = [r for r in logs if r.get("event") == "runner.start"]
+    assert start_events, "runner.start event must fire"
+    for record in start_events:
+        # Prompt content must NOT appear in the INFO log under any key.
+        assert "prompt" not in record
+        assert "prompt_preview" not in record
+        # But length should be there for ops visibility.
+        assert record.get("prompt_len") == len(secret_prompt)
+        assert "API_KEY" not in str(record)
+
+
 @pytest.mark.anyio
 async def test_jsonl_run_impl_branches(monkeypatch: pytest.MonkeyPatch) -> None:
     class _FakeProc:
@@ -665,3 +721,64 @@ def test_stderr_excerpt_applies_sanitisation(self) -> None:
         assert result is not None
         assert "/home/user" not in result
         assert "[path]" in result
+
+    def test_redacts_macos_user_path(self) -> None:
+        # #208: macOS uses /Users/<user>/...
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("Error at /Users/alice/Library/foo.log:42")
+        assert "/Users/alice" not in result
+        assert "[path]" in result
+        assert ":42" in result  # line marker survives
+
+    def test_redacts_macos_private_var(self) -> None:
+        # #208: macOS temp lives under /private/var/folders/...
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("/private/var/folders/abc/T/run.log: not found")
+        assert "/private/var" not in result
+        assert "[path]" in result
+
+    def test_redacts_tmp_path(self) -> None:
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("Failed to open /tmp/run-xyz.lock")
+        assert "/tmp" not in result
+        assert "[path]" in result
+
+    def test_redacts_var_log_path(self) -> None:
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("See /var/log/journal/system.log for details")
+        assert "/var/log" not in result
+        assert "[path]" in result
+
+    def test_redacts_container_workspace_path(self) -> None:
+        # #208: container conventions (/app, /workspace).
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("Crash in /app/main.py and /workspace/src/lib.py")
+        assert "/app/main.py" not in result
+        assert "/workspace" not in result
+        assert result.count("[path]") >= 2
+
+    def test_redacts_root_home(self) -> None:
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("Permission denied at /root/.ssh/id_rsa")
+        assert "/root" not in result
+        assert "[path]" in result
+
+    def test_redacts_etc_path(self) -> None:
+        from untether.runner import _sanitise_stderr
+
+        result = _sanitise_stderr("Could not parse /etc/untether/config.toml")
+        assert "/etc/untether" not in result
+        assert "[path]" in result
+
+    def test_preserves_short_root_segments(self) -> None:
+        # Sanity: bare `/x` or `/y` (no segment) must NOT trigger [path].
+        from untether.runner import _sanitise_stderr
+
+        text = "Use option /x to enable verbose mode"
+        assert _sanitise_stderr(text) == text
diff --git a/tests/test_runtime_loader.py b/tests/test_runtime_loader.py
index afae0e7c..83256ff2 100644
--- a/tests/test_runtime_loader.py
+++ b/tests/test_runtime_loader.py
@@ -15,7 +15,13 @@ def test_build_runtime_spec_minimal(
         {
             "transport": "telegram",
             "watch_config": True,
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     config_path = tmp_path / "untether.toml"
@@ -40,7 +46,13 @@ def test_resolve_default_engine_unknown(tmp_path: Path) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     with pytest.raises(ConfigError, match="Unknown default engine"):
diff --git a/tests/test_session_stats.py b/tests/test_session_stats.py
index 8c92ccea..fe726311 100644
--- a/tests/test_session_stats.py
+++ b/tests/test_session_stats.py
@@ -161,3 +161,100 @@ def test_store_aggregate_all_period(tmp_path) -> None:
     assert len(stats) == 1
     assert stats[0].run_count == 3
     assert stats[0].action_count == 15
+
+
+# ── #271 Tier 3: triggered/manual breakdown ────────────────────────────────
+
+
+def test_day_bucket_record_manual_default() -> None:
+    bucket = DayBucket()
+    bucket.record(actions=1, duration_ms=100)
+    assert bucket.manual_count == 1
+    assert bucket.triggered_count == 0
+
+
+def test_day_bucket_record_triggered() -> None:
+    bucket = DayBucket()
+    bucket.record(actions=1, duration_ms=100, triggered=True)
+    assert bucket.triggered_count == 1
+    assert bucket.manual_count == 0
+
+
+def test_day_bucket_mixed_records_split() -> None:
+    bucket = DayBucket()
+    bucket.record(actions=1, duration_ms=100, triggered=True)
+    bucket.record(actions=1, duration_ms=100)
+    bucket.record(actions=1, duration_ms=100, triggered=True)
+    assert bucket.run_count == 3
+    assert bucket.triggered_count == 2
+    assert bucket.manual_count == 1
+
+
+def test_day_bucket_roundtrip_includes_breakdown() -> None:
+    bucket = DayBucket(
+        run_count=3,
+        action_count=10,
+        duration_ms=5000,
+        last_run_ts=1000.0,
+        triggered_count=2,
+        manual_count=1,
+    )
+    restored = DayBucket.from_dict(bucket.to_dict())
+    assert restored.triggered_count == 2
+    assert restored.manual_count == 1
+
+
+def test_day_bucket_from_dict_old_format_defaults_zero() -> None:
+    """Old stats.json files (pre-#271) lack triggered_count/manual_count."""
+    legacy = {
+        "run_count": 5,
+        "action_count": 25,
+        "duration_ms": 10000,
+        "last_run_ts": 1000.0,
+    }
+    restored = DayBucket.from_dict(legacy)
+    assert restored.run_count == 5
+    assert restored.triggered_count == 0
+    assert restored.manual_count == 0
+
+
+def test_store_record_run_triggered_kwarg(tmp_path) -> None:
+    store = SessionStatsStore(tmp_path / "stats.json")
+    store.record_run("claude", actions=1, duration_ms=100, triggered=True)
+    store.record_run("claude", actions=1, duration_ms=100)
+    stats = store.aggregate(period="today")
+    assert len(stats) == 1
+    assert stats[0].triggered_count == 1
+    assert stats[0].manual_count == 1
+
+
+def test_store_aggregate_sums_triggered_and_manual(tmp_path) -> None:
+    store = SessionStatsStore(tmp_path / "stats.json")
+    # Inject two days for the same engine.
+    store._data = {
+        "version": 1,
+        "engines": {
+            "claude": {
+                "2026-03-01": DayBucket(
+                    run_count=2,
+                    action_count=4,
+                    duration_ms=2000,
+                    last_run_ts=1000.0,
+                    triggered_count=1,
+                    manual_count=1,
+                ).to_dict(),
+                "2026-03-04": DayBucket(
+                    run_count=3,
+                    action_count=6,
+                    duration_ms=3000,
+                    last_run_ts=2000.0,
+                    triggered_count=2,
+                    manual_count=1,
+                ).to_dict(),
+            }
+        },
+    }
+    stats = store.aggregate(period="all")
+    assert len(stats) == 1
+    assert stats[0].triggered_count == 3
+    assert stats[0].manual_count == 2
diff --git a/tests/test_settings.py b/tests/test_settings.py
index f092ca2a..1a63e954 100644
--- a/tests/test_settings.py
+++ b/tests/test_settings.py
@@ -21,6 +21,7 @@ def test_load_settings_from_toml(tmp_path: Path) -> None:
         "[transports.telegram]\n"
         'bot_token = "token"\n'
         "chat_id = 123\n\n"
+        "allow_any_user = true\n"
         "[codex]\n"
         'model = "gpt-4"\n',
         encoding="utf-8",
@@ -51,7 +52,8 @@ def test_env_overrides_toml(tmp_path: Path, monkeypatch) -> None:
         'transport = "telegram"\n\n'
         "[transports.telegram]\n"
         'bot_token = "token"\n'
-        "chat_id = 123\n",
+        "chat_id = 123\n"
+        "allow_any_user = true\n",
         encoding="utf-8",
     )
     monkeypatch.setenv("UNTETHER__DEFAULT_ENGINE", "claude")
@@ -63,7 +65,10 @@ def test_env_overrides_toml(tmp_path: Path, monkeypatch) -> None:
 
 def test_legacy_keys_migrated(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
-    config_path.write_text('bot_token = "token"\nchat_id = 123\n', encoding="utf-8")
+    config_path.write_text(
+        'bot_token = "token"\nchat_id = 123\nallow_any_user = true\n',
+        encoding="utf-8",
+    )
 
     settings, loaded_path = load_settings(config_path)
 
@@ -81,7 +86,9 @@ def test_validate_settings_data_rejects_invalid_bot_token_type(tmp_path: Path) -
     config_path = tmp_path / "untether.toml"
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": 123, "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": 123, "chat_id": 123, "allow_any_user": True}
+        },
     }
 
     with pytest.raises(ConfigError, match="bot_token"):
@@ -93,7 +100,9 @@ def test_validate_settings_data_rejects_empty_default_engine(tmp_path: Path) ->
     data = {
         "default_engine": "   ",
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
     }
 
     with pytest.raises(ConfigError, match="default_engine"):
@@ -104,7 +113,9 @@ def test_validate_settings_data_rejects_empty_default_project(tmp_path: Path) ->
     config_path = tmp_path / "untether.toml"
     data = {
         "default_project": "   ",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
     }
 
     with pytest.raises(ConfigError, match="default_project"):
@@ -115,7 +126,9 @@ def test_validate_settings_data_rejects_empty_project_path(tmp_path: Path) -> No
     config_path = tmp_path / "untether.toml"
     data = {
         "projects": {"z80": {"path": "   "}},
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
     }
 
     with pytest.raises(ConfigError, match="path"):
@@ -127,7 +140,13 @@ def test_engine_config_none_and_invalid(tmp_path: Path) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
             "codex": None,
         }
     )
@@ -136,7 +155,13 @@ def test_engine_config_none_and_invalid(tmp_path: Path) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
             "codex": "nope",
         }
     )
@@ -149,7 +174,13 @@ def test_transport_config_telegram_and_extra(tmp_path: Path) -> None:
     settings = UntetherSettings.model_validate(
         {
             "transport": "telegram",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     telegram = settings.transport_config("telegram", config_path=config_path)
@@ -161,7 +192,11 @@ def test_transport_config_telegram_and_extra(tmp_path: Path) -> None:
         {
             "transport": "telegram",
             "transports": {
-                "telegram": {"bot_token": "token", "chat_id": 123},
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                },
                 "discord": None,
             },
         }
@@ -172,7 +207,11 @@ def test_transport_config_telegram_and_extra(tmp_path: Path) -> None:
         {
             "transport": "telegram",
             "transports": {
-                "telegram": {"bot_token": "token", "chat_id": 123},
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                },
                 "discord": "nope",
             },
         }
@@ -185,18 +224,245 @@ def test_bot_token_none_rejected(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": None, "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": None, "chat_id": 123, "allow_any_user": True}
+        },
     }
     with pytest.raises(ConfigError, match="bot_token"):
         validate_settings_data(data, config_path=config_path)
 
 
+def test_voice_transcription_api_key_is_secret_str(tmp_path: Path) -> None:
+    """#378: voice_transcription_api_key must be SecretStr — masks repr()/str()
+    and only yields the raw value via .get_secret_value()."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        "[transports.telegram]\n"
+        'bot_token = "tok"\n'
+        "chat_id = 123\n"
+        "allow_any_user = true\n"
+        "voice_transcription = true\n"
+        'voice_transcription_api_key = "sk-supersecret-1234567890ABCDEF"\n',
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    key = settings.transports.telegram.voice_transcription_api_key
+    assert key is not None
+    assert key.get_secret_value() == "sk-supersecret-1234567890ABCDEF"
+    # Masking: str() and repr() must not leak the value.
+    assert "supersecret" not in str(key)
+    assert "supersecret" not in repr(key)
+
+
+def test_voice_transcription_api_key_empty_string_normalised_to_none(
+    tmp_path: Path,
+) -> None:
+    """#378: empty/whitespace-only API key round-trips to None so downstream
+    truthy / `is not None` checks behave the same as with the prior
+    `NonEmptyStr | None` field type."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        "[transports.telegram]\n"
+        'bot_token = "tok"\n'
+        "chat_id = 123\n"
+        "allow_any_user = true\n"
+        'voice_transcription_api_key = "   "\n',
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.transports.telegram.voice_transcription_api_key is None
+
+
+def test_voice_transcription_api_key_default_none(tmp_path: Path) -> None:
+    """#378: default is still None when key is omitted."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allow_any_user = true\n",
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.transports.telegram.voice_transcription_api_key is None
+
+
+# ───────────────────────────────────────────────────────────────────────────
+# #409 — env allowlist user-extensible config (SecuritySettings extras)
+# ───────────────────────────────────────────────────────────────────────────
+
+
+def test_env_extra_allow_round_trip(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allow_any_user = true\n\n"
+        "[security]\n"
+        'env_extra_allow = ["OP_SERVICE_ACCOUNT_TOKEN", "DOPPLER_TOKEN"]\n'
+        'env_extra_prefix_allow = ["VAULT_", "INFISICAL_"]\n',
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.security.env_extra_allow == [
+        "OP_SERVICE_ACCOUNT_TOKEN",
+        "DOPPLER_TOKEN",
+    ]
+    assert settings.security.env_extra_prefix_allow == ["VAULT_", "INFISICAL_"]
+
+
+def test_env_extra_allow_default_empty(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allow_any_user = true\n",
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.security.env_extra_allow == []
+    assert settings.security.env_extra_prefix_allow == []
+
+
+def test_env_extra_allow_rejects_empty_string(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n\n'
+        "[security]\n"
+        'env_extra_allow = [""]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_allow"):
+        load_settings(config_path)
+
+
+def test_env_extra_allow_rejects_whitespace_only(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n\n'
+        "[security]\n"
+        'env_extra_allow = ["   "]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_allow"):
+        load_settings(config_path)
+
+
+def test_env_extra_allow_rejects_lowercase(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n\n'
+        "[security]\n"
+        'env_extra_allow = ["my_token"]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_allow"):
+        load_settings(config_path)
+
+
+def test_env_extra_allow_rejects_leading_digit(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n\n'
+        "[security]\n"
+        'env_extra_allow = ["1_BAD"]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_allow"):
+        load_settings(config_path)
+
+
+def test_env_extra_allow_rejects_spaces(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n\n'
+        "[security]\n"
+        'env_extra_allow = ["TOK EN"]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_allow"):
+        load_settings(config_path)
+
+
+def test_env_extra_prefix_allow_validates_names(tmp_path: Path) -> None:
+    """Prefix entries must match the same env-var name shape."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allow_any_user = true\n\n"
+        "[security]\n"
+        'env_extra_prefix_allow = ["bad-prefix"]\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="env_extra_prefix_allow"):
+        load_settings(config_path)
+
+
+# ───────────────────────────────────────────────────────────────────────────
+# #377 — startup-block on empty `allowed_user_ids` (insecure default)
+# ───────────────────────────────────────────────────────────────────────────
+
+
+def test_empty_allowed_users_blocks_startup(tmp_path: Path) -> None:
+    """#377: empty allowlist + no opt-out is a hard ConfigError at load time."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n',
+        encoding="utf-8",
+    )
+    with pytest.raises(ConfigError, match="allowed_user_ids is empty"):
+        load_settings(config_path)
+
+
+def test_allow_any_user_overrides_block(tmp_path: Path) -> None:
+    """#377: explicit `allow_any_user = true` lets the empty allowlist load."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allow_any_user = true\n",
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.transports.telegram.allowed_user_ids == []
+    assert settings.transports.telegram.allow_any_user is True
+
+
+def test_non_empty_allowed_users_loads(tmp_path: Path) -> None:
+    """#377: a populated allowlist loads without needing the opt-out."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allowed_user_ids = [42, 99]\n",
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.transports.telegram.allowed_user_ids == [42, 99]
+    assert settings.transports.telegram.allow_any_user is False
+
+
+def test_allow_any_user_with_populated_allowlist_still_loads(tmp_path: Path) -> None:
+    """#377: setting both is fine — the validator is only there to prevent the
+    silent insecure default of empty + False."""
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        '[transports.telegram]\nbot_token = "tok"\nchat_id = 123\n'
+        "allowed_user_ids = [42]\n"
+        "allow_any_user = true\n",
+        encoding="utf-8",
+    )
+    settings, _ = load_settings(config_path)
+    assert settings.transports.telegram.allowed_user_ids == [42]
+    assert settings.transports.telegram.allow_any_user is True
+
+
 def test_require_telegram_rejects_non_telegram_transport(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
     settings = UntetherSettings.model_validate(
         {
             "transport": "discord",
-            "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "token",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
     with pytest.raises(ConfigError, match="Unsupported transport"):
@@ -218,7 +484,7 @@ def test_load_settings_if_exists_loads(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
     config_path.write_text(
         'transport = "telegram"\n\n[transports.telegram]\n'
-        'bot_token = "token"\nchat_id = 123\n',
+        'bot_token = "token"\nchat_id = 123\nallow_any_user = true\n',
         encoding="utf-8",
     )
 
@@ -262,6 +528,7 @@ def test_footer_from_toml(tmp_path: Path) -> None:
         "[transports.telegram]\n"
         'bot_token = "token"\n'
         "chat_id = 123\n\n"
+        "allow_any_user = true\n"
         "[footer]\n"
         "show_api_cost = false\n"
         "show_subscription_usage = true\n",
@@ -277,7 +544,9 @@ def test_footer_rejects_extra_keys(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
         "footer": {"show_api_cost": True, "bogus_key": True},
     }
     with pytest.raises(ConfigError, match="bogus_key"):
@@ -304,6 +573,7 @@ def test_preamble_from_toml(tmp_path: Path) -> None:
         "[transports.telegram]\n"
         'bot_token = "token"\n'
         "chat_id = 123\n\n"
+        "allow_any_user = true\n"
         "[preamble]\n"
         "enabled = false\n"
         'text = "Custom preamble"\n',
@@ -319,7 +589,9 @@ def test_preamble_rejects_extra_keys(tmp_path: Path) -> None:
     config_path = tmp_path / "untether.toml"
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "token", "chat_id": 123}},
+        "transports": {
+            "telegram": {"bot_token": "token", "chat_id": 123, "allow_any_user": True}
+        },
         "preamble": {"enabled": True, "bogus_key": True},
     }
     with pytest.raises(ConfigError, match="bogus_key"):
@@ -334,7 +606,9 @@ def test_preamble_rejects_extra_keys(tmp_path: Path) -> None:
 def test_progress_min_render_interval_defaults(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
     }
     settings = validate_settings_data(data, config_path=tmp_path / "c.toml")
     assert settings.progress.min_render_interval == 2.0
@@ -343,7 +617,9 @@ def test_progress_min_render_interval_defaults(tmp_path: Path) -> None:
 def test_progress_group_chat_rps_defaults(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
     }
     settings = validate_settings_data(data, config_path=tmp_path / "c.toml")
     assert settings.progress.group_chat_rps == pytest.approx(20.0 / 60.0)
@@ -352,7 +628,9 @@ def test_progress_group_chat_rps_defaults(tmp_path: Path) -> None:
 def test_progress_min_render_interval_custom(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
         "progress": {"min_render_interval": 5.0},
     }
     settings = validate_settings_data(data, config_path=tmp_path / "c.toml")
@@ -362,7 +640,9 @@ def test_progress_min_render_interval_custom(tmp_path: Path) -> None:
 def test_progress_group_chat_rps_custom(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
         "progress": {"group_chat_rps": 0.5},
     }
     settings = validate_settings_data(data, config_path=tmp_path / "c.toml")
@@ -372,7 +652,9 @@ def test_progress_group_chat_rps_custom(tmp_path: Path) -> None:
 def test_progress_min_render_interval_rejects_negative(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
         "progress": {"min_render_interval": -1.0},
     }
     with pytest.raises(ConfigError):
@@ -382,7 +664,9 @@ def test_progress_min_render_interval_rejects_negative(tmp_path: Path) -> None:
 def test_progress_group_chat_rps_rejects_zero(tmp_path: Path) -> None:
     data = {
         "transport": "telegram",
-        "transports": {"telegram": {"bot_token": "tok", "chat_id": 1}},
+        "transports": {
+            "telegram": {"bot_token": "tok", "chat_id": 1, "allow_any_user": True}
+        },
         "progress": {"group_chat_rps": 0},
     }
     with pytest.raises(ConfigError):
@@ -500,3 +784,97 @@ def test_watchdog_prespawn_ram_bounds() -> None:
         WatchdogSettings(prespawn_ram_warn_mb=-1)
     with pytest.raises(ValidationError):
         WatchdogSettings(prespawn_ram_block_mb=65537)
+
+
+# ---------------------------------------------------------------------------
+# LoopSettings (#289) — Untether-side observation of /loop / ScheduleWakeup
+
+
+def test_loop_settings_defaults_off() -> None:
+    """[loop] is opt-in; default state is exactly the v0.35.3 behaviour."""
+
+    from untether.settings import LoopSettings
+
+    s = LoopSettings()
+    assert s.enabled is False
+    assert s.inline_threshold_seconds == 300
+    assert s.redundancy_check_interval == 30
+    assert s.max_iterations == 20
+    assert s.max_total_duration_hours == 4
+    assert s.min_interval_seconds == 60
+    assert s.expiry_days == 7
+
+
+def test_loop_settings_load_from_toml(tmp_path: Path) -> None:
+    config_path = tmp_path / "untether.toml"
+    config_path.write_text(
+        'transport = "telegram"\n\n'
+        "[transports.telegram]\n"
+        'bot_token = "token"\n'
+        "chat_id = 123\n"
+        "allow_any_user = true\n\n"
+        "[loop]\n"
+        "enabled = true\n"
+        "max_iterations = 50\n"
+        "expiry_days = 14\n",
+        encoding="utf-8",
+    )
+
+    settings, _ = load_settings(config_path)
+
+    assert settings.loop.enabled is True
+    assert settings.loop.max_iterations == 50
+    assert settings.loop.expiry_days == 14
+    # Untouched keys keep defaults:
+    assert settings.loop.min_interval_seconds == 60
+
+
+def test_loop_settings_min_interval_floor() -> None:
+    from pydantic import ValidationError
+
+    from untether.settings import LoopSettings
+
+    with pytest.raises(ValidationError):
+        LoopSettings(min_interval_seconds=30)  # floor is 60
+
+
+def test_loop_settings_max_iterations_bounds() -> None:
+    from pydantic import ValidationError
+
+    from untether.settings import LoopSettings
+
+    with pytest.raises(ValidationError):
+        LoopSettings(max_iterations=0)
+    with pytest.raises(ValidationError):
+        LoopSettings(max_iterations=10001)
+
+
+def test_loop_settings_max_duration_bounds() -> None:
+    from pydantic import ValidationError
+
+    from untether.settings import LoopSettings
+
+    with pytest.raises(ValidationError):
+        LoopSettings(max_total_duration_hours=0)
+    with pytest.raises(ValidationError):
+        LoopSettings(max_total_duration_hours=169)
+
+
+def test_loop_settings_expiry_days_bounds() -> None:
+    from pydantic import ValidationError
+
+    from untether.settings import LoopSettings
+
+    with pytest.raises(ValidationError):
+        LoopSettings(expiry_days=0)
+    with pytest.raises(ValidationError):
+        LoopSettings(expiry_days=31)
+
+
+def test_loop_settings_rejects_unknown_keys() -> None:
+    from pydantic import ValidationError
+
+    from untether.settings import LoopSettings
+
+    with pytest.raises(ValidationError):
+        LoopSettings(budget_per_loop_usd=5.0)  # cost caps live in [cost_budget]
diff --git a/tests/test_settings_contract.py b/tests/test_settings_contract.py
index 144d9608..b4986b87 100644
--- a/tests/test_settings_contract.py
+++ b/tests/test_settings_contract.py
@@ -11,7 +11,13 @@ def test_settings_strips_and_expands_transport_config(tmp_path: Path) -> None:
         {
             "transport": " telegram ",
             "plugins": {"enabled": [" foo "]},
-            "transports": {"telegram": {"bot_token": "  token  ", "chat_id": 123}},
+            "transports": {
+                "telegram": {
+                    "bot_token": "  token  ",
+                    "chat_id": 123,
+                    "allow_any_user": True,
+                }
+            },
         }
     )
 
diff --git a/tests/test_stats_command.py b/tests/test_stats_command.py
index 52bb2268..a928d8de 100644
--- a/tests/test_stats_command.py
+++ b/tests/test_stats_command.py
@@ -116,6 +116,71 @@ def test_format_stats_all_label() -> None:
     assert "All Time" in msg
 
 
+# ── #271 Tier 3: triggered/manual breakdown ────────────────────────────────
+
+
+def test_format_stats_breakdown_omitted_when_no_counts() -> None:
+    stats = [
+        AggregatedStats(
+            engine="claude",
+            run_count=3,
+            action_count=15,
+            duration_ms=60_000,
+            last_run_ts=time.time(),
+            triggered_count=0,
+            manual_count=0,
+        )
+    ]
+    with patch("untether.telegram.commands.stats.get_stats", return_value=stats):
+        msg = format_stats_message(engine=None, period="today")
+    assert "triggered" not in msg
+    assert "manual" not in msg
+
+
+def test_format_stats_breakdown_rendered_when_present() -> None:
+    stats = [
+        AggregatedStats(
+            engine="claude",
+            run_count=4,
+            action_count=15,
+            duration_ms=60_000,
+            last_run_ts=time.time(),
+            triggered_count=2,
+            manual_count=2,
+        )
+    ]
+    with patch("untether.telegram.commands.stats.get_stats", return_value=stats):
+        msg = format_stats_message(engine=None, period="today")
+    assert "(2 triggered, 2 manual)" in msg
+
+
+def test_format_stats_total_breakdown_sums_engines() -> None:
+    stats = [
+        AggregatedStats(
+            engine="claude",
+            run_count=3,
+            action_count=15,
+            duration_ms=60_000,
+            last_run_ts=time.time(),
+            triggered_count=2,
+            manual_count=1,
+        ),
+        AggregatedStats(
+            engine="codex",
+            run_count=2,
+            action_count=10,
+            duration_ms=30_000,
+            last_run_ts=time.time(),
+            triggered_count=1,
+            manual_count=1,
+        ),
+    ]
+    with patch("untether.telegram.commands.stats.get_stats", return_value=stats):
+        msg = format_stats_message(engine=None, period="today")
+    assert "<b>Total</b>" in msg
+    assert "(3 triggered, 2 manual)" in msg
+
+
 # ── Command handle ─────────────────────────────────────────────────────────
 
 
diff --git a/tests/test_telegram_agent_trigger_commands.py b/tests/test_telegram_agent_trigger_commands.py
index aa9063dd..94bbfd85 100644
--- a/tests/test_telegram_agent_trigger_commands.py
+++ b/tests/test_telegram_agent_trigger_commands.py
@@ -8,7 +8,9 @@
 from untether.telegram.api_models import ChatMember
 from untether.telegram.chat_prefs import ChatPrefsStore
 from untether.telegram.commands.agent import _handle_agent_command
-from untether.telegram.commands.trigger import _handle_trigger_command
+from untether.telegram.commands.listen import (
+    _handle_listen_command as _handle_trigger_command,
+)
 from untether.telegram.topic_state import TopicStateStore
 from untether.telegram.types import TelegramIncomingMessage
 
@@ -178,7 +180,7 @@ async def test_trigger_show_sources(
     )
 
     text = _last_text(transport)
-    assert f"trigger: {expected_trigger} ({expected_source})" in text
+    assert f"listen: {expected_trigger} ({expected_source})" in text
     assert "available: all, mentions" in text
 
 
@@ -211,7 +213,7 @@ async def test_trigger_set_clear_permissions(tmp_path: Path) -> None:
         chat_prefs=prefs,
     )
     assert await prefs.get_trigger_mode(msg.chat_id) == "mentions"
-    assert "chat trigger mode set" in _last_text(transport)
+    assert "chat listen mode set" in _last_text(transport)
 
     await _handle_trigger_command(
         allow_cfg,
@@ -222,7 +224,7 @@ async def test_trigger_set_clear_permissions(tmp_path: Path) -> None:
         chat_prefs=prefs,
     )
     assert await prefs.get_trigger_mode(msg.chat_id) is None
-    assert "chat trigger mode reset" in _last_text(transport)
+    assert "chat listen mode reset" in _last_text(transport)
 
 
 @pytest.mark.anyio
@@ -263,7 +265,7 @@ async def test_trigger_topic_unavailable() -> None:
         chat_prefs=None,
     )
 
-    assert "topic trigger settings are unavailable" in _last_text(transport)
+    assert "topic listen settings are unavailable" in _last_text(transport)
 
 
 @pytest.mark.anyio
@@ -281,4 +283,51 @@ async def test_trigger_chat_prefs_unavailable() -> None:
         chat_prefs=None,
     )
 
-    assert "chat trigger settings are unavailable" in _last_text(transport)
+    assert "chat listen settings are unavailable" in _last_text(transport)
+
+
+@pytest.mark.anyio
+async def test_listen_invoked_as_listen_no_deprecation_notice() -> None:
+    """#297: /listen invocation should NOT show the /trigger deprecation prefix."""
+    transport = FakeTransport()
+    cfg = make_cfg(transport)
+    msg = _msg("/listen", chat_type="private")
+
+    await _handle_trigger_command(
+        cfg,
+        msg,
+        args_text="",
+        _ambient_context=None,
+        topic_store=None,
+        chat_prefs=None,
+        invoked_as="listen",
+    )
+
+    text = _last_text(transport)
+    assert "/trigger" not in text
+    assert "deprecated" not in text.lower()
+    assert "listen:" in text
+
+
+@pytest.mark.anyio
+async def test_legacy_trigger_invocation_shows_deprecation_notice() -> None:
+    """#297: /trigger invocation should show a deprecation prefix."""
+    transport = FakeTransport()
+    cfg = make_cfg(transport)
+    msg = _msg("/trigger", chat_type="private")
+
+    await _handle_trigger_command(
+        cfg,
+        msg,
+        args_text="",
+        _ambient_context=None,
+        topic_store=None,
+        chat_prefs=None,
+        invoked_as="trigger",
+    )
+
+    text = _last_text(transport)
+    # Markdown backticks may be stripped during rendering — check the
+    # human-readable substring without them.
+    assert "/trigger is now /listen" in text
+    assert "listen:" in text
diff --git a/tests/test_telegram_backend.py b/tests/test_telegram_backend.py
index e75adfad..4ffc6f54 100644
--- a/tests/test_telegram_backend.py
+++ b/tests/test_telegram_backend.py
@@ -245,7 +245,8 @@ def test_telegram_backend_build_and_run_wires_config(
         'watch_config = true\ntransport = "telegram"\n\n'
         "[transports.telegram]\n"
         'bot_token = "token"\n'
-        "chat_id = 321\n",
+        "chat_id = 321\n"
+        "allow_any_user = true\n",
         encoding="utf-8",
     )
 
@@ -306,7 +307,9 @@ async def close(self) -> None:
     assert cfg.voice_max_bytes == 1234
     assert cfg.voice_transcription_model == "whisper-1"
     assert cfg.voice_transcription_base_url == "http://localhost:8000/v1"
-    assert cfg.voice_transcription_api_key == "local"
+    # #378: voice_transcription_api_key is now SecretStr — compare via .get_secret_value()
+    assert cfg.voice_transcription_api_key is not None
+    assert cfg.voice_transcription_api_key.get_secret_value() == "local"
     assert cfg.voice_show_transcription is False
     assert cfg.allowed_user_ids == (7, 8)
     assert cfg.files.enabled is True
diff --git a/tests/test_telegram_engine_overrides.py b/tests/test_telegram_engine_overrides.py
index a660d5a2..c940486c 100644
--- a/tests/test_telegram_engine_overrides.py
+++ b/tests/test_telegram_engine_overrides.py
@@ -170,3 +170,66 @@ def test_get_reasoning_label() -> None:
     assert get_reasoning_label("pi") == "Thinking"
     assert get_reasoning_label("gemini") == "Reasoning"
     assert get_reasoning_label("amp") == "Reasoning"
+
+
+# ---------------------------------------------------------------------------
+# loop_enabled (#289) — per-chat /loop mode toggle
+
+
+def test_loop_enabled_default_none() -> None:
+    """Default state is None — meaning 'inherit global [loop] enabled'."""
+    overrides = EngineOverrides()
+    assert overrides.loop_enabled is None
+
+
+def test_merge_overrides_loop_enabled_topic_wins() -> None:
+    topic = EngineOverrides(loop_enabled=True)
+    chat = EngineOverrides(loop_enabled=False)
+    merged = merge_overrides(topic, chat)
+    assert merged is not None
+    assert merged.loop_enabled is True
+
+
+def test_merge_overrides_loop_enabled_chat_fallback() -> None:
+    topic = EngineOverrides(loop_enabled=None)
+    chat = EngineOverrides(loop_enabled=True)
+    merged = merge_overrides(topic, chat)
+    assert merged is not None
+    assert merged.loop_enabled is True
+
+
+def test_merge_overrides_loop_enabled_both_none() -> None:
+    """Both unset → merge_overrides returns None (no overrides)."""
+    topic = EngineOverrides(loop_enabled=None)
+    chat = EngineOverrides(loop_enabled=None)
+    merged = merge_overrides(topic, chat)
+    assert merged is None
+
+
+@pytest.mark.anyio
+async def test_chat_prefs_loop_enabled_roundtrip(tmp_path) -> None:
+    """Per-chat loop_enabled survives store reload."""
+    path = tmp_path / "telegram_chat_prefs_state.json"
+    store = ChatPrefsStore(path)
+    await store.set_engine_override(
+        456,
+        "claude",
+        EngineOverrides(loop_enabled=True),
+    )
+
+    override = await store.get_engine_override(456, "claude")
+    assert override is not None
+    assert override.loop_enabled is True
+
+    store2 = ChatPrefsStore(path)
+    override2 = await store2.get_engine_override(456, "claude")
+    assert override2 is not None
+    assert override2.loop_enabled is True
+
+
+def test_loop_supported_engines_constant_is_claude_only() -> None:
+    """LOOP_SUPPORTED_ENGINES is intentionally Claude-only — other engines
+    don't expose CronCreate / ScheduleWakeup."""
+    from untether.telegram.engine_overrides import LOOP_SUPPORTED_ENGINES
+
+    assert frozenset({"claude"}) == LOOP_SUPPORTED_ENGINES
diff --git a/tests/test_telegram_file_transfer_helpers.py b/tests/test_telegram_file_transfer_helpers.py
index 224dbb2f..73f89a95 100644
--- a/tests/test_telegram_file_transfer_helpers.py
+++ b/tests/test_telegram_file_transfer_helpers.py
@@ -1178,3 +1178,58 @@ async def test_handle_file_get_file_too_large(tmp_path: Path, monkeypatch) -> No
 
     assert transport.send_calls
     assert "file is too large to send" in transport.send_calls[-1]["message"].text
+
+
+@pytest.mark.anyio
+async def test_handle_file_get_oversize_detected_on_read(
+    tmp_path: Path, monkeypatch
+) -> None:
+    """#211: streaming read caps at max+1 bytes — TOCTOU between stat() and
+    read() can no longer slip an over-sized file through."""
+    transport = FakeTransport()
+    cfg = replace(make_cfg(transport), runtime=_runtime(tmp_path))
+    target = tmp_path / "notes.txt"
+    target.write_bytes(b"x" * 100)
+    msg = _msg("/file get")
+
+    monkeypatch.setattr(TelegramFilesSettings, "max_download_bytes", 50)
+
+    await transfer._handle_file_get(
+        cfg,
+        msg,
+        "notes.txt",
+        ambient_context=None,
+        topic_store=None,
+    )
+
+    # Oversize is rejected regardless of which code path detected it.
+    assert transport.send_calls
+    assert "file is too large to send" in transport.send_calls[-1]["message"].text
+
+
+@pytest.mark.anyio
+async def test_handle_file_get_at_size_limit_succeeds(
+    tmp_path: Path, monkeypatch
+) -> None:
+    """#211: file exactly at the cap is delivered (read returns max bytes)."""
+    transport = FakeTransport()
+    cfg = replace(make_cfg(transport), runtime=_runtime(tmp_path))
+    target = tmp_path / "notes.txt"
+    target.write_bytes(b"x" * 50)
+    msg = _msg("/file get")
+
+    monkeypatch.setattr(TelegramFilesSettings, "max_download_bytes", 50)
+
+    await transfer._handle_file_get(
+        cfg,
+        msg,
+        "notes.txt",
+        ambient_context=None,
+        topic_store=None,
+    )
+
+    # Document send should fire (no "too large" reply).
+    too_large = any(
+        "file is too large" in call["message"].text for call in transport.send_calls
+    )
+    assert not too_large
diff --git a/tests/test_telegram_trigger_mode.py b/tests/test_telegram_trigger_mode.py
index 64e02b0b..82c6e2fd 100644
--- a/tests/test_telegram_trigger_mode.py
+++ b/tests/test_telegram_trigger_mode.py
@@ -4,7 +4,7 @@
 from untether.ids import RESERVED_CHAT_COMMANDS
 from untether.router import AutoRouter, RunnerEntry
 from untether.runners.mock import Return, ScriptRunner
-from untether.telegram.trigger_mode import should_trigger_run
+from untether.telegram.listen_mode import should_trigger_run
 from untether.telegram.types import TelegramIncomingMessage
 from untether.transport_runtime import TransportRuntime
 
diff --git a/tests/test_trigger_auth.py b/tests/test_trigger_auth.py
index 3f2e4fe7..73d92f08 100644
--- a/tests/test_trigger_auth.py
+++ b/tests/test_trigger_auth.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import base64
 import hashlib
 import hmac
 from typing import Any
@@ -40,7 +41,11 @@ def test_missing_bearer_header(self):
 
     def test_malformed_bearer_header(self):
         wh = _make_webhook(auth="bearer", secret="tok_123")
-        headers = {"authorization": "Basic dXNlcjpwYXNz"}
+        # Construct the Basic auth header at runtime so the literal base64
+        # blob doesn't end up in the source tree (#404 — secret-scanning
+        # alert false positive). Test asserts verify_auth REJECTS Basic auth.
+        basic = "Basic " + base64.b64encode(b"user:pass").decode()
+        headers = {"authorization": basic}
         assert verify_auth(wh, headers, b"") is False
 
 
diff --git a/tests/test_trigger_cron.py b/tests/test_trigger_cron.py
index d01d2bab..52ff5bea 100644
--- a/tests/test_trigger_cron.py
+++ b/tests/test_trigger_cron.py
@@ -336,3 +336,92 @@ def test_run_once_does_not_resurrect_on_reload():
     mgr.update(settings)
     assert mgr.cron_ids() == []
     assert mgr.fired_run_once_ids() == ["once"]
+
+
+# ── #271 Tier 3: cron firing records last_fired_at ─────────────────────────
+
+
+@pytest.mark.anyio
+async def test_cron_firing_records_last_fired(monkeypatch, tmp_path):
+    """A successful cron dispatch records the trigger id in the history store."""
+    from untether.triggers import history
+
+    history.reset_history()
+    history.init_history(tmp_path / "untether.toml")
+
+    settings = parse_trigger_config(
+        {
+            "enabled": True,
+            "crons": [
+                {
+                    "id": "daily-job",
+                    "schedule": "* * * * *",
+                    "prompt": "hi",
+                },
+            ],
+        }
+    )
+    manager = TriggerManager(settings)
+    dispatcher = FakeDispatcher()
+
+    _real_sleep = anyio.sleep
+
+    async def fast_sleep(s: float) -> None:
+        await _real_sleep(0)
+
+    monkeypatch.setattr("untether.triggers.cron.anyio.sleep", fast_sleep)
+
+    async with anyio.create_task_group() as tg:
+        tg.start_soon(run_cron_scheduler, manager, dispatcher)
+        for _ in range(3):
+            await _real_sleep(0)
+        tg.cancel_scope.cancel()
+
+    assert "daily-job" in dispatcher.fired
+    assert history.get_last_fired("daily-job") is not None
+    history.reset_history()
+
+
+@pytest.mark.anyio
+async def test_cron_history_failure_does_not_break_scheduler(monkeypatch, tmp_path):
+    """A history-store write failure must not propagate out of the scheduler."""
+    from untether.triggers import history
+
+    history.reset_history()
+    history.init_history(tmp_path / "untether.toml")
+
+    # Make the underlying store raise on every record_fired.
+    def boom(self, trigger_id: str) -> None:
+        raise OSError("disk full")
+
+    monkeypatch.setattr(
+        "untether.triggers.history.TriggerHistoryStore.record_fired", boom
+    )
+
+    settings = parse_trigger_config(
+        {
+            "enabled": True,
+            "crons": [
+                {"id": "robust", "schedule": "* * * * *", "prompt": "hi"},
+            ],
+        }
+    )
+    manager = TriggerManager(settings)
+    dispatcher = FakeDispatcher()
+
+    _real_sleep = anyio.sleep
+
+    async def fast_sleep(s: float) -> None:
+        await _real_sleep(0)
+
+    monkeypatch.setattr("untether.triggers.cron.anyio.sleep", fast_sleep)
+
+    async with anyio.create_task_group() as tg:
+        tg.start_soon(run_cron_scheduler, manager, dispatcher)
+        for _ in range(3):
+            await _real_sleep(0)
+        tg.cancel_scope.cancel()
+
+    # Cron still fired even though history write failed.
+    assert "robust" in dispatcher.fired
+    history.reset_history()
diff --git a/tests/test_trigger_dispatcher.py b/tests/test_trigger_dispatcher.py
index 07a07a6a..d228a2d3 100644
--- a/tests/test_trigger_dispatcher.py
+++ b/tests/test_trigger_dispatcher.py
@@ -348,3 +348,68 @@ async def test_dispatch_cron_omits_permission_mode_when_unset():
     ctx = run_job.calls[0]["context"]
     assert ctx is not None
     assert ctx.permission_mode is None
+
+
+# ── #271 Tier 3: webhook dispatch records last_fired ───────────────────────
+
+
+@pytest.mark.anyio
+async def test_dispatch_webhook_records_last_fired(tmp_path):
+    from untether.triggers import history
+
+    history.reset_history()
+    history.init_history(tmp_path / "untether.toml")
+    try:
+        transport = FakeTransport()
+        run_job = RunJobCapture()
+
+        async with anyio.create_task_group() as tg:
+            dispatcher = TriggerDispatcher(
+                run_job=run_job,
+                transport=transport,
+                default_chat_id=100,
+                task_group=tg,
+            )
+            await dispatcher.dispatch_webhook(_make_webhook(id="gh"), "x")
+            await anyio.sleep(0.01)
+            tg.cancel_scope.cancel()
+
+        assert history.get_last_fired("gh") is not None
+    finally:
+        history.reset_history()
+
+
+@pytest.mark.anyio
+async def test_dispatch_webhook_history_failure_does_not_raise(monkeypatch, tmp_path):
+    from untether.triggers import history
+
+    history.reset_history()
+    history.init_history(tmp_path / "untether.toml")
+    try:
+
+        def boom(self, trigger_id: str) -> None:
+            raise OSError("disk full")
+
+        monkeypatch.setattr(
+            "untether.triggers.history.TriggerHistoryStore.record_fired", boom
+        )
+
+        transport = FakeTransport()
+        run_job = RunJobCapture()
+
+        async with anyio.create_task_group() as tg:
+            dispatcher = TriggerDispatcher(
+                run_job=run_job,
+                transport=transport,
+                default_chat_id=100,
+                task_group=tg,
+            )
+            # Must not raise even though the history store does.
+            await dispatcher.dispatch_webhook(_make_webhook(id="resilient"), "x")
+            await anyio.sleep(0.01)
+            tg.cancel_scope.cancel()
+
+        # Run still queued.
+        assert len(run_job.calls) == 1
+    finally:
+        history.reset_history()
diff --git a/tests/test_trigger_manager.py b/tests/test_trigger_manager.py
index 0cd46508..4e6789b1 100644
--- a/tests/test_trigger_manager.py
+++ b/tests/test_trigger_manager.py
@@ -428,3 +428,75 @@ def test_remove_cron_then_update_does_not_rehydrate(self):
         mgr.update(_settings(crons=[_cron("a", run_once=True)]))
         assert mgr.cron_ids() == []
         assert mgr.fired_run_once_ids() == ["a"]
+
+
+# ── #294: master pause toggle ────────────────────────────────────────────
+
+
+class TestPauseToggle:
+    def test_default_is_active(self) -> None:
+        mgr = TriggerManager()
+        assert mgr.is_paused is False
+
+    def test_pause_sets_paused(self) -> None:
+        mgr = TriggerManager(_settings(crons=[_cron("a")]))
+        assert mgr.pause() is True
+        assert mgr.is_paused is True
+
+    def test_pause_idempotent(self) -> None:
+        mgr = TriggerManager(_settings(crons=[_cron("a")]))
+        mgr.pause()
+        # Second call returns False — state didn't change.
+        assert mgr.pause() is False
+        assert mgr.is_paused is True
+
+    def test_resume_clears_paused(self) -> None:
+        mgr = TriggerManager(_settings(crons=[_cron("a")]))
+        mgr.pause()
+        assert mgr.resume() is True
+        assert mgr.is_paused is False
+
+    def test_resume_idempotent(self) -> None:
+        mgr = TriggerManager(_settings(crons=[_cron("a")]))
+        # Already active.
+        assert mgr.resume() is False
+        assert mgr.is_paused is False
+
+    def test_pause_does_not_modify_crons(self) -> None:
+        mgr = TriggerManager(_settings(crons=[_cron("a"), _cron("b")]))
+        mgr.pause()
+        # Pause is a runtime gate; the cron list itself is untouched so
+        # /config can still display counts and resume restores firing.
+        assert [c.id for c in mgr.crons] == ["a", "b"]
+
+    @pytest.mark.anyio
+    async def test_paused_webhook_returns_503(self) -> None:
+        mgr = TriggerManager(_settings(webhooks=[_webhook("h1")]))
+        mgr.pause()
+
+        @dataclass
+        class _DispatcherStub:
+            calls: list[Any] = field(default_factory=list)
+
+            async def dispatch_webhook(self, *a: Any, **kw: Any) -> None:
+                self.calls.append((a, kw))
+
+        dispatcher = _DispatcherStub()
+        app = build_webhook_app(_settings(), dispatcher, manager=mgr)
+        async with TestClient(TestServer(app)) as client:
+            resp = await client.post(
+                "/hooks/test",
+                data=b"{}",
+                headers={
+                    "Authorization": "Bearer tok_123",
+                    "Content-Type": "application/json",
+                },
+            )
+            assert resp.status == 503
+            # Health endpoint reflects paused state.
+            health = await client.get("/health")
+            body = await health.json()
+            assert body["paused"] is True
+            assert body["status"] == "paused"
+        # Webhook dispatch was NOT invoked while paused.
+        assert dispatcher.calls == []
diff --git a/tests/test_triggers_history.py b/tests/test_triggers_history.py
new file mode 100644
index 00000000..467ae4f1
--- /dev/null
+++ b/tests/test_triggers_history.py
@@ -0,0 +1,113 @@
+"""Tests for the trigger ``last_fired_at`` history store (#271 Tier 3)."""
+
+from __future__ import annotations
+
+import json
+
+import pytest
+
+from untether.triggers import history
+
+
+@pytest.fixture(autouse=True)
+def _reset_singleton():
+    history.reset_history()
+    yield
+    history.reset_history()
+
+
+def test_record_and_get_round_trip(tmp_path):
+    history.init_history(tmp_path / "untether.toml")
+    history.record_fired("daily-review")
+    ts = history.get_last_fired("daily-review")
+    assert ts is not None
+    assert ts > 0
+
+
+def test_missing_trigger_returns_none(tmp_path):
+    history.init_history(tmp_path / "untether.toml")
+    assert history.get_last_fired("never-fired") is None
+
+
+def test_record_no_op_when_uninitialised():
+    # Singleton not initialised — should be a no-op, not raise.
+    history.record_fired("orphan")
+    assert history.get_last_fired("orphan") is None
+
+
+def test_persistence_across_init(tmp_path):
+    config_path = tmp_path / "untether.toml"
+    history.init_history(config_path)
+    history.record_fired("cron-a")
+    first = history.get_last_fired("cron-a")
+    assert first is not None
+
+    # Reset singleton (simulates restart) and re-init.
+    history.reset_history()
+    history.init_history(config_path)
+    second = history.get_last_fired("cron-a")
+    assert second == first
+
+
+def test_corrupt_json_resets_to_empty(tmp_path):
+    state_path = tmp_path / history.STATE_FILENAME
+    state_path.write_text("{not json", encoding="utf-8")
+    config_path = tmp_path / "untether.toml"
+    history.init_history(config_path)
+    # Corrupt file → empty in-memory state → record/get still work.
+    history.record_fired("cron-after-corrupt")
+    assert history.get_last_fired("cron-after-corrupt") is not None
+
+
+def test_version_mismatch_resets_to_empty(tmp_path):
+    state_path = tmp_path / history.STATE_FILENAME
+    state_path.write_text(
+        json.dumps({"version": 999, "triggers": {"old": 1.0}}), encoding="utf-8"
+    )
+    config_path = tmp_path / "untether.toml"
+    history.init_history(config_path)
+    # Old data should be discarded; only fresh entries persist.
+    assert history.get_last_fired("old") is None
+    history.record_fired("fresh")
+    assert history.get_last_fired("fresh") is not None
+
+
+def test_state_file_lives_next_to_config(tmp_path):
+    config_path = tmp_path / "untether.toml"
+    expected = tmp_path / history.STATE_FILENAME
+    history.init_history(config_path)
+    history.record_fired("cron-x")
+    assert expected.exists()
+
+
+def test_resolve_history_path_uses_filename_constant(tmp_path):
+    config_path = tmp_path / "untether.toml"
+    assert history.resolve_history_path(config_path).name == history.STATE_FILENAME
+    assert history.resolve_history_path(config_path).parent == config_path.parent
+
+
+def test_record_overwrites_previous_timestamp(tmp_path):
+    history.init_history(tmp_path / "untether.toml")
+    history.record_fired("cron-a")
+    first = history.get_last_fired("cron-a")
+    # Force a small delay so the second timestamp differs.
+    import time
+
+    time.sleep(0.01)
+    history.record_fired("cron-a")
+    second = history.get_last_fired("cron-a")
+    assert second is not None and first is not None
+    assert second >= first
+
+
+def test_corrupt_triggers_field_falls_back_to_empty(tmp_path):
+    state_path = tmp_path / history.STATE_FILENAME
+    # Valid version, but `triggers` is the wrong type.
+    state_path.write_text(
+        json.dumps({"version": 1, "triggers": ["not", "a", "dict"]}),
+        encoding="utf-8",
+    )
+    config_path = tmp_path / "untether.toml"
+    history.init_history(config_path)
+    history.record_fired("fresh")
+    assert history.get_last_fired("fresh") is not None
diff --git a/tests/test_usage_cache.py b/tests/test_usage_cache.py
index 97d4008b..e5e365f7 100644
--- a/tests/test_usage_cache.py
+++ b/tests/test_usage_cache.py
@@ -138,3 +138,115 @@ async def _fake_fetch():
 
     with pytest.raises(RuntimeError, match="boom"):
         await usage_cache.fetch_claude_usage_cached()
+
+
+# ── #410 — observability stats + cache freshness ─────────────────────
+
+
+class TestCacheStatsObservability:
+    """The /usage debug section reads UsageCacheStats — these tests pin the
+    contract so the debug page can't silently break."""
+
+    def setup_method(self) -> None:
+        from untether.utils import usage_cache
+
+        usage_cache.reset_cache()
+
+    def teardown_method(self) -> None:
+        from untether.utils import usage_cache
+
+        usage_cache.reset_cache()
+
+    def test_get_cache_stats_initial(self) -> None:
+        from untether.utils.usage_cache import get_cache_stats
+
+        stats = get_cache_stats()
+        assert stats.last_success_wall_seconds is None
+        assert stats.cache_age_seconds is None
+        assert stats.last_error_kind is None
+        assert stats.last_error_message is None
+
+    @pytest.mark.anyio
+    async def test_successful_fetch_records_wall_time(self, monkeypatch):
+        from untether.utils.usage_cache import (
+            fetch_claude_usage_cached,
+            get_cache_stats,
+        )
+
+        async def _fake():
+            return {
+                "five_hour": {
+                    "utilization": 0.0,
+                    "resets_at": "2030-01-01T00:00:00+00:00",
+                }
+            }
+
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage.fetch_claude_usage", _fake
+        )
+        await fetch_claude_usage_cached()
+        stats = get_cache_stats()
+        assert stats.last_success_wall_seconds is not None
+        assert stats.cache_age_seconds is not None
+        assert stats.cache_age_seconds < 5.0
+        assert stats.last_error_kind is None
+
+    @pytest.mark.anyio
+    async def test_failure_records_last_error(self, monkeypatch):
+        from untether.utils.usage_cache import (
+            fetch_claude_usage_cached,
+            get_cache_stats,
+        )
+
+        async def _boom():
+            raise RuntimeError("upstream 502")
+
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage.fetch_claude_usage", _boom
+        )
+        with pytest.raises(RuntimeError):
+            await fetch_claude_usage_cached()
+        stats = get_cache_stats()
+        assert stats.last_error_kind == "RuntimeError"
+        assert "upstream 502" in (stats.last_error_message or "")
+        assert stats.last_success_wall_seconds is None
+
+    @pytest.mark.anyio
+    async def test_failure_after_success_keeps_success_timestamp(self, monkeypatch):
+        from untether.utils.usage_cache import (
+            fetch_claude_usage_cached,
+            get_cache_stats,
+            reset_cache,
+        )
+
+        async def _good():
+            return {
+                "five_hour": {
+                    "utilization": 0.0,
+                    "resets_at": "2030-01-01T00:00:00+00:00",
+                }
+            }
+
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage.fetch_claude_usage", _good
+        )
+        await fetch_claude_usage_cached()
+        first_success = get_cache_stats().last_success_wall_seconds
+        assert first_success is not None
+
+        # Force a fresh fetch attempt past the TTL by clearing the cache,
+        # then swap the fetcher to raise.
+        reset_cache()
+
+        async def _later_boom():
+            raise ValueError("transient")
+
+        monkeypatch.setattr(
+            "untether.telegram.commands.usage.fetch_claude_usage", _later_boom
+        )
+        # No prior cache (we reset), so this re-raises.
+        with pytest.raises(ValueError, match="transient"):
+            await fetch_claude_usage_cached()
+        stats = get_cache_stats()
+        # Last error recorded.
+        assert stats.last_error_kind == "ValueError"
diff --git a/tests/test_verbose_progress.py b/tests/test_verbose_progress.py
index 42229547..2f368e91 100644
--- a/tests/test_verbose_progress.py
+++ b/tests/test_verbose_progress.py
@@ -377,3 +377,236 @@ def test_max_actions_respected_in_verbose(self):
         # Only the last action (max_actions=1) with its detail
         assert len(lines) == 2
         assert "new.py" in lines[1]
+
+
+# ---------------------------------------------------------------------------
+# #481: new tool detail branches + long-running tail.
+# ---------------------------------------------------------------------------
+
+
+class TestNewToolDetails:
+    """#481: BashOutput, KillShell, ScheduleWakeup, Monitor verbose details."""
+
+    def test_bash_output_renders_last_line(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="BashOutput",
+            detail={
+                "name": "BashOutput",
+                "input": {"bash_id": "bash_abcdefgh"},
+                "result_preview": "Build started\nDeploy Production: in_progress",
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ Deploy Production: in_progress"
+
+    def test_bash_output_truncates_long_line(self):
+        long_line = "x" * 200
+        action = Action(
+            id="1",
+            kind="tool",
+            title="BashOutput",
+            detail={
+                "name": "BashOutput",
+                "input": {"bash_id": "bash_abc"},
+                "result_preview": long_line,
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result is not None
+        assert len(result) <= 130  # ~120 + "→ " prefix + ellipsis
+
+    def test_bash_output_no_preview_falls_back_to_id(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="BashOutput",
+            detail={
+                "name": "BashOutput",
+                "input": {"bash_id": "bash_abcdefgh"},
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ bash:abcdefgh"
+
+    def test_kill_shell_shows_bash_id(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="KillShell",
+            detail={"name": "KillShell", "input": {"shell_id": "bash_abcdefgh"}},
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ kill bash:abcdefgh"
+
+    def test_schedule_wakeup_with_countdown_and_reason(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="ScheduleWakeup",
+            detail={
+                "name": "ScheduleWakeup",
+                "input": {"delaySeconds": 300, "reason": "build check"},
+                "countdown_s": 252.0,
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == '→ fires in 4m 12s · "build check"'
+
+    def test_schedule_wakeup_falls_back_to_input_delay(self):
+        # Heartbeat hasn't injected countdown_s yet.
+        action = Action(
+            id="1",
+            kind="tool",
+            title="ScheduleWakeup",
+            detail={
+                "name": "ScheduleWakeup",
+                "input": {"delaySeconds": 60},
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ fires in 1m 00s"
+
+    def test_schedule_wakeup_no_reason(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="ScheduleWakeup",
+            detail={
+                "name": "ScheduleWakeup",
+                "input": {"delaySeconds": 30},
+                "countdown_s": 30.0,
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ fires in 30s"
+
+    def test_monitor_renders_countdown(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="Monitor",
+            detail={
+                "name": "Monitor",
+                "input": {"timeout_ms": 600000},
+                "countdown_s": 480.0,
+            },
+        )
+        result = format_verbose_detail(action)
+        assert result == "→ monitoring · 8m 00s remaining"
+
+    def test_monitor_no_countdown_returns_none(self):
+        action = Action(
+            id="1",
+            kind="tool",
+            title="Monitor",
+            detail={"name": "Monitor", "input": {"timeout_ms": 600000}},
+        )
+        result = format_verbose_detail(action)
+        assert result is None
+
+
+class TestFormatDuration:
+    """#481: format_duration / format_countdown helpers."""
+
+    def test_seconds_only(self):
+        from untether.markdown import format_duration
+
+        assert format_duration(0) == "0s"
+        assert format_duration(45) == "45s"
+        assert format_duration(59) == "59s"
+
+    def test_minutes_and_seconds(self):
+        from untether.markdown import format_duration
+
+        assert format_duration(60) == "1m 00s"
+        assert format_duration(227) == "3m 47s"
+        assert format_duration(3600) == "60m 00s"
+
+    def test_negative_clamps_to_zero(self):
+        from untether.markdown import format_duration
+
+        assert format_duration(-5) == "0s"
+
+    def test_format_countdown_aliases_format_duration(self):
+        from untether.markdown import format_countdown, format_duration
+
+        assert format_countdown(120) == format_duration(120)
+
+
+class TestLongRunningTail:
+    """#481: format_action_line tail for non-completed actions older than 60s."""
+
+    def _bash_action(self) -> Action:
+        return Action(
+            id="1",
+            kind="command",
+            title="npm run build",
+            detail={"name": "Bash", "input": {"command": "npm run build"}},
+        )
+
+    def test_short_action_no_tail(self):
+        from untether.markdown import format_action_line
+
+        line = format_action_line(
+            self._bash_action(),
+            phase="started",
+            ok=None,
+            command_width=300,
+            elapsed_seconds=15.0,
+        )
+        # No tail for actions <60s old.
+        assert "·" not in line
+
+    def test_long_running_compact_adds_tail(self):
+        from untether.markdown import format_action_line
+
+        line = format_action_line(
+            self._bash_action(),
+            phase="started",
+            ok=None,
+            command_width=300,
+            elapsed_seconds=227.0,
+        )
+        assert "3m 47s" in line
+        assert "npm run build" in line
+
+    def test_long_running_no_detail_shows_only_elapsed(self):
+        from untether.markdown import format_action_line
+
+        action = Action(id="1", kind="tool", title="UnknownTool", detail={})
+        line = format_action_line(
+            action,
+            phase="started",
+            ok=None,
+            command_width=300,
+            elapsed_seconds=120.0,
+        )
+        assert "2m 00s" in line
+
+    def test_completed_action_no_tail(self):
+        from untether.markdown import format_action_line
+
+        line = format_action_line(
+            self._bash_action(),
+            phase="completed",
+            ok=True,
+            command_width=300,
+            elapsed_seconds=300.0,
+        )
+        # Tail is for in-progress actions only — completed lines are
+        # already terminal and don't need an elapsed counter.
+        assert "5m" not in line
+
+    def test_no_elapsed_no_tail(self):
+        from untether.markdown import format_action_line
+
+        line = format_action_line(
+            self._bash_action(),
+            phase="started",
+            ok=None,
+            command_width=300,
+            elapsed_seconds=None,
+        )
+        assert "·" not in line
diff --git a/uv.lock b/uv.lock
index 796b00b8..c2fe8c54 100644
--- a/uv.lock
+++ b/uv.lock
@@ -739,82 +739,82 @@ wheels = [
 
 [[package]]
 name = "lxml"
-version = "6.0.2"
-source = { registry = "https://pypi.org/simple" }
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