Coding-Autopilot-System · OgeonX-Ai · Jun 5, 2026 · May 21, 2026 · May 21, 2026 · May 21, 2026
diff --git a/.planning/MILESTONES.md b/.planning/MILESTONES.md
@@ -0,0 +1,48 @@
+# Milestones — Enterprise GitHub Portfolio + gsd-orchestrator
+
+## v1.0 — Portfolio Launch (COMPLETE 2026-05-25)
+
+**Goal:** Transform Coding-Autopilot-System into a job-landing enterprise portfolio.
+
+**Phases:** 1-6 (23 requirements)
+
+**What shipped:**
+- All 3 flagship repos (gsd-orchestrator, Promptimprover, autogen) have enterprise READMEs, CI badges, Mermaid diagrams, and GitHub Wikis
+- gsd-orchestrator v1.0.0 release with feature-narrative notes
+- Coding-Autopilot-System org profile with system diagram
+- OgeonX-Ai personal profile linking to org
+- MIT LICENSE on all repos
+- GitHub topics, descriptions, cross-repo links
+
+---
+
+## v2.0 — Full Org Documentation (COMPLETE 2026-05-28)
+
+**Goal:** Every public repo in both orgs reaches Level A documentation standard.
+
+**Phases:** 7-11 (11 requirements)
+
+**What shipped:**
+- ci-autopilot: emergency fix (1,956 runner-offline issues bulk-closed, cron disabled), Level A docs
+- autopilot-core, autopilot-demo: Level A docs (README, CI, wiki, topics)
+- cloud-security-service-model: enterprise README rewrite, wiki, CI green (markdownlint fix)
+- enterprise-ai-gateway, android: AI engineer reframe, Level A docs
+- kim-ai-voice-demo, My-CV: AI portfolio framing, Level A docs
+- Topics audit: all 11 repos have 5-10 accurate topics
+- Issue templates: bug_report.md + feature_request.md in 3 flagship CAS repos
+- One manual step outstanding: org owner pins gsd-orchestrator, Promptimprover, autogen
+
+---
+
+## v3.0 — gsd-orchestrator Feature Expansion (ACTIVE)
+
+**Goal:** Extend gsd-orchestrator from a single-repo issue-to-PR automator into a multi-repo, triage-aware, test-generating autonomous engineering platform.
+
+**Phases:** 12-16 (in progress)
+
+**Target features:**
+- Robustness foundation (structured logging, unit tests, circuit breaker)
+- Smarter issue triage (TriagingState, label classification, --triage mode)
+- Autonomous test generation (TestGeneratingState, xUnit, committed to branch)
+- PR review loop (--pr mode, structured code review, approve/request-changes)
+- Multi-repo support (GSD_REPOS config, watch across repos, per-repo checkpointing)
diff --git a/.planning/PROJECT.md b/.planning/PROJECT.md
@@ -1,4 +1,17 @@
-# Enterprise GitHub Portfolio
+# Enterprise GitHub Portfolio + gsd-orchestrator
+
+## Current Milestone: v3.0 — gsd-orchestrator Feature Expansion
+
+**Goal:** Extend gsd-orchestrator from a single-repo issue-to-PR automator into a multi-repo, triage-aware, test-generating autonomous engineering platform.
+
+**Target features:**
+- Robustness foundation (Serilog, xUnit, circuit breaker)
+- Smarter issue triage (TriagingState, --triage mode, duplicate detection)
+- Autonomous test generation (TestGeneratingState, xUnit tests on branch)
+- PR review loop (--pr mode, structured inline comments, approve/request-changes)
+- Multi-repo support (GSD_REPOS config, per-repo checkpointing)
+
+---
 
 ## What This Is
 
@@ -69,16 +82,17 @@ A hiring manager should be able to spend 5 minutes on the GitHub org and immedia
 
 - [ ] All repos have correct GitHub topics for discoverability
 - [ ] Org .github profile README showcases all three projects as a system
-- [ ] gsd-orchestrator has GitHub Actions CI (.NET build)
-- [ ] gsd-orchestrator has Mermaid architecture diagram in README
-- [ ] gsd-orchestrator has GitHub Wiki (4+ pages)
-- [ ] gsd-orchestrator has v1.0.0 release
-- [ ] Promptimprover has updated README and GitHub Actions CI
-- [ ] Promptimprover has GitHub Wiki
-- [ ] autogen has updated README and GitHub Actions CI
-- [ ] autogen has GitHub Wiki
+- [x] gsd-orchestrator has GitHub Actions CI (.NET build) — Validated in Phase 2: CI green, badge live
+- [x] gsd-orchestrator has Mermaid architecture diagram in README — Validated in Phase 2: stateDiagram-v2 + flowchart LR
+- [x] gsd-orchestrator has GitHub Wiki (4+ pages) — Validated in Phase 3: Home, Setup Guide, Architecture, Configuration Reference live
+- [x] gsd-orchestrator has v1.0.0 release — Validated in Phase 3: feature-narrative release notes, not draft/pre-release
+- [x] Promptimprover has updated README and GitHub Actions CI — Validated in Phase 4: hero line, badges, Mermaid diagram, CI green
+- [x] Promptimprover has GitHub Wiki — Validated in Phase 4: Home, Setup Guide, Architecture, Configuration Reference live
+- [x] autogen has updated README and GitHub Actions CI — Validated in Phase 5: enterprise hero line, CI green (Python 3.12)
+- [x] autogen has GitHub Wiki — Validated in Phase 5: Home, Setup Guide, Architecture, Configuration Reference live
 - [ ] Personal OgeonX-Ai profile README links to org and highlights top projects
-- [ ] All READMEs have CI/version badges
+- [x] gsd-orchestrator README has CI / .NET 10 / License badges — Validated in Phase 2
+- [x] Promptimprover and autogen READMEs have CI/version badges — Validated in Phases 4 and 5
 
 ### Out of Scope
 
@@ -100,4 +114,4 @@ This document evolves at phase transitions and milestone boundaries.
 2. Core Value check — still the right priority?
 
 ---
-*Last updated: 2026-05-21 after initialization*
+*Last updated: 2026-06-05 — MILESTONE 3.0 COMPLETE. Phase 16 (Multi-Repo Support): GSD_REPOS JSON array replaces single owner/repo env vars (backwards compat); watch mode loops all repos with per-repo rate-limit delay; checkpoints namespaced {owner}_{repo}_{workflowId}.json; IdleState DI cleaned up. 35 tests green. All 5 phases (12–16) and 13 v3 requirements satisfied.*
diff --git a/.planning/REQUIREMENTS.md b/.planning/REQUIREMENTS.md
@@ -12,39 +12,103 @@
 
 ### gsd-orchestrator (GSD)
 
-- [ ] **GSD-01**: GitHub Actions CI workflow (.NET 10 build) with passing badge in README
-- [ ] **GSD-02**: Mermaid state machine diagram in README (full workflow: Idle→Done)
-- [ ] **GSD-03**: Mermaid component diagram in README (orchestrator ↔ MCP server ↔ Claude)
-- [ ] **GSD-04**: GitHub Wiki — Home page with overview and navigation
-- [ ] **GSD-05**: GitHub Wiki — Setup Guide (prerequisites, clone, .env, first run)
-- [ ] **GSD-06**: GitHub Wiki — Architecture deep-dive (state machine, components, data flow)
-- [ ] **GSD-07**: GitHub Wiki — Configuration Reference (all env vars)
-- [ ] **GSD-08**: GitHub Release v1.0.0 with changelog
-- [ ] **GSD-09**: README badges: CI, .NET 10, License
+- [x] **GSD-01**: GitHub Actions CI workflow (.NET 10 build) with passing badge in README — Phase 2 ✓
+- [x] **GSD-02**: Mermaid state machine diagram in README (full workflow: Idle→Done) — Phase 2 ✓
+- [x] **GSD-03**: Mermaid component diagram in README (orchestrator ↔ MCP server ↔ Claude) — Phase 2 ✓
+- [x] **GSD-04**: GitHub Wiki — Home page with overview and navigation — Phase 3 (03-01) ✓
+- [x] **GSD-05**: GitHub Wiki — Setup Guide (prerequisites, clone, .env, first run) — Phase 3 (03-01) ✓
+- [x] **GSD-06**: GitHub Wiki — Architecture deep-dive (state machine, components, data flow) — Phase 3 (03-01) ✓
+- [x] **GSD-07**: GitHub Wiki — Configuration Reference (all env vars) — Phase 3 (03-01) ✓
+- [x] **GSD-08**: GitHub Release v1.0.0 with feature-narrative release notes — Phase 3 (03-02) ✓
+- [x] **GSD-09**: README badges: CI, .NET 10, License — Phase 2 ✓
 
 ### Promptimprover (PI)
 
-- [ ] **PI-01**: README rewritten — remove internal language, add hero line, architecture section
-- [ ] **PI-02**: GitHub Actions CI workflow (TypeScript/Node build) with passing badge
-- [ ] **PI-03**: GitHub Wiki — Home, Setup Guide, Architecture, Configuration Reference
-- [ ] **PI-04**: README badges: CI, Node, License
-- [ ] **PI-05**: Cross-repo links to org and sibling projects
+- [x] **PI-01**: README rewritten — remove internal language, add hero line, architecture section — Phase 4 ✓
+- [x] **PI-02**: GitHub Actions CI workflow (TypeScript/Node build) with passing badge — Phase 4 ✓
+- [x] **PI-03**: GitHub Wiki — Home, Setup Guide, Architecture, Configuration Reference — Phase 4 ✓
+- [x] **PI-04**: README badges: CI, Node, License — Phase 4 ✓
+- [x] **PI-05**: Cross-repo links to org and sibling projects — Phase 4 ✓
 
 ### autogen (AG)
 
-- [ ] **AG-01**: README rewritten — remove "starter kit" framing, add enterprise positioning
-- [ ] **AG-02**: GitHub Actions CI workflow (Python build) with passing badge
-- [ ] **AG-03**: GitHub Wiki — Home, Setup Guide, Architecture, Configuration Reference
-- [ ] **AG-04**: README badges: CI, Python, License
-- [ ] **AG-05**: Cross-repo links to org and sibling projects
+- [x] **AG-01**: README rewritten — remove "starter kit" framing, add enterprise positioning — Phase 5 ✓
+- [x] **AG-02**: GitHub Actions CI workflow (Python build) with passing badge — Phase 5 ✓
+- [x] **AG-03**: GitHub Wiki — Home, Setup Guide, Architecture, Configuration Reference — Phase 5 ✓
+- [x] **AG-04**: README badges: CI, Python, License — Phase 5 ✓
+- [x] **AG-05**: Cross-repo links to org and sibling projects — Phase 5 ✓
 
 ### Portfolio Coherence (COH)
 
 - [ ] **COH-01**: Personal OgeonX-Ai profile README linking to Coding-Autopilot-System org
 - [ ] **COH-02**: All three repo READMEs include "Part of Coding-Autopilot-System" badge/link
 - [ ] **COH-03**: Org profile updated with system interaction diagram showing all three projects
 
-## v2 Requirements (Deferred)
+## v2 Requirements — Milestone 2.0 (Full Org Documentation)
+
+### ci-autopilot Emergency Fix (CIAP)
+
+- [ ] **CIAP-01**: Disable/fix runner-health.yml runaway cron (currently `*/15 * * * *` checking offline self-hosted runner)
+- [ ] **CIAP-02**: Bulk-close all 1,964+ open `runner-offline` issues via GitHub API
+- [ ] **CIAP-03**: ci-autopilot Level A docs — README rewrite (AI agent automation framing), CI badge, wiki 4 pages, GitHub topics, cross-links to org
+
+### CAS Secondary Repos (ACOR)
+
+- [ ] **ACOR-01**: autopilot-core Level A docs — README rewrite, CI badge, wiki 4 pages, topics, cross-links
+- [ ] **ACOR-02**: autopilot-demo Level A docs — README rewrite, CI badge, wiki 4 pages, topics, cross-links
+- [ ] **CSEC-01**: cloud-security-service-model documentation — README rewrite (framework/methodology framing), wiki 4 pages, topics
+
+### OgeonX-Ai Core Tech (TECH)
+
+- [ ] **TECH-01**: enterprise-ai-gateway AI engineer reframe — README hero line, architecture diagram, wiki 4 pages, CI badge, cross-links to CAS
+- [ ] **TECH-02**: android AI engineer reframe — scan codebase, README (Android + AI integration framing), wiki 4 pages, CI badge
+
+### OgeonX-Ai Portfolio Repos (PORT)
+
+- [x] **PORT-01**: kim-ai-voice-demo AI engineer reframe — README rewrite (away from ElevenLabs demo framing), wiki 4 pages, topics — Phase 10 ✓
+- [x] **PORT-02**: My-CV reframe — README as AI-powered career tool, wiki 4 pages, topics — Phase 10 ✓
+
+### Cross-Portfolio Coherence (COHER)
+
+- [x] **COHER-01**: GitHub topics audit — all repos have 5-10 accurate, discoverable topics — Phase 11 ✓
+- [x] **COHER-02**: Org pinned repos — manual instructions delivered (no programmatic API; org owner action required) — Phase 11 ✓
+- [x] **COHER-03**: Issue templates — `bug_report.md` and `feature_request.md` in gsd-orchestrator, Promptimprover, autogen — Phase 11 ✓
+
+## v3 Requirements — Milestone 3.0 (gsd-orchestrator Feature Expansion)
+
+### Robustness Foundation (ROB)
+
+- [x] **ROB-01**: Serilog structured logging integrated — all state transitions, errors, and Claude calls emit structured log events — Phase 12 (12-01) ✓
+- [x] **ROB-02**: xUnit test project added with >= 20% coverage on GsdStateMachine and McpStdioClient — Phase 12 (12-03) ✓
+- [x] **ROB-03**: Polly circuit breaker added for MCP tool calls (complements existing retry policy) — Phase 12 (12-02) ✓
+
+### Smarter Issue Triage (TRIAGE)
+
+- [ ] **TRIAGE-01**: `TriagingState` implemented — classifies issue via Claude (actionable / needs-info / duplicate / out-of-scope)
+- [ ] **TRIAGE-02**: Duplicate detection — checks open issues and PRs for similar titles before proceeding
+- [ ] **TRIAGE-03**: `--triage` operating mode — runs triage only, posts classification comment, no code changes
+- [ ] **TRIAGE-04**: Skip logic — issues classified as out-of-scope or duplicate are closed/labelled with comment, workflow exits cleanly
+
+### Autonomous Test Generation (TESTGEN)
+
+- [ ] **TESTGEN-01**: `TestGeneratingState` implemented — Claude generates xUnit tests for files changed in EditingState
+- [ ] **TESTGEN-02**: Generated tests committed to feature branch alongside code changes
+- [ ] **TESTGEN-03**: `ValidatingState` enhanced — checks test file compilation (not runtime pass/fail)
+
+### PR Review Loop (REV)
+
+- [x] **REV-01**: `--pr <N>` operating mode — triggers PR review workflow on a specific PR number
+- [x] **REV-02**: `ReviewingState` enhanced — reads PR diff, Claude produces structured review (issues list with file/line/severity/message)
+- [x] **REV-03**: Review comments posted as inline PR comments via GitHub MCP; approve or request-changes action submitted
+
+### Multi-Repo Support (MULTI)
+
+- [x] **MULTI-01**: `GSD_REPOS` environment variable (JSON array of `{owner, repo}` objects) — replaces single `GSD_GITHUB_OWNER`/`GSD_GITHUB_REPO`
+- [x] **MULTI-02**: `--watch` mode iterates across all configured repos in sequence
+- [x] **MULTI-03**: Checkpointing scoped per repo (`checkpoints/{owner}_{repo}/`)
+- [x] **MULTI-04**: Configurable inter-repo delay (`GSD_REPO_DELAY_SECONDS`) to avoid API rate limits
+
+## v1 Deferred (still out of scope for v2)
 
 - Test suites for gsd-orchestrator, Promptimprover, autogen
 - GitHub Projects board showing roadmap
@@ -68,3 +132,8 @@
 | PI-01–05 | Phase 4 |
 | AG-01–05 | Phase 5 |
 | COH-01–03 | Phase 6 |
+| CIAP-01–03 | Phase 7 |
+| ACOR-01–02, CSEC-01 | Phase 8 |
+| TECH-01–02 | Phase 9 |
+| PORT-01–02 | Phase 10 |
+| COHER-01–03 | Phase 11 |