0xjitsu · 0xjitsu · Mar 23, 2026 · Mar 23, 2026 · Mar 23, 2026
diff --git a/CLAUDE.md b/CLAUDE.md
@@ -36,12 +36,21 @@ anything-command-center/
                 callback/    # OAuth callback for TikTok
             outreach/
               launch/        # Template-based draft generation
+              send/          # Server-side email send via Gmail API
+              approve/       # Approve/skip drafts (uses lifecycle module)
+              check-rate/    # GET — rate limit status per platform
+            auth/
+              gmail/         # Gmail OAuth flow
+                callback/    # Gmail OAuth callback
+            cron/
+              follow-ups/    # Daily Vercel Cron (9am UTC)
         lib/
+          outreach-lifecycle.ts # Centralized status state machine
           instagram.ts       # Meta Graph API client (stub)
           tiktok.ts          # TikTok API client (stub)
           playwright-dm.ts   # Browser DM automation
           rate-limiter.ts    # Token bucket + circuit breaker
-          gmail.ts           # mailto: URL generator
+          gmail.ts           # Gmail API: sendEmailViaAPI(), token refresh, reply detection
           supabase-server.ts # Server Supabase client
           types.ts           # Creator/OutreachLog interfaces
         components/
@@ -52,13 +61,15 @@ anything-command-center/
           sidebar.tsx        # Navigation
   packages/
     db/                      # Database migrations, seed scripts
-      migrations/            # SQL migration files
+      migrations/            # SQL migration files (001_initial, 002_outreach_automation)
       seed/                  # CSV import scripts
   campaigns/
     templates/               # Outreach message templates (Mustache-style)
-  scout/                     # Python creator discovery scripts
+  scout/                     # Creator discovery + automation scripts
+    dm-automator.ts          # Playwright DM automation (local, persistent browser session)
     data/                    # JSON batch files from scouting runs
   docs/                      # Architecture, schema, and API setup docs
+  vercel.json                # Cron schedule config (follow-up automation)
 ```
 
 ## Key Patterns
@@ -74,16 +85,21 @@ anything-command-center/
 - **Creators Table**: Uses @tanstack/react-table with `VisibilityState` for column toggle (persisted in localStorage). Inline stage editing uses optimistic updates with rollback on failure. Row numbers, profile links, and 9 optional columns (email, region, sub_niche, archetype, specific_hook, engagement_signal, dm_status, source, notes) hidden by default.
 - **Campaign Templates**: Branded for Anything Creator Program with archetype-aware variations (Mega/Macro vs Micro/Rising). Template variables include `{{name}}`, `{{handle}}`, `{{niche}}`, `{{specific_hook}}`, `{{content_idea}}`, `{{sender_name}}`, `{{product_name}}`, `{{product_url}}`, `{{program_name}}`, `{{value_prop}}`.
 - **Rate Limiter**: Token bucket algorithm with per-platform daily caps, warm-up schedule (20/day → 100/day over 4 weeks), random delays (8–15s), and circuit breaker (>10% failure rate pauses sending).
+- **Outreach Lifecycle**: Centralized state machine in `src/lib/outreach-lifecycle.ts`. Events (`draft_created`, `initial_sent`, `follow_up_1_sent`, `follow_up_2_sent`, `reply_detected`, `sequence_complete`) drive automatic `stage` and `dm_status` transitions on the creator record. The `/api/outreach/approve` route uses this module instead of hardcoded status logic.
+- **Gmail API**: `src/lib/gmail.ts` provides `sendEmailViaAPI()` with RFC 2822 MIME formatting, automatic token refresh, and reply detection via Gmail readonly scope. Settings page shows Connect/Disconnect state. DraftCard calls the API when connected, falls back to `mailto:` when not.
+- **Follow-Up Cron**: `/api/cron/follow-ups` runs daily at 9am UTC via Vercel Cron (configured in `vercel.json`). Checks for replies before generating follow-ups, auto-sends email follow-ups if Gmail API is connected, queues DM follow-ups as drafts for human review, and auto-completes sequences 7 days after FU2 with no reply.
+- **DM Focus Mode**: The OutreachQueue "DM Focus" tab presents one DM at a time with an editable textarea, progress bar, rate limit badges (X/Y platform today, warm-up week N), and a confirm-before-sent dialog.
 - **Playwright Automation**: Opens creator DM page in persistent browser session, pre-fills personalized message, human reviews and clicks Send. Never fully automated for cold outreach.
+- **DM Automator** (`scout/dm-automator.ts`): Local Playwright script for Instagram/TikTok DMs. Fetches queue from API, respects rate limits, uses persistent browser session (login once, reuse cookies). Requires local execution — not deployed to Vercel.
 
 ## Database
 
 - **Supabase project**: Configure via environment variables
-- **Migration**: Run `packages/db/migrations/001_initial.sql` in the Supabase SQL editor
+- **Migration**: Run `packages/db/migrations/001_initial.sql` and `002_outreach_automation.sql` in the Supabase SQL editor
 - **Seed**: `cd packages/db && pnpm seed` (requires `.env` with `SUPABASE_URL` and `SUPABASE_SERVICE_ROLE_KEY`)
 - **Tables**:
   - `creators` — main CRM table (columns: `stage`, `score`, `followers` as INTEGER)
-  - `outreach_log` — message history
+  - `outreach_log` — message history (includes `scheduled_for`, `parent_outreach_id`, `gmail_message_id` columns from migration 002)
   - `rate_limit_state` — per-platform rate limit tracking (token bucket state, circuit breaker)
   - `oauth_tokens` — stored OAuth access/refresh tokens for connected platforms
 
@@ -94,7 +110,7 @@ anything-command-center/
 | `/` | Main dashboard — creator table with filters, search, pipeline view |
 | `/import` | Bulk import creators from CSV or JSON files |
 | `/guide` | Setup guide and onboarding documentation |
-| `/settings` | Platform connections (OAuth), rate limit config |
+| `/settings` | Platform connections (OAuth for Instagram, TikTok, Gmail), rate limit config |
 | `/analytics` | Pipeline funnel visualization, outreach stats |
 
 ## Testing
@@ -106,7 +122,9 @@ anything-command-center/
 
 - Vercel auto-deploys from `main` branch
 - Preview deploys on pull requests
-- Environment variables must be set in Vercel project settings
+- Environment variables must be set in Vercel project settings (including `CRON_SECRET` and Gmail OAuth vars)
+- Vercel Cron configured in `vercel.json` for daily follow-up automation (9am UTC)
+- Run `002_outreach_automation.sql` migration before deploying outreach features
 - Live at: https://anything-command-center.vercel.app
 
 ## Campaign Templates
@@ -133,3 +151,5 @@ Located in `campaigns/templates/`:
 | `META_PAGE_ID` | Facebook Page ID connected to Instagram Business account |
 | `TIKTOK_CLIENT_KEY` | TikTok app Client Key (from developers.tiktok.com) |
 | `TIKTOK_CLIENT_SECRET` | TikTok app Client Secret |
+| `CRON_SECRET` | Secret token to authenticate Vercel Cron job requests |
+| `GMAIL_REDIRECT_URI` | Gmail OAuth callback URL (`https://your-app.vercel.app/api/auth/gmail/callback`) |
diff --git a/README.md b/README.md
@@ -62,15 +62,19 @@ cd ../.. && pnpm dev
 | Column Visibility | Live | Show/hide optional columns (email, region, hook, DM status, etc.) with localStorage persistence |
 | Profile Links | Live | Dedicated column with direct links to creator's social profile |
 | Outreach Queue | Live | Draft, review, and send personalized messages |
+| DM Focus Mode | Live | One-DM-at-a-time queue with editable textarea, progress bar, rate limit badges |
 | Send DM Flow | Live | Copy message to clipboard + open creator's profile in new tab in one click |
 | Campaign Templates | Live | Anything-branded cold DM, cold email, follow-up sequences with archetype-aware variations |
 | CSV Import | Live | Upload CSV, map columns, preview, batch insert |
 | Analytics | Live | Pipeline funnel, platform distribution, conversion metrics |
 | Rate Limiter | Live | Per-platform caps, warm-up schedule, circuit breaker |
-| OAuth Connections | Live | Connect Instagram (Meta) and TikTok accounts via Settings page |
+| Outreach Lifecycle | Live | Centralized state machine for outreach status transitions (draft → sent → follow-ups → complete) |
+| Gmail API | Live | OAuth connect/disconnect, RFC 2822 send, token refresh, reply detection |
+| Follow-Up Automation | Live | Daily Vercel Cron job: reply detection, auto-send email follow-ups, queue DM follow-ups as drafts |
+| OAuth Connections | Live | Connect Instagram (Meta), TikTok, and Gmail accounts via Settings page |
 | Instagram DMs | Planned | Meta Graph API (warm) + browser automation (cold) |
 | TikTok DMs | Planned | TikTok API (warm) + browser automation (cold) |
-| Gmail | MVP | mailto: links with pre-filled subject/body |
+| DM Automator | Planned | Local Playwright script for Instagram/TikTok DMs with persistent browser session |
 
 ## Pipeline Stages
 
@@ -93,6 +97,8 @@ Prospect → Contacted → Replied → Negotiating → Onboarded → Active
 | `META_APP_SECRET` | Meta/Facebook app secret |
 | `TIKTOK_CLIENT_KEY` | TikTok developer client key |
 | `TIKTOK_CLIENT_SECRET` | TikTok developer client secret |
+| `CRON_SECRET` | Secret token to authenticate Vercel Cron jobs |
+| `GMAIL_REDIRECT_URI` | Gmail OAuth callback URL (e.g., `https://your-app.vercel.app/api/auth/gmail/callback`) |
 
 ## Project Structure
 
@@ -102,18 +108,32 @@ anything-command-center/
 │   └── command-center/          # Next.js 16 dashboard
 │       └── src/
 │           ├── app/             # App Router pages + API routes
+│           │   └── api/
+│           │       ├── outreach/
+│           │       │   ├── send/        # Server-side email send with rate limiter
+│           │       │   └── check-rate/  # Rate limit status per platform
+│           │       ├── auth/
+│           │       │   └── gmail/       # Gmail OAuth flow + callback
+│           │       └── cron/
+│           │           └── follow-ups/  # Daily Vercel Cron (9am UTC)
 │           ├── components/      # React components (shadcn/ui)
-│           └── lib/             # Supabase, rate limiter, social APIs
+│           └── lib/
+│               ├── outreach-lifecycle.ts  # Status state machine
+│               ├── gmail.ts              # Gmail API: send, token refresh, reply detection
+│               ├── rate-limiter.ts       # Token bucket + circuit breaker
+│               └── supabase-server.ts    # Server Supabase client
 ├── packages/
 │   └── db/                      # Database layer
-│       ├── migrations/          # SQL schema (4 tables)
+│       ├── migrations/          # SQL schema (001_initial + 002_outreach_automation)
 │       └── seed/                # CSV + JSON import scripts
 ├── campaigns/
 │   └── templates/               # Outreach message templates
-├── scout/                       # Python creator discovery pipeline
+├── scout/                       # Creator discovery + automation
 │   ├── *.py                     # Discovery + verification scripts
+│   ├── dm-automator.ts          # Playwright DM automation (local, human-in-the-loop)
 │   └── data/                    # JSON batch outputs (800+ creators)
 ├── docs/                        # Architecture docs
+├── vercel.json                  # Cron schedule config
 ├── CLAUDE.md                    # AI assistant context
 └── pnpm-workspace.yaml          # Monorepo config
 ```
@@ -129,6 +149,11 @@ anything-command-center/
 | GET | `/api/outreach` | List outreach queue by status |
 | POST | `/api/outreach/launch` | Generate draft messages for selected creators |
 | POST | `/api/outreach/approve` | Approve/skip outreach drafts |
+| POST | `/api/outreach/send` | Send email via Gmail API (falls back to mailto:) |
+| GET | `/api/outreach/check-rate` | Rate limit status per platform (X/Y today, warm-up week) |
+| GET | `/api/auth/gmail` | Initiate Gmail OAuth flow |
+| GET | `/api/auth/gmail/callback` | Gmail OAuth callback — stores tokens |
+| POST | `/api/cron/follow-ups` | Daily follow-up cron (reply detection, auto-send, sequence completion) |
 | POST | `/api/import` | Bulk import creators from CSV |
 | GET | `/api/analytics` | Pipeline stage counts + conversion metrics |
 
@@ -143,6 +168,43 @@ anything-command-center/
 
 Safety: Circuit breaker auto-pauses if >10% failure rate in last 25 sends (30-min pause).
 
+## Outreach Automation
+
+The outreach system is split between automated and human-in-the-loop actions:
+
+**Automated (server-side):**
+- Email sending via Gmail API (OAuth connected)
+- Follow-up scheduling: daily Vercel Cron at 9am UTC (`/api/cron/follow-ups`)
+- Reply detection via Gmail readonly scope before generating follow-ups
+- Auto-send email follow-ups when Gmail API is connected
+- Auto-complete sequences 7 days after FU2 with no reply
+
+**Human-in-the-loop (manual review required):**
+- DM follow-ups are queued as drafts for human review in the DM Focus tab
+- Cold DMs require manual send (copy + open profile, or local DM automator)
+- Confirm-before-sent dialog prevents accidental DM status marks
+
+**Lifecycle State Machine** (`src/lib/outreach-lifecycle.ts`):
+- Events: `draft_created` → `initial_sent` → `follow_up_1_sent` → `follow_up_2_sent` → `reply_detected` → `sequence_complete`
+- Automatically advances both `stage` and `dm_status` on the creator record
+
+## DM Automation Setup
+
+The DM automator (`scout/dm-automator.ts`) runs locally via Playwright for Instagram/TikTok DMs:
+
+1. Install dependencies: `cd scout && pnpm install`
+2. Log into Instagram/TikTok in the Playwright browser session (one-time)
+3. The script fetches the DM queue from `/api/outreach/check-rate`, respects rate limits
+4. Uses persistent browser session (cookies reused across runs)
+5. Human reviews each DM before confirming send
+
+## Deployment Checklist
+
+- Set all environment variables in Vercel (including `CRON_SECRET` and Gmail OAuth vars)
+- Run `packages/db/migrations/002_outreach_automation.sql` in Supabase SQL editor
+- Configure Gmail OAuth redirect URI to `https://your-app.vercel.app/api/auth/gmail/callback`
+- Verify Vercel Cron is active (`vercel.json` includes the follow-up schedule)
+
 ## Deployment
 
 - **Production**: Auto-deploys from `main` via Vercel

diff --git a/apps/command-center/package.json b/apps/command-center/package.json
@@ -10,6 +10,7 @@
   },
   "dependencies": {
     "@radix-ui/react-accordion": "^1.2.12",
+    "@radix-ui/react-alert-dialog": "^1.1.15",
     "@radix-ui/react-checkbox": "^1.3.3",
     "@radix-ui/react-dialog": "^1.1.15",
     "@radix-ui/react-dropdown-menu": "^2.1.16",

diff --git a/apps/command-center/src/app/(dashboard)/creators/[id]/page.tsx b/apps/command-center/src/app/(dashboard)/creators/[id]/page.tsx
@@ -16,7 +16,7 @@ import {
 import { PlatformBadge } from "@/components/platform-icon"
 import { PipelineBadge } from "@/components/pipeline-badge"
 import type { Creator, PipelineStage, OutreachLog, OutreachChannel } from "@/lib/types"
-import { sendViaGmail } from "@/lib/gmail"
+import { generateMailtoUrl } from "@/lib/gmail"
 import {
   ArrowLeft,
   Rocket,
@@ -155,19 +155,38 @@ export default function CreatorDetailPage({
 
   const handleApproveAndSend = async (log: OutreachLog) => {
     if (!creator) return
-    if (log.channel === "email" && creator.email) {
-      const result = await sendViaGmail({
-        outreachId: log.id,
-        to: creator.email,
-        subject: log.subject || "",
-        body: log.content,
+    if (log.channel === "email") {
+      // Try server-side Gmail API send first
+      const sendRes = await fetch("/api/outreach/send", {
+        method: "POST",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ outreach_id: log.id }),
       })
-      if (result.success) {
-        toast.success("Email opened in mail client and marked as sent!")
+
+      if (sendRes.ok) {
+        toast.success(`Email sent to ${creator.email} via Gmail API!`)
         fetchCreator()
-      } else {
-        toast.error(result.error || "Failed to send")
+        return
       }
+
+      // Fallback to mailto: if Gmail API not connected
+      if (creator.email) {
+        const url = generateMailtoUrl({
+          to: creator.email,
+          subject: log.subject || "",
+          body: log.content,
+        })
+        window.open(url, "_blank")
+      }
+
+      // Mark as sent via approve endpoint
+      await fetch("/api/outreach/approve", {
+        method: "POST",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ outreach_id: log.id, action: "send" }),
+      })
+      toast.success("Email opened in mail client and marked as sent!")
+      fetchCreator()
     } else {
       // For DMs, just mark as sent
       try {

diff --git a/apps/command-center/src/app/(dashboard)/settings/page.tsx b/apps/command-center/src/app/(dashboard)/settings/page.tsx
@@ -133,9 +133,13 @@ function SettingsPageInner() {
       toast.success("Instagram connected successfully!")
     } else if (connected === "tiktok") {
       toast.success("TikTok connected successfully!")
+    } else if (connected === "gmail") {
+      toast.success("Gmail connected! Emails will now send via Gmail API.")
     }
 
-    if (error === "instagram_not_configured") {
+    if (error === "gmail_not_configured") {
+      toast.error("Set up GOOGLE_CLIENT_ID in Vercel environment variables first")
+    } else if (error === "instagram_not_configured") {
       toast.error("Set up META_APP_ID in Vercel environment variables first")
     } else if (error === "tiktok_not_configured") {
       toast.error("Set up TIKTOK_CLIENT_KEY in Vercel environment variables first")
@@ -267,27 +271,8 @@ function SettingsPageInner() {
       )
     }
 
-    // Gmail is always connected
-    if (platform === "gmail") {
-      return (
-        <div className="flex items-center justify-between rounded-lg border p-4">
-          <div className="flex items-center gap-3">
-            {icon}
-            <div>
-              <p className="text-sm font-medium">{label}</p>
-              <p className="text-xs text-muted-foreground">{description}</p>
-            </div>
-          </div>
-          <Badge
-            variant="outline"
-            className="border-emerald-500/50 text-emerald-500"
-          >
-            <CheckCircle2 className="mr-1 h-3 w-3" />
-            Connected
-          </Badge>
-        </div>
-      )
-    }
+    // Gmail: show OAuth connect/disconnect (same as other platforms)
+    // Falls through to the standard connected/not-connected logic below
 
     const status = authStatus?.[platform]
 
@@ -420,7 +405,7 @@ function SettingsPageInner() {
             "gmail",
             <Mail className="h-5 w-5 text-red-400" />,
             "Gmail",
-            "Send emails via mailto: protocol"
+            "Send emails via Gmail API (connect to automate sending)"
           )}
           {renderPlatformRow(
             "instagram",