# Outbound Email Follow-Up Tracker

*Spec — February 14, 2026*
*Status: Parked, ready to build*

---

## Problem

Johan sends emails that require responses. If no reply comes, nobody notices until he manually remembers to check. Conversations also move to phone/WhatsApp/in-person — so "no email reply" doesn't always mean "not handled."

## Solution

Triage outgoing emails the same way we triage incoming: K2.5 reads each sent email and decides if it expects a reply. If yes, track it with a deadline. If the deadline passes with no reply, push one alert to Fully. Dismiss via Fully or auto-resolve on inbound reply.

## Architecture

Everything lives in MC. Fully is just the display layer.

### IMAP Changes

Add Sent folder polling to existing connectors:
- `tj_jongsma_me` → poll `Sent` alongside `INBOX`
- `johan_jongsma_me` → poll `Sent` alongside `INBOX`

Tag outgoing messages with `direction: "outbound"` in MC's message store (inbound messages get `direction: "inbound"` or remain untagged for backwards compat).

### Schema: `follow_ups` table (orchestration.db)

```sql
CREATE TABLE follow_ups (
  id TEXT PRIMARY KEY,           -- MC message ID of the outbound email
  to_address TEXT NOT NULL,       -- recipient email
  to_name TEXT,                   -- recipient display name
  subject TEXT,                   -- email subject
  sent_at TEXT NOT NULL,          -- ISO timestamp
  deadline_hours INTEGER DEFAULT 48,  -- expected response window
  expects_reply INTEGER DEFAULT 1,    -- 1=yes, 0=no (triage decided no)
  reply_received INTEGER DEFAULT 0,   -- auto-set on inbound match
  reply_message_id TEXT,          -- MC message ID of the inbound reply
  alerted_at TEXT,                -- timestamp when Fully alert was pushed (NULL = not yet)
  dismissed INTEGER DEFAULT 0,    -- set via Fully callback
  dismissed_at TEXT,              -- timestamp
  created_at TEXT DEFAULT (datetime('now'))
);
```

### Triage (K2.5)

Same triage engine, second pass for outbound messages. Prompt addition:

```
For OUTBOUND emails, determine:
1. Does this email expect a reply? (question, request, proposal, scheduling = yes. FYI, acknowledgment, thank you = no)
2. How urgent is the expected reply?
   - urgent: 24h (time-sensitive, medical, financial)
   - normal: 48h (business correspondence, requests)  
   - low: 7d (informational, low-priority asks)
3. Output: { "expects_reply": true/false, "deadline_hours": 24|48|168 }
```

### Alert Flow

**Check runs every hour (cron or heartbeat):**

```
SELECT * FROM follow_ups 
WHERE expects_reply = 1 
  AND reply_received = 0 
  AND dismissed = 0 
  AND alerted_at IS NULL 
  AND datetime(sent_at, '+' || deadline_hours || ' hours') < datetime('now')
```

For each result:
1. POST to Fully: `{ "message": "🟠 No reply from {to_name} re: {subject} — sent {N} days ago", "priority": "warning" }`
2. SET `alerted_at = now()`
3. **Never alert again for this follow-up**

### Auto-Resolve

When an inbound email arrives, check if sender matches any active follow-up:

```
UPDATE follow_ups 
SET reply_received = 1, reply_message_id = ? 
WHERE to_address = ? 
  AND reply_received = 0 
  AND dismissed = 0
ORDER BY sent_at DESC 
LIMIT 1
```

Match by email address. Thread matching (In-Reply-To header) is better but address matching covers 90% of cases and is simpler.

### Fully Dismiss Callback

When a follow-up alert is dismissed on Fully (long-press done or ×):

Alert dashboard POSTs to MC:
```
POST /api/follow-ups/{id}/dismiss
```

MC sets `dismissed = 1, dismissed_at = now()`.

This requires:
1. Follow-up alerts include the MC follow-up ID in their metadata
2. Alert dashboard `removeAlert` / done handler checks for follow-up ID and calls MC

### Auto-Expire

Follow-ups that were alerted but not dismissed auto-expire after 14 days:

```
UPDATE follow_ups SET dismissed = 1 
WHERE alerted_at IS NOT NULL 
  AND dismissed = 0 
  AND datetime(alerted_at, '+14 days') < datetime('now')
```

Runs on the same hourly check.

## Edge Cases

- **Reply via WhatsApp/phone:** Johan dismisses the Fully alert. That's the signal.
- **Multiple emails to same person:** Each gets its own follow-up. Inbound reply resolves the most recent one.
- **CC/BCC recipients:** Only track the TO address. CC'd people rarely owe a reply.
- **Auto-replies/OOO:** Don't count as a real reply. Triage can detect these.
- **Johan replies again (bump):** If Johan sends a second email to the same person on the same thread, reset the deadline on the existing follow-up.

## Implementation Order

1. Add Sent folder to IMAP connectors
2. Add `direction` field to MC message model
3. Create `follow_ups` table
4. Add outbound triage prompt to K2.5
5. Add follow-up check to hourly cron / heartbeat
6. Add auto-resolve on inbound match
7. Add dismiss callback endpoint in MC
8. Wire alert dashboard to call MC on dismiss
9. Add auto-expire cleanup

## Not In Scope (Yet)

- WhatsApp outbound tracking (could add later, same pattern)
- Calendar meeting follow-ups (different trigger, same tracker)
- Priority escalation (if 2x deadline passes, escalate from 🟠 to 🔴)