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Email System Runbook

Email System Runbook

Overview

Centralized email system for ALAI/BasicAS. All outbound email goes through IMAP/SMTP (one.com + domeneshop), with a single audit database tracking everything.

Accounts

Account Email Provider Usage
john [email protected] one.com Primary business email
info [email protected] one.com General inquiries
alai [email protected] domeneshop ALAI branded, signing emails

Credentials stored in Vaultwarden (bw get item "Email - [email protected]").

How to Send Email

Option 1: MCP (from Claude session — PREFERRED)

mcp__email__email_send({
  account_name: "john",
  to: "[email protected]",
  subject: "Subject",
  body: "Body text",
  body_type: "html",          // or "plain"
  attachments: [{path: "/absolute/path/file.pdf"}]  // optional
})

Option 2: CLI (from scripts, daemons, agents)

node ~/system/tools/mail-native.js send \
  --to [email protected] \
  --subject "Subject" \
  --body "Body text" \
  --account john \
  --attachment /path/to/file.pdf   # optional, comma-separated for multiple

Option 3: Signing Emails (DocuSeal)

node ~/system/tools/send-signing-email.js send <template_id> '<signer_json>' --test

How to Read Email

MCP (preferred)

mcp__email__emails_find({account_name: "john", query: "invoice", limit: 10})
mcp__email__email_respond({email_id: "12345", body: "Reply text"})

CLI

node ~/system/tools/mail-native.js search "invoice" --account john --limit 20
node ~/system/tools/mail-native.js read <uid> --account john
node ~/system/tools/mail-native.js unread --account john
node ~/system/tools/mail-native.js reply <uid> --body "Reply text"
node ~/system/tools/mail-native.js forward <uid> --to [email protected]
node ~/system/tools/mail-native.js attachment <uid> --save /tmp/downloads

Email Audit (Single Source of Truth)

Database: ~/system/databases/email-audit.db

Every outbound email is logged here, regardless of send path:

  • mail-native.js — hard require, logs on every send/reply/forward
  • MCP bridge — logs via JS module + Python hook (dedup by message_id)
  • signing email — logs via JS module
  • Hook safety net — email-outbox-logger.py catches MCP sends even if JS fails

Quick Commands

node ~/system/tools/email-audit.js recent               # Last 10 sent emails
node ~/system/tools/email-audit.js find "client name"    # Search all emails
node ~/system/tools/email-audit.js find "invoice" --days 30  # Last 30 days
node ~/system/tools/email-audit.js stats --days 7        # Stats by tool/account
node ~/system/tools/email-audit.js health                # System health check
node ~/system/tools/mail-native.js audit --days 30       # Audit from CLI
node ~/system/tools/mail-native.js sent --account john   # IMAP Sent folder

Architecture

Send paths:
  MCP (email_send/respond) ──┐
  mail-native.js CLI ────────┤──→ email-audit.db (single source of truth)
  send-signing-email.js ─────┤
  Hook (email-outbox-logger) ─┘ (safety net, dedup by message_id)

DEPRECATED Tools (DO NOT USE)

Tool Replacement
email.js mail-native.js
email-monitor.js MCP bridge
email-outbox.db email-audit.db
Inline SMTP scripts BLOCKED by bash-security-gate.py

Email-to-Task Integration

Automatic Task Creation

The email-agent daemon (~/system/daemons/email-agent.js) automatically creates MC tasks for ACTION emails:

  • Classifies incoming emails as ACTION/FYI/SPAM
  • Creates MC task for ACTION emails via email-to-task.js
  • Links email record to MC task via mc_task_id column

Backlog Processing (MC #9269)

On daemon startup, email-agent processes ACTION emails that missed MC task creation:

SELECT id, message_id, account, from_addr, from_name, subject, date, action_needed, summary, priority
FROM emails
WHERE classification = 'ACTION' AND mc_task_id IS NULL
ORDER BY date DESC

How it works:

  1. Query runs once per daemon startup (before new email processing)
  2. For each backlog email: calls email-to-task.js with full context
  3. Extracts MC task ID from output (MC task #1234)
  4. Updates email record: UPDATE emails SET mc_task_id = ? WHERE id = ?
  5. Non-blocking: errors logged but don't crash daemon

Idempotency: Duplicate detection handled by mc.js (same title + <24h → link to existing task)

Removed 24h cutoff (2026-04-25):

  • Old logic: Only process emails from last 24h
  • New logic: Process ALL ACTION emails without mc_task_id (no time filter)
  • Reason: 78 ACTION emails backlogged over weeks — cutoff prevented recovery

Manual Backfill Procedure

If ACTION emails accumulate without MC tasks:

# 1. Check backlog count
sqlite3 ~/system/databases/email-inbox.db \
  "SELECT COUNT(*) FROM emails WHERE classification='ACTION' AND mc_task_id IS NULL;"

# 2. Restart daemon (triggers backlog processing)
launchctl kickstart -k gui/$(id -u)/com.john.email-agent

# 3. Verify log
tail -50 ~/system/logs/email-agent.log | grep -A10 "BACKLOG PROCESSING"

# 4. Check result
sqlite3 ~/system/databases/email-inbox.db \
  "SELECT COUNT(*) FROM emails WHERE classification='ACTION' AND mc_task_id IS NULL;"

Reference: /tmp/mc-9269-completion-report.md — 2026-04-25 backfill (78 emails → 69 MC tasks)

Troubleshooting

Email not in audit

  1. Check node email-audit.js recent — is it really missing?
  2. Check MCP bridge log: tail ~/system/logs/email-mcp-bridge.log
  3. Check mail-native log: tail ~/system/logs/mail-native.log
  4. Run node email-audit.js health — any warnings?

SMTP connection fails

  1. Check vault: bw get item "Email - [email protected]" --session $(cat /tmp/bw-session) | jq .login.username
  2. Test: node mail-native.js test --account john
  3. one.com rate limits: wait 5 min, retry

Attachments not working

  1. Verify file exists: ls -la /path/to/file
  2. Use absolute paths only
  3. Max attachment size: ~25MB (one.com limit)
  4. CLI: --attachment /path/file1.pdf,/path/file2.pdf (comma-separated)
  5. MCP: attachments: [{path: "/abs/path"}] (array of objects)

ACTION email has no MC task

Symptoms: Email classified as ACTION but mc_task_id IS NULL in database

Diagnosis:

# Check specific email
sqlite3 ~/system/databases/email-inbox.db \
  "SELECT id, from_addr, subject, classification, mc_task_id FROM emails WHERE id = <email_id>;"

# Check backlog count
sqlite3 ~/system/databases/email-inbox.db \
  "SELECT COUNT(*) FROM emails WHERE classification='ACTION' AND mc_task_id IS NULL;"

Fix:

  1. Check daemon is running: launchctl list | grep email-agent
  2. Check daemon log: tail -100 ~/system/logs/email-agent.log
  3. Trigger backlog processing: launchctl kickstart -k gui/$(id -u)/com.john.email-agent
  4. If still NULL after daemon cycle:
    • Manual task creation: node ~/system/tools/email-to-task.js --from "..." --subject "..." --message-id "..."
    • Update email record: sqlite3 ~/system/databases/email-inbox.db "UPDATE emails SET mc_task_id = <task_id> WHERE id = <email_id>;"
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