Steps

1. Get today's due tasks from Todoist

source {user.workspace}/.env
todoist-cli today --json

Also check overdue tasks:

todoist-cli list --filter "overdue" --json

2. Identify email/ping tasks

Filter for tasks whose content matches outreach intent:

• Keywords: ping, email, follow up, follow-up, send, reach out, text, message, intro, connect, check in, nudge, reply, respond, draft
• Pattern: any task that implies sending a communication to a specific person

Skip tasks that are clearly NOT outreach (e.g. "review doc", "read report", "build proposal").

3. For each outreach task, draft the email

Read and follow ~/executive-assistant-skills/email-drafting/SKILL.md for all drafting rules.

For each task:

1. Identify the recipient: Extract person/company name from task content + description
2. Pull meeting context (if available): If the task description references a meeting name, date, or was created by the action-items cron (check for Granola citation links or meeting metadata in description), retrieve the transcript via Granola/Grain. If no meeting reference exists in the task, skip directly to step 3 — draft from email history and task content alone.

   # Find the meeting in Granola
   mcporter call granola list_meetings --args '{"time_range": "custom", "custom_start": "<meeting-date>", "custom_end": "<meeting-date+1>"}'
   # Query for what was discussed with this person
   mcporter call granola query_granola_meetings --args '{"query": "What did {user.name} discuss with <recipient> and what did he promise or commit to do?", "document_ids": ["<meeting_id>"]}'

Then cross-check with Grain for the full transcript:

   mcporter call grain.list_attended_meetings --args '{}'
   # Note: Grain's schema does not support `start_date`/`end_date` filters. Call with empty args and filter the results manually by `start_datetime` to match the meeting date range.
   mcporter call grain.fetch_meeting_transcript --args '{"meeting_id": "<grain_meeting_id>"}'

When meeting context is available, the email draft must reflect what was actually said — not just the task title. Look for: specific commitments, timelines discussed, names/projects mentioned, tone of the conversation, and any docs/links promised.

1. Search email history: Find the latest thread with this person across both Gmail accounts to get context, their email address, and the right account to reply from. If no prior thread exists with this recipient, default to {user.workemail} for professional/business contacts or {user.primaryemail} for personal contacts. When ambiguous, use {user.work_email}.
2. Determine email type: follow-up, ping/check-in, intro, send-doc, etc.
3. Draft the email: Create a Gmail draft on the correct account (the one with the existing thread). If it's a reply, use --thread-id to keep it in the same thread.
4. Use all context together: Combine the meeting transcript (what was actually discussed), task description, and email history to write a specific, contextual draft. Never write generic follow-ups — reference concrete topics from the conversation.

Draft rules

• Mirror the language of the existing thread (English or Spanish)
• Keep it short — these are follow-ups and pings, not essays
• Sign with {user.signature}
• If the task says "ping" or "check in" — write a brief, friendly nudge
• If the task says "send [thing]" — draft the email with the attachment reference (or attach if path is known)
• If the task says "intro" — follow intro format from email-drafting skill
• If recipient email can't be found — report it, don't skip silently

4. Notify via WhatsApp

Send a single WhatsApp message to {user.whatsapp} with:

📬 *Due-today drafts*

<N> email drafts created from today's Todoist tasks:

1. **<recipient>** — <one-line intent> (draft in <account>)
2. ...

Review and send when ready.

If tasks exist but none are outreach-type, report:

📋 *Due-today tasks (no drafts needed)*

<list of today's tasks — quick reference>

If no tasks due today → NO_REPLY (skip notification entirely).

5. Infrastructure

python3 {user.workspace}/scripts/cron_canary.py ping todoist-due-drafts

Error handling

• If todoist-cli fails: notify via WhatsApp "⚠️ Todoist due-drafts failed: ", ping canary, exit.
• If Granola/Grain lookup fails for a task: continue without meeting context — draft from email history + task content only.
• If Gmail draft creation fails for one task: continue with remaining tasks, report failures in the notification.
• If no .env file or token expired: report "⚠️ Todoist token unavailable — check agent-secrets lease" and exit.

Rules

• Don't complete the tasks — just draft and notify. User decides when to send.
• Before drafting, check if user already replied: gog --account --no-input gmail search "to: in:sent newer_than:14d" --json. If recent sent mail exists in the same thread, skip drafting and note "already replied" in the notification.
• Check for existing drafts before creating: gog --account --no-input gmail drafts --json. If a draft already exists for the same thread (matching thread ID or recipient + subject), skip and note "draft already exists."
• Overdue outreach tasks get a ⚠️ prefix in the notification.