REVISED 2026-05-31 per Sam: dual-Mac failover, no cloud worker, no Twilio

This supersedes the cloud-first and Twilio direction in the earlier draft of this page and in the execution-update block of the 2026-05-29 session export. Sam has two Macs, usually at least one is on, and prefers a second device as the backup over new paid infrastructure.

The problem

The Daily Morning Briefing ran on one Mac only. If that Mac was asleep or off, the briefing did not run and there was no fallback. Single point of failure on a daily deliverable.

Revised model: two Macs, primary and backup, with a shared run-claim

• Mac A is primary and fires at 7:00. Mac B is backup and fires at 7:15.
• If Mac A is down, Mac B runs at 7:15. If both are up, only one sends, enforced by a claim check.
• iMessage stops being a single point of failure, because whichever Mac is awake sends it, and at least one usually is.

Run-claim mechanism (Notion is the shared state)

• The primary creates that day's "Daily Briefing YYYY-MM-DD" page in the SAIL KB at the START of its run. That page is the claim.
• The backup, at 7:15, checks whether today's page already exists. If yes, the primary handled it, so the backup exits quietly. If no, the primary was down, so the backup runs and creates the page.
• The page status flips to Needs Follow-up at completion. Notion is the coordination point because both Macs reach it over the API with no iCloud sync lag. The local _channel-health.json stays per-device; it is not the shared truth.
• Both-Macs-off case is already covered by the existing 3-day backfill: the next time either Mac wakes, it generates the missed briefing. A total miss self-heals.

Delivery

• Primary mobile channel: iMessage to both recipients (csamaguiar@gmail.com and 15029912491). Works whenever either Mac is up.
• Secondary safety channel: one written drop, either Slack self-DM (recommended, its send API is currently reliable) or Teams self-chat (Sam's preferred comms, but the Pipedream Teams send path has been the chronic failure). Sam to pick one. Neither pushes notifications strongly, so this is a durable copy Sam can pull up, not a primary alert.
• Source of truth: the Notion KB page.

Transition and no-regression

• Both Macs keep their tasks live now. No cutover, nothing to prove first. The two cover each other from day one.
• Back up the current task file on each Mac before any change.