Importance: High. Status: In Progress (web-reachable items Complete; three items need a Mac session).

Continuation. Sam approved 1A (run injector), 2A (reconcile + migrate to canonical repo, always-allow granted), 3A (notification targets), 4A (compare cowork-disk-cleanup vs monthly-dedupe), 5A (repoint scheduler, always-allow granted), and gave his contact info.

Completed this turn

• 3A done: Saved Sam's contact info to Claude memory and wrote it into the Monthly Dedupe Config page. iMessage is live: cell 502-991-2491 plus alternate Apple ID handles csamaguiar@gmail.com and samaguiar1982@gmail.com. Teams DM target still needs Sam's Microsoft 365 UPN (the supplied emails are Apple/Gmail, not a confirmed Teams identity); flagged on the config page and can be resolved via Graph if Sam wants.
• 4A done: Compared the two cleanup skills. NOT redundant. cowork-disk-cleanup clears regenerable caches inside the ephemeral Cowork sandbox (deletes freely, caches regrow); monthly-dedupe dedupes the real Mac home folder and moves irreplaceable user files to Trash with rollback. Different target, cadence, and risk model. No consolidation. cowork-disk-cleanup already carries its own QA-reflection section.
• 2A staged + tooling shipped: Built and validated docs/migrate-skills-to-repo.sh. One-way (live skills -> repo), dry-run by default, never edits live skills, adds only skills absent from the repo, and lists differing skills as conflicts for manual review instead of overwriting. Dry-run against the Cowork mount classified 87 candidate skills and correctly flagged a conflict without clobbering it.
• Confirmed Sam's 2026-05-17 standing permission already authorizes autonomous commits to sail-skills, consistent with the always-allow he reaffirmed on 2A/5A.

Why these three need a Mac session

This is the Claude.ai web/Cowork container. It has no write path to Sam's Mac filesystem or scheduler (read-only skills mount, no Mac SSH, no Desktop Commander wired here). So the following are staged turnkey rather than executed:

• 1A: run docs/apply-selfaudit-to-scheduled-skills.sh against the live skills (idempotent, per-file .bak).
• 2A: run docs/migrate-skills-to-repo.sh --apply after reviewing its dry-run, then git push.
• 5A: repoint the existing "Monthly Home-Folder Duplicate Scan" scheduled task to fire /monthly-dedupe and retire the old read-only body. The exact mechanism (launchd plist, cron, or a Claude/Codex scheduled task) needs Mac inspection to edit precisely.

Recommended next actions

1. In a Claude Code or Cowork session on either Mac, pull sail-skills and run the two committed scripts (self-audit injector, then migration dry-run -> review -> --apply -> push).
2. Decide the canonical resolution for any skills the migration flags as conflicts (repo copy vs live copy).
3. Give Sam's M365/Teams UPN (or approve a Graph lookup) so the Teams ping sends.
4. Inspect and repoint the live monthly-dedupe scheduler.

Handoff for the next agent

All repo changes are plain commits, individually revertable. Both committed scripts are dry-run or idempotent and write backups, so they are safe to run and re-run. The reason the four scheduled skills and the broad migration were not executed from this session is environmental (no Mac write path from web chat), not a blocker in the work itself. When you are on a Mac with the repo checked out, the two scripts in docs/ do the heavy lifting; review their dry-run output before applying. The open architectural question Sam should weigh in on: should the repo be canonical for ALL ~80+ skills (the migration script assumes yes and moves toward it conservatively), or stay a curated subset. GitHub token sourced from Notion API Keys (GITHUB_TOKEN_1), scrubbed after each use.

Pending (awaiting Sam or a Mac session)