Importance: Medium. This was a dry test, not a production run. No files were modified anywhere. The value is in what the test exposed.

Done vs pending: Test DONE. It surfaced one real blocker and two hygiene items, all PENDING Sam's call.

What was tested and how

Handed the lean rewrite to a cold agent (this session, no extra context) and executed it as written to see how far it gets from the cloud. The skill says: read truth from the SAIL KB config page and the sail-skills repo, reconcile the mirrors, degrade rather than abort.

What the test found

Reachable from the cloud environment: Notion (config lookup, prior run logs, KB export) and the GitHub sail-skills repo (read). Not reachable: Sam's Mac filesystem. This ran in a Linux sandbox, SAIL_DOCS unset, the Mac Skills and Claude/Scheduled trees absent.

The decisive finding: the two canonical skills this task is supposed to mirror, post-run-qa-reflection and sail-kb-daily-pulse, are NOT in the sail-skills repo. Combined with the mirror destination being Mac-local, both sides of the reconciliation live only on the Mac. So from the cloud there was nothing to compare and nothing to write. The skill degraded gracefully and produced a report naming exactly what could not be computed, which is the behavior the rewrite intended.

Three things worth acting on:

1. This task is structurally Mac-local. It can only do its real job where the local trees resolve: Cowork desktop or Claude Code on Sam's machine. No skill rewrite changes that.
2. The lean skill's premise that truth lives in Notion plus the repo is only half true for THIS task, because its canonicals are not in the repo yet. That is fixable and aligns with the cloud-migration goal.
3. Repo housekeeping drift: the retired session-bootstrapper folder still exists in sail-skills/skills, and a banana-router folder is present.

Production context that supports the design: the May 28 prior run already degraded on a missing surface-check script, so graceful degradation is the normal mode for this task, not an edge case.

Why the session is ending

The test is complete and the next moves are Sam's decisions: where this task should run, whether to push the canonicals to the cloud, and the repo cleanup. Holding on those rather than acting unprompted on the repo or his machine.

Recommended next actions (none blocking)

1. Decide the home for this task: keep it Mac-local (run via Cowork desktop or Claude Code), or make it cloud-capable by pushing the two canonicals to the sail-skills repo. The second matches the stated cloud-first direction.
2. Remove the retired session-bootstrapper folder from the repo (and decide banana-router), with a one-commit rollback.
3. Create the SAIL KB config page the lean skill references, so config stops living in the skill body.

Handoff for the next agent

The deliverable is the test-run report. The blocker is environmental, not a skill bug: this task's canonical source and mirror destination both live on the Mac, and the canonicals are not mirrored to GitHub, so a cloud agent cannot reconcile them. If Sam wants this to run from the cloud, the prerequisite is getting post-run-qa-reflection and sail-kb-daily-pulse into sail-skills. If he keeps it Mac-local, the lean skill is fine as written; just run it where the local trees exist. You are assumed as capable as this session; treat the next actions as options.