Session objective

Kick off the scheduled-task hybrid migration to fix repeated PowerShell window-spawning during local task runs. Inventory current footprint, classify keep-local / migrate-cloud / retire, scope Sessions 2 and 3.

What was done

• Pulled cloud-side inventory from SAIL KB: 10 GitHub Actions workflows, 4 Claude Code scheduled tasks, 3 launchd jobs plus 1 stale overlap, and 30 SAIL scheduled tasks routed through Cowork/Claude desktop. Estimated total active footprint: roughly 50 distinct items across 5 runtimes.
• Classified the inventory:
  • Already cloud, no action: 10 GitHub Actions workflows.
  • Migrate to cloud (high leverage): daily-site-health, broken-links-scanner, schema-validator, sitemap-health-check, semrush-site-audit, weekly-cannibalization-fix, weekly-orphan-fixer, ai-visibility-audit, competitive-review-monitor, content-meta-fixer, WP Cron Health Monitor, daily-coding-audit, daily-briefing. Targets are pure-API or read-only, low risk.
  • Keep local, harden: folder-hygiene, downloads-cleanup, skills-library-sync, skills-scheduled-mirror-sync, screaming-frog-ingest, screaming-frog-crawl, outlook-triage, image-audit (pending verify).
  • Retire as duplicates: com.aguiar.screaming-frog-crawl old weekly launchd job; any SAIL task whose function is already a GH Actions workflow.
• Identified PowerShell window-spawning is not Mac-side. Mac launchd and Claude Code tasks use bash/zsh, not pwsh. Likely sources: Windows Task Scheduler on office machine or Codex routines using pwsh as cross-platform shell. Closing this gap is the first Session 2 step.
• Retired session-bootstrapper skill per user directive. Memory edit added: skill no longer loaded, referenced, or chained.
• Cloudflare workers_list call returned no approval. Surfaced as a permission item for Sam to greenlight in Session 2 setup.

Why the session ended

Sam delivered initial direction in chat. Inventory and classification complete. Session 2 picks up cleanly with the Windows Task Scheduler gap, template build, and first migration wave. Session ended at planning checkpoint, well below context pressure.

Recommended next actions

• Session 2: pull full registry.json for remaining 11 task names, inventory Windows Task Scheduler, build two reusable templates (routines/github/_template/ and routines/cloudflare/_template/) reading creds from Notion at runtime, migrate first wave of 4 jobs (daily-site-health, WP Cron Health Monitor, daily-briefing, ai-visibility-audit) as proof of pattern. Harden the keep-local set with hidden-window flags, mutex/lock files, log-to-file detach, PID-check-before-spawn.
• Session 3: finish migration wave, retire confirmed duplicates, create new scheduled-task-architect skill codifying the cloud-first plus safe-local pattern, patch existing skills (screaming-frog-crawl, screaming-frog-ingest, wp-site-health, seo-pulse, batch-indexnow) to default to the safe pattern. Mark folder-cleanup and rename-images as keep-local in their SKILL.md.
• Confirm capacity-watchdog disposition. Not picked in last turn. Default assumption: deferred until after Session 3 unless Sam says otherwise.

Pending decisions awaiting Sam

• A through E on session ordering (recommended: A, proceed with Session 2 as scoped).
• D explicitly: run Windows Task Scheduler inventory via Desktop Commander before Session 2 if Sam confirms the office machine is the PowerShell source.
• AA/BB on Cloudflare always-allow; CC/DD on GitHub workflow write always-allow. Both recommended to avoid per-call approval friction during migration.

Handoff context for next agent

The migration is gated on knowing where the PowerShell windows originate. If you can reach the office Windows machine via Desktop Commander or any remote means, list its Task Scheduler before doing anything else. If not, ask Sam once narrowly: "Which machine spawns the PowerShell windows: office Windows, Mac, or both?" and proceed from there. The cloud-target list above is solid and pre-classified; the templates are the next deliverable. Do not modify live WordPress content from any migrated routine; all writes must be draft-only or read-only. Sam values execution over delegation, so build and verify before reporting back. The 30 SAIL scheduled tasks have a drift-resilient skill-preload header rolled out 2026-05-01; preserve that pattern when migrating any task to cloud. session-bootstrapper is retired; do not reference it.