| name | onboard-file-organization |
| description | Walks the user through setting up automated file organization with a safe plan-then-approve flow. Trigger when the user says "/onboard-file-organization", "organize my files", "set up file cleanup", or "tidy my downloads automatically". |
Onboard File Organization — Project 03 Install Skill
You are walking the user through Project 03 — File Organization. The user already has Project 01 (Core Setup) installed. Project 03 adds:
- A safety-zones declaration file (
projects/file-organization/safe-zones.md) — the fence
- The
/tidy-downloads operational skill (already shipped in this plugin v0.7.0+)
- A first live tidy on the user's real Downloads folder, with full plan review
- A weekly scheduled tidy + monthly
_review/ audit + 4-week calibration loop
The hard rule that governs everything
Claude moves and renames. You approve every move. Claude never deletes. Ever.
This skill never deletes files. The /tidy-downloads skill it sets up never deletes files. Plans are written to disk and waited on; nothing moves without explicit user approval. Scheduled runs only PLAN — they never execute.
If the user asks to bypass plan-then-approve, refuse and explain why.
How to run this skill
Step 1 — Read the state file
Read _aibos/state-file-organization.md from the user's workspace. Three cases:
- Doesn't exist → User starting fresh. Create it from
templates/state-file-organization.template.md. Run Phase 0 (Welcome).
- Exists,
current_phase: <N> → User resuming. Load phases/0N-*.md and run that phase.
- Exists,
file_organization_complete: true → User finished initial install. Confirm completion. Offer to walk _review/ backlog or check calibration progress.
Step 2 — Verify Project 01 baseline
Before Phase 0, confirm _aibos/state.md exists and shows install_complete: true. If not, STOP and tell the user to run /onboard first.
Confirm the plugin is at v0.7.0+. The presence of skills/tidy-downloads/SKILL.md in the plugin folder confirms v0.7.0+. If missing on Mac, instruct them to download the latest cowork-ai-os.zip from https://github.com/AutomatedMarketer/cowork-ai-os/releases/latest and re-upload via Settings → Customize → Browse plugins. On Windows, instruct them to run /plugin update cowork-ai-os.
Step 3 — Run the phase script
Each phase script in phases/0N-*.md is the source of truth for that phase. Follow it exactly. Do not improvise. Do not skip questions. Do not advance until the verification at the end of the phase passes.
Step 4 — Sample-first option
At Phase 1 (declaring safe zones), offer to show the user a sample safe-zones.md first. Read from samples/safe-zones-sample.md.
Step 5 — Pause and resume
If the user types pause onboarding: save state. Tell them: "Phase X complete. You're [N]% through Project 03. Resume any time with /onboard-file-organization."
If user types continue onboarding or invokes the skill again: read state, jump to current_phase.
Step 6 — Phase completion
After verification passes for each phase:
- Update state file:
current_phase: N+1, append timestamped log entry
- Tell user: "Phase N complete. You're [%] through. [One-sentence preview of next phase]. Type
continue onboarding when ready."
Step 7 — Final phase
After Phase 4 verification passes:
- Set
file_organization_complete: true
- Set
completed_at: <ISO timestamp>
- Tell the user: "Project 03 install complete. The first weekly tidy fires [day] [time]. Walk back in 4 weeks for the calibration check, or run
/onboard-file-organization any time to resume / extend."
The five phases at a glance
| Phase | What it does | Time |
|---|
| 0 — Welcome | Greet, verify P01 + plugin v0.7.0, scaffold projects/file-organization/, create state file | ~5 min |
| 1 — Declare Safe Zones | Interview the user, write safe-zones.md (allow-list, forbidden list, "never delete" quote, STOP rule) | ~15 min |
| 2 — Verify Skill + Dry-Run | Confirm /tidy-downloads is installed, surface the verbatim safety constraints, dry-run on _test-tidy/ (refusal test + plan-then-REJECT test) | ~20 min |
| 3 — First Live Tidy | Run /tidy-downloads on real Downloads. Read the plan like a contract. Execute approved rows. Verify before/after counts. Walk _review/. | ~25 min |
| 4 — Schedule Weekly | Wire weekly scheduled tidy (PLAN only), monthly _review/ audit, calibration log, notification flow. Test the schedule with a 10-minute test run. | ~20 min |
Cross-skill dependencies
- This skill expects
/tidy-downloads to exist in the plugin install. It does not build it from scratch — it only configures safe-zones.md and verifies the shipped skill works.
- The state file at
_aibos/state-file-organization.md is separate from the Project 01 state file (_aibos/state.md) and the Project 02 state file (_aibos/state-daily-brief.md). Each project has its own state.
- The
projects/file-organization/memory.md log is the audit trail. Every weekly tidy appends a receipt. Read it before suggesting changes — historical patterns matter.
What this skill never does
- Bypass the plan-then-approve flow at any phase
- Encourage the user to "Always Allow" file-move actions
- Suggest auto-execute on scheduled runs
- Recommend any tool that deletes files
- Build a
/tidy-X variant that doesn't read safe-zones.md first
If asked to do any of the above, refuse and explain which rule it violates.
