Free Claude Cowork Skill
Keep your Cowork workspace from quietly falling apart.
Cowork System Health Check Deluxe is a free skill that audits your entire Claude workspace in one pass — finds drift, bloat, broken references, and misplaced rules before they compound into bad output.
Download the skill — it’s free.skill file · works with Claude Cowork
The problem it solves
A Cowork workspace is a living system. Rules drift into the wrong files. MEMORY.md fills up. Hub tables fall out of sync with your Routing Map. Reference pointers break when files get renamed. None of these problems announce themselves — they just quietly degrade your output until sessions start feeling off and you can’t pinpoint why.
I built this skill because I kept running into exactly that. What I needed was something that would read the whole workspace systematically, tell me exactly what was wrong, and wait for my approval before touching anything. This is that.
What it checks
- Root CLAUDE.md bloat and line count
- Root MEMORY.md ceiling and stale entries
- Hub files — present, lean, no duplicates
- Hub list vs. Routing Map sync
- References section — both directions
- Orphaned files at the workspace root
- Precision checklist — 20+ specific items
- Self-learning loop gaps
- Correction log freshness
- Automation and session-close gaps
It delivers a 🟢/🟡/🔴 dashboard for every area of your workspace — so you get a health picture at a glance, not just a list of complaints.
How it works
- DiscoverRuns bash to map your workspace structure and get quantitative line counts before reading anything.
- Read everythingReads root files, all hub files, and your Resources folder in session-startup order.
- CritiqueEvaluates findings against Boris Cherny (self-improving systems) and Jeff Su (token economy) principles. Runs a 20+ item precision checklist and three cross-file integrity checks.
- Gap reportPresents a structured dashboard with every finding, its severity, the framework it violates, and the exact proposed fix. Nothing changes yet.
- Implement — with your approvalYou approve all, some, or none of the proposed fixes. Changes execute one file at a time, with a read-back verification after each one.
- VerifyRe-runs the precision checklist to confirm every failing item now passes. Walks the session-open sequence end-to-end.
- Audit trailAppends a dated entry to MEMORY.md recording what changed and why. Logs any new patterns to the correction log.
Works for any Cowork setup
The skill discovers your workspace structure dynamically — it doesn’t assume a specific number of hubs, specific file names, or a particular layout. Whether you have three hubs or ten, whether you call your correction log “lessons.md” or something else, it adapts. First-time users get a gentle pass; the skill distinguishes “missing because it hasn’t been built yet” from “missing because it drifted.”
Requirements
- Claude Cowork (desktop app)
- A Claude Home folder with at least a root CLAUDE.md and MEMORY.md
- That’s it
How to install
Download the .skill file below, then open Claude Cowork and click Save Skill when prompted. The skill appears in your available skills list immediately. Trigger it anytime by saying “run a health check” or “audit my Cowork files.”
Download cowork-system-health-check-deluxe
Built by Steve Goodman. Free to use, share, and adapt. If it improves your workflow, I’d love to hear about it.
No tracking. No email required. Just a skill that does what it says.