cowork skils bug

[cruth123-art]

Preflight Checklist

• I have searched existing issues and this hasn't been reported yet
• This is a single bug report (please file separate reports for different bugs)
• I am using the latest version of Claude Code

What's Wrong?

Bug-Report-Skills-Not-Loading.md

Bug Report: User-Created Skills Not Loading in Cowork Mode

Summary

36 user-created skills are registered in the .skills/manifest.json with valid skillId entries and "enabled": true, but none appear in the runtime available skills list, the Settings > Capabilities UI, or are invocable by name in any session. Only plugin skills (finance, legal, sales, productivity) and built-in skills load. The upload endpoint also returns HTTP 500 when attempting to add new skills through the UI.

Environment

• Platform: Windows
• App Version: Claude Desktop (Cowork mode)
• Plan: Paid (Pro/Team)
• Number of affected skills: 36 user-created skills
• Date first noticed: February 16, 2026

Steps to Reproduce

1. Open Claude Desktop in Cowork mode with a mounted workspace folder
2. Go to Settings > Capabilities > Skills
3. Observe "No skills yet. Add a skill to get started." despite 36 registered skills
4. Attempt to invoke any user-created skill by name (e.g., "run cb-monday-audit") — skill is not found
5. Attempt to upload a new .skill file via the "Add a skill" button — returns "Internal server error"

Expected Behavior

• All 36 skills in manifest.json should appear in Settings > Capabilities
• All skills should be invocable by name in any session
• The upload endpoint should accept valid .skill files

Actual Behavior

1. Settings > Capabilities shows "No skills yet" — despite 36 skills in manifest
2. Runtime skill list omits all user-created skills — only plugin skills and built-ins appear
3. Skills not invocable by name — requesting "run cb-monday-audit" returns skill not found
4. Upload endpoint returns 500 — attempting to add a new .skill file fails with Internal Server Error
5. .skills/skills/ directory intermittently empty — directory contents disappear mid-session (mount instability), though they were present at session start

Manifest Evidence

The manifest.json contains all 36 skills with valid entries, for example:

{
  "skillId": "skill_01K6hdnxciQch9Nv3nhcRy6E",
  "name": "cb-ltc-activity-codes",
  "description": "LTC activity codes audit...",
  "creatorType": "user",
  "updatedAt": "2026-02-16T12:27:22.924266Z",
  "enabled": true
}

All 36 entries follow this pattern with unique skillIds, "creatorType": "user", and "enabled": true.

Session Evidence

• At session start: ls .skills/skills/ showed 10 skill folders on disk
• Mid-session: same directory returned empty (only . and ..)
• Manifest was readable early in session, then FileNotFoundError later
• Plugin skills (finance, legal, sales, etc.) load and function normally throughout

Possibly Related Issues

• [BUG] Claude Cowork for Windows, plugin skills searched at wrong location #24859 — Cowork Windows path resolution bug for plugin skills (wrong directory traversal)
• [BUG] User-provided skills in ~/.claude/skills/ not appearing in /skills command output #14733 — User-provided skills not appearing in /skills command output
• [BUG] Claude agent in VSCODE unable to discover skills #25548 — Claude agent unable to discover skills in .claude/skills/ directory
• [BUG] Claude Code assistant not aware of available skills in .claude/skills/ directory #9716 — Claude Code skills not recognised in .claude/skills/

Impact

This is a complete failure of the user skills system in Cowork mode on Windows. No user-created skills can be discovered, loaded, or executed through the normal skill invocation pathway. The only workaround is manually reading SKILL.md files from disk during a conversation — which also fails when the mount becomes unstable mid-session.

The user has invested significant time building 36 custom operations skills for daily business use. The skills pipeline regression makes the entire custom skills feature non-functional.

Workaround

None reliable. Reading SKILL.md files directly from .skills/skills/ works only when the directory mount is stable, which is intermittent.

What Should Happen?

see pasted text

Error Messages/Logs

see pasted text

Steps to Reproduce

see pasted text

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

No response

Claude Code Version

latest

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

No response

[github-actions]

Found 3 possible duplicate issues:

1. [BUG] Cowork: request_cowork_directory tool missing from session runtime after latest desktop app update - folder mounting broken #25797
2. [BUG] Skills not loading from ~/.claude/skills/ directory #25072
3. Skills not loading: ENOENT error on managed skills directory aborts user skills loading #20576

This issue will be automatically closed as a duplicate in 3 days.

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🤖 Generated with Claude Code

[francisco-perez-sorrosal]

I have the same problem in Claude Desktop. Trying to upload (for update purposes) a couple of zipped skills that I could upload without problems and were working minutes before, now show the behavior described in 4. Upload endpoint returns 500 — attempting to add a new .skill file fails with Internal Server Error

[raidhosn]

I get the following error when trying to upload a Claude skill.

Upload skill

x

4

Internal server error

Drag and drop or click to upload

File requirements
. .md file must contain skill name and description formatted in YAML
. .zip or .skill file must include a SKILL.md file

Read more about creating skills or see an example

[IamGittingHub]

Experiencing the same issue on claude.ai (Pro plan, browser).

I have 46 custom skills uploaded. 26 of them load and sync to disk normally — their SKILL.md files and reference folders are accessible at /mnt/skills/user/ during conversations. The other 20 are registered in the system (their names, descriptions, and trigger patterns appear in the available_skills list), but their actual files never sync to the /mnt/skills/user/ directory. When Claude tries to read them with the view tool, the paths don't exist.

The 20 broken skills were uploaded at a similar time and all show the same behavior — metadata visible, files missing. The 26 working skills were uploaded earlier and function perfectly.

This is blocking a significant part of my workflow. These are production skills I use daily for my business (copywriting, email sequences, content strategy, marketing psychology, etc.).

Environment:

• Platform: claude.ai (browser)
• Plan: Pro
• OS: Windows
• Skills affected: 20 out of 46 custom skills
• Behavior: Skill metadata/descriptions load into context, but SKILL.md files are not present on the filesystem mount during conversations

[jvsteiner]

i published a skill, and them updated it, incrementing the version. I also installed it in claude code (desktop) (it works in both). after updating, the version incremented in code, but not in cowork (again desktop). its like the cache is stuck. could be related.

[francisco-perez-sorrosal]

Seems to be solved now. Drag and drop the skills work again and execute without problems

[jvsteiner]

Seems to be solved now. Drag and drop the skills work again and execute without problems

not sure what you mean by drag and drop - I installed from github - I think you need to use the update button for skills installed that way.

[castamos-auto]

I'm experiencing the same issue, I can upload new skills through the web interface, and apparently they are added, Claude can even detect them (it can read the skill names/descriptions) but when it actually attempts to load the skill files (Skill.md) it fails to find them.

I uploaded a skill on Feb/10 and that one is working fine, but the skills I uploaded since Feb/17 are unusable.