[BUG] Personal skill not auto-triggering despite matching task description

Preflight Checklist

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

What's Wrong?

Personal skills configured in the Claude desktop app do not automatically trigger when using Claude Code, even when the skill is enabled and the task clearly matches the skill's description. The skill is visible in the Skills list and toggled on, but Claude Code generates output without applying the skill's instructions.

What Should Happen?

When a personal skill's description matches the user's task (e.g., a skill for "generating any UI code, HTML, CSS, components, webpages, or frontend designs" when asked to create an HTML file), the skill should automatically apply its instructions to the output.

Error Messages/Logs

No error messages. The skill is silently ignored.

Steps to Reproduce

1. Create a personal skill (SKILL.md) with a description targeting UI/frontend tasks
2. Confirm the skill appears in the Skills list in the desktop app
3. Toggle the skill ON
4. Open Claude Code through the desktop app
5. Ask: "create a html that has a home loan repayment calculator"
6. Observe that the generated HTML uses generic styling instead of the skill's design system

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

1.1.1520

Platform

Other

Operating System

macOS

Terminal/Shell

Other

Additional Information

Skill frontmatter description:

description: "This skill should be used whenever generating any UI code, HTML, CSS, components, webpages, or frontend designs. It provides the official design system including colors, typography, spacing, components, and Tailwind CSS classes. Always apply this skill for tasks involving: creating webpages, HTML files, UI components, forms, buttons, cards, styling, CSS, frontend code, React components, design mockups, or any visual interface work."