[BUG] Desktop/Cowork: choosing "How does this work?" in the "Enable hot reloading for this session?" question just shows the same question again

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?

In a Cowork session in the Claude desktop app, Claude writes a mod into the session's dev-mods folder and the app asks "Enable hot reloading for this session?" with three options: "How does this work?", "Enable for this session" and "Not now".

Choosing "How does this work?" shows no explanation. The same three-option question appears again, every time it is chosen. The only way past it is "Enable for this session"; after that the mod loads and works.

What Should Happen?

"How does this work?" should explain what hot reloading does, then offer the same choice again.

Error Messages/Logs

None shown.

Steps to Reproduce

1. Open a Cowork session in the Claude desktop app on Windows.
2. Ask Claude to make a mod, for example one that shows context window usage. Claude loads the plugin-authoring skill and writes the mod files into the session's dev-mods folder.
3. The question "Enable hot reloading for this session?" appears with "How does this work?", "Enable for this session" and "Not now".
4. Choose "How does this work?".
5. The same question appears again with no explanation. Repeating step 4 gives the same result.

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.1.300 (Claude Code)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

Claude desktop app on Windows, Cowork session running in the cloud. The question appeared when the plugin-authoring skill wrote a mod into the session's dev-mods folder. Choosing "Enable for this session" works as a workaround.