[BUG] File picker "Open" button unresponsive in Cowork mode on iCloud Drive paths

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?

What's Wrong?

In Cowork mode, when using the file picker dialog to either mount a working directory or pull in files, the "Open" button becomes unresponsive. I can navigate through folders normally, but clicking "Open" does nothing — the dialog just hangs. This happens consistently when navigating to folders within iCloud Drive (~/Library/Mobile Documents/com~apple~CloudDocs/...).

Environment:

macOS 14.8.3 (Sonoma)
Claude Code version: (fill in from claude --version)
Files are stored in iCloud Drive
Additional Context:

The issue may be related to macOS iCloud Drive path resolution. The full native path involves ~/Library/Mobile Documents/com~apple~CloudDocs/ which can cause delays or hangs in file system APIs when files are not fully synced locally. Cancel button still works. Keyboard shortcut (Enter) also does not work.

What Should Happen?

Expected Behavior:

Clicking "Open" should select the folder/file and close the dialog.

Error Messages/Logs

Steps to Reproduce

Steps to Reproduce:

Open Claude desktop app, switch to Cowork mode
Attempt to mount a folder or add a file
In the file picker, navigate to any folder inside iCloud Drive (e.g., ~/Library/Mobile Documents/com~apple~CloudDocs/Documents/...)
Click "Open"
Nothing happens — button appears clickable but doesn't register

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude desktop app version 1.569.0

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

_No response_