[BUG] WorkspaceTrustError: trust dialog never appears in desktop app Code tab, blocking all sessions

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?

When I try to start any session in the desktop app's Code tab, I immediately get this error:

WorkspaceTrustError: Workspace requires trust approval before starting a session.

The trust approval dialog never appears in the UI, so there is no way to grant trust. This blocks all use of the Code tab — every folder I try (existing folders, brand new empty folders, different drives) gives the same error. The dialog simply never renders.

This is the desktop app on Mac (Claude.app, Code tab), not the CLI.

What Should Happen?

A trust dialog should appear when starting a session in a new folder, asking "Do you trust the files in this folder?" with Yes/No options. After clicking Yes, the session should start normally and the trust decision should be remembered for that folder.

Error Messages/Logs

WorkspaceTrustError: Workspace requires trust approval before starting a session.

Steps to Reproduce

1. Open Claude desktop app on Mac
2. Click the "Code" tab at the top
3. Click "+ New session" in the left sidebar
4. Click "Select folder..." at the bottom and choose any folder (I tried multiple: ~/Documents/Catherine Assets, a brand new empty folder on Desktop, etc.)
5. Type any message (e.g., "hello") in the message box
6. Press Enter

Result: Error appears immediately. WorkspaceTrustError: Workspace requires trust approval before starting a session. The trust dialog never appears at any point in this flow.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.8555.2 (Claude desktop app, Code tab — not CLI)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

IMPORTANT: This bug is in the Claude desktop app's Code tab, NOT the CLI. Most existing trust-related issues and standard troubleshooting docs reference the CLI version, which behaves differently.

Troubleshooting Already Completed (none resolved the issue)

1. Updated Claude to v1.8555.2 via in-app update button
2. Quit app fully (Cmd+Q) and reopened multiple times
3. Signed out and signed back in
4. Tried multiple folders:

• ~/Documents/Catherine Assets (existing folder with content)
• Brand new empty folders created on Desktop ("claude test", "claude workspace")
• Selecting via "Open folder..." picker

1. Reset config files via Terminal:

• mv ~/.claude.json ~/claude-backup.json
• mv ~/.claude ~/claude-folder-backup

1. Full clean reinstall:

• Deleted Claude.app from /Applications
• Emptied Trash
• rm -rf ~/Library/Application\ Support/Claude
• rm -rf ~/Library/Caches/Claude
• rm -rf ~/Library/Preferences/com.anthropic.claude*
• Downloaded fresh installer from claude.ai/download
• Signed in fresh

1. Unlocked Keychain: security unlock-keychain ~/Library/Keychains/login.keychain-db

The trust dialog still never appears after any of these steps. Error is instant on any folder.

Support Ticket

Already opened with Anthropic support. The Fin AI Agent provided only CLI-specific troubleshooting that doesn't apply to the desktop app.

Account

Plan: Max
Email: dikshaa.singhal@gmail.com

Screenshot of the error attached.

<img width="1568" height="464" alt="Image" src="https://github.com/user-attachments/assets/89cbee77-2a29-49b2-9d23-24ccd036d3b6" />