[BUG] Claude Desktop Cowork freezes at “Authenticating” — LocalAgentModeSessions OAuth exchange never completes

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?

Claude Desktop Cowork freezes at “Authenticating…” after I send the first message.

Claude Desktop Chat works.
Claude Code CLI works.
Only Claude Desktop Cowork fails.

The issue appears isolated to Cowork local-session OAuth/provisioning. Logs show Cowork reaches LocalAgentModeSessions.start, begins a fresh OAuth exchange for the Cowork local session, but never completes the token flow.

Environment

• Claude Desktop version: 1.7196.0
• Claude Code version: native 2.1.143
• Platform: darwin-arm64
• macOS version: [paste macOS version from sw_vers]
• Plan/org: Claude Team, org name Apex Signature
• Active org in Desktop: John · Apex Signature

Steps to reproduce

1. Open Claude Desktop.
2. Confirm active org is Apex Signature.
3. Open Cowork.
4. Select a local trusted working folder.
5. Start a new task.
6. Send a simple message such as hi.
7. Cowork shows “Authenticating…” indefinitely and never starts the task.

Expected behavior

Cowork should authenticate the local session and begin the task.

Actual behavior

Cowork remains stuck at “Authenticating…” after the first message. The task never starts.

Relevant logs

The logs show:

LocalAgentModeSessions.start:
using oauth config {
  redirectUri: 'https://console.anthropic.com/oauth/code/callback',
[oauth] looking up token for orgId=...
[oauth] no cached token found for orgId=...
[oauth] performing fresh oauth exchange for orgId=...
Transcript not found for session local_... (cliSessionId: none)

### What Should Happen?

When I send the first message in Claude Desktop Cowork, Cowork should complete the local-session OAuth/authentication flow, create the Cowork session, and begin processing the task.

The task should move past “Authenticating…” and either start responding, show task progress, or display a clear error message if authentication fails.

Cowork should not hang indefinitely or require force quitting Claude Desktop.

### Error Messages/Logs

```shell
Cowork UI error/state:
Claude Desktop Cowork freezes at “Authenticating…” after I send the first message. There is no visible error message. The task never starts and Claude Desktop must be force quit.

Relevant log pattern:

LocalAgentModeSessions.start:
using oauth config {
  redirectUri: 'https://console.anthropic.com/oauth/code/callback',
}

[oauth] looking up token for orgId=[REDACTED], cacheKey=[REDACTED]
[oauth] no cached token found for orgId=[REDACTED]
[oauth] performing fresh oauth exchange for orgId=[REDACTED]

Transcript not found for session local_[REDACTED] (cliSessionId: none)

Important detail:
For the failed Cowork session attempt, there is no later successful “obtained new token” message after “performing fresh oauth exchange.” Cowork remains stuck at “Authenticating…”.

Other relevant log entries seen during testing:
- Cannot initialize sessions: accountId=null, orgId=null. Keeping existing sessions.
- No active account/org for marketplace operations.
- Coder workspace discovery failed: Error: coder CLI not found on augmented PATH.

Notes:
- Claude Desktop Chat works.
- Claude Code CLI works.
- Claude Code doctor is healthy after cleanup.
- Active Desktop org is selected as Apex Signature.
- Local working folder is trusted.
- Cowork VM download endpoint is reachable.

Steps to Reproduce

1. Open Claude Desktop on macOS.
2. Confirm the active account/org is selected: John · Apex Signature.
3. Go to the Cowork tab.
4. Start a new Cowork task.
5. Select a local trusted working folder.
6. Type a simple first message, such as hi.
7. Send the message.
8. Cowork accepts/queues the message, then shows “Authenticating…”.
9. Cowork stays stuck on “Authenticating…” indefinitely and the task never starts.
10. Claude Desktop must be force quit to recover.

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude Code version: native 2.1.143, Platform: darwin-arm64, Install method: native

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Additional context:

This issue appears isolated to Claude Desktop Cowork.

Confirmed working:

• Claude Desktop Chat works normally.
• Claude Code CLI works normally.
• Claude Code doctor is healthy.
• Active Desktop org is selected as John · Apex Signature.
• Local working folder is selected and trusted.
• Cowork VM download endpoint is reachable.

Troubleshooting already completed:

• Signed out and back in from Claude Desktop.
• Fully quit and force quit Claude Desktop.
• Reopened Claude Desktop and tested a new Cowork task.
• Selected a simple local working folder.
• Reset Claude Desktop/Cowork local app state.
• Tested with VPN off.
• Checked system time.
• Checked Keychain / ran claude doctor.
• Cleaned up duplicate Claude Code installations.
• Confirmed Claude Code is now native 2.1.143 on darwin-arm64.

The failure still happens consistently after all of the above.

Support conversation ID, if useful:
215474332134414