[BUG] Claude Desktop Cowork Authentication Infinite Loop

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?

Environment:

• Claude Desktop version: 1.3883.0 (93ff6c)
• Operating System: macOS
• Account Type: Enterprise (Zillow Group)

Issue Summary:
Cowork mode authentication hangs indefinitely with spinning authentication icon, eventually freezing the entire Claude Desktop application including Chat mode. Force quit required to exit.

Steps to Reproduce:

• Open Claude Desktop
• Attempt to access Cowork mode
• Authentication spinner appears and runs indefinitely
• After some time, entire application becomes unresponsive
• Chat mode also becomes inaccessible

Actual Behavior:

• Authentication never completes
• Spinning authentication icon continues indefinitely
• Entire application freezes, requiring force quit
• Chat mode works normally until Cowork authentication is attempted

Troubleshooting Attempted:

• Complete app data reset via Help > Troubleshooting > Reset App Data
• Full logout/login via Claude Code CLI
• System restart
• Verified system clock accuracy
• Updated to latest desktop version

Additional Notes:
Chat mode functions normally until Cowork authentication is attempted. Issue appears related to enterprise SSO configuration differences between Chat and Cowork authentication flows.

What Should Happen?

Expected Behavior:

• Cowork authentication should complete successfully, allowing access to collaborative features.
• ENtire desktop app should not freeze when Cowork is asked a question

Error Messages/Logs

NOne.  Just see an eternal Authenticating... with the claude icon flashing

Steps to Reproduce

1. Open desktop app
2. Prompt for ANYTHING in cowork
3. Authenticating forever... app freezes

Claude Model

Not sure / Multiple models

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

Version 1.3883.0 (93ff6c)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_