[BUG] Cowork: ~30-second 'Authenticating' delay on every prompt within a conversation

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 Claude Desktop's Cowork tab, every message in an ongoing conversation triggers a fresh ~30-second "Authenticating" step before the response begins. The session does eventually proceed — it is not stuck indefinitely — but the delay repeats on every single prompt without exception.

This was directly observed during an active Cowork session on April 13, 2026 involving a long technical conversation with 20+ prompts. Every prompt triggered the authenticating delay. Cumulative dead wait time across the session: approximately 10+ minutes.

The regular Chat tab in the same Claude Desktop app is completely unaffected.

What Should Happen?

Authentication should happen once per Cowork session. Subsequent messages in the same conversation should respond immediately without re-authenticating each time.

Error Messages/Logs

Steps to Reproduce

1. Open Claude Desktop
2. Click the Cowork tab
3. Start a new conversation and send any message
4. Wait for the response
5. Send a second message in the same conversation
6. Observe ~30-second "Authenticating" step before response begins
7. Repeat — delay occurs on every subsequent message without exception

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

1.1617.0

Claude Code Version

2.1.104

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This was observed during an active Cowork session on April 13, 2026 with 20+ prompts — every single one triggered the delay. Cumulative wait time: ~10 minutes across the session.

This is distinct from issue #44654 (indefinite hang). Here the session always recovers after ~30 seconds, but re-authenticates on every prompt. Root cause appears to be a missing token cache — a fresh OAuth exchange is triggered each time instead of reusing the session token.

Regular Chat tab in the same Claude Desktop app is completely unaffected.