[BUG] Desktop app (Windows): working folder no longer connects automatically in new sessions after October 2026 update that merged chat and cowork

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?

Title: [BUG] Desktop app (Windows): working folder no longer connects automatically in new sessions after October 2026 update

Summary
Until October 14, 2026, every new Cowork session in the Claude desktop app connected my working folder automatically, based on my standing instructions. After the desktop update that merged Cowork into the main Claude app, new sessions start with no folder connected. I now have to ask Claude to request access, then approve a prompt, in every session.

Environment

• OS: Windows [version]
• Claude desktop app version: [Help > About]
• Folder: C:\Users\[user]\Box\ClaudeCowork (a Box Drive folder)
• Session started from: [inside a project with the folder attached / a plain new chat]

Steps to reproduce

1. Open the Claude desktop app and start a new session.
2. Ask Claude to list the connected folder.
3. Claude reports that the computer is reachable but no folder is connected.

Expected behavior
The folder connects automatically in each new session, as it did before the update.

Actual behavior
No folder is connected. Asking Claude to request access shows a permission prompt. After approval the folder connects and can be read, but only for that one session.

Workaround
Request folder access manually at the start of each session.

Related issues

• #76187 (project folders not mounted in new sessions after an earlier update)
• #76054 (desktop bridge missing in new sessions after an update, Windows)
• #93085 (my earlier report: Box folders cannot be attached to the Linux shell)

Request
Please restore automatic folder connection for new sessions, or add a setting for a default folder that connects in every session.

What Should Happen?

The folder should connect automatically in each new session, as it did before the update.

Error Messages/Logs

N/A

Steps to Reproduce

Steps to reproduce

1. Open the Claude desktop app and start a new session.
2. Ask Claude to list the connected folder.
3. Claude reports that the computer is reachable but no folder is connected.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.37337.1 Desktop app

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

_No response_