[BUG] Cowork archive uploads (zip etc.) fail to persist to VM — docx and other regular files work fine

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 uploading archive files (e.g. .zip) through the chat attachment interface in Cowork mode, the files appear in the conversation messages but are NOT actually written to the VM's /uploads/ directory. This means the AI agent cannot access or process uploaded archives.

What Should Happen?

Uploaded archives should be correctly written to the /uploads/ directory just like regular documents (e.g. .docx). The AI agent should be able to access and extract the contents of uploaded archive files.

Error Messages/Logs

VM terminal diagnostic output:
# 1. uploads directory is empty
$ ls -la /sessions/.../mnt/uploads/
total 4
dr-x------  ... .
drwxr-xr-x  ... ..

# 2. Attempt to write a test file
$ touch /sessions/.../mnt/uploads/test.txt
touch: cannot touch '/sessions/.../mnt/uploads/test.txt': Read-only file system

# 3. Compare with outputs directory (works correctly)
$ stat /sessions/.../mnt/outputs/ --format="%A"
drwx------

$ stat /sessions/.../mnt/uploads/ --format="%A"
dr-x------

Steps to Reproduce

Open Claude Desktop in Cowork mode
Click the attachment/upload button next to the chat input
Select a .zip archive file and upload it
Ask the AI to access and process the file from /uploads/
Observe that the AI cannot find the file in /uploads/

Note: Following the same steps with a .docx or other regular document file works correctly — the file is written to /uploads/ and accessible to the AI.

Claude Model

Other

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude 1.11187.1 (370d3b) 2026-06-04T17:30:35.000Z

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

_No response_