[BUG] rewind of code doesn't work most of the time

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 I hit double ESC and rewind the conversation with code changes, more often than not, especially when there were multi-file changes, it doesn't revert the files.

I'm using Claude Code within VS Code (Cursor technically), in the classic (cli) form, not the newer GUI.

I'm obviously not alone in experiencing this issue: https://www.reddit.com/r/ClaudeCode/comments/1pyks4r/rewind_does_not_seem_to_work_a_lot_of_the_times_i/

What Should Happen?

Files should be reverted.

Error Messages/Logs

Steps to Reproduce

Open project with many files, do some multi-file change task (while the corresponding files are also open in VS Code), try to rewind with code restoration. Code doesn't actually restore.

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.9

Platform

Anthropic API

Operating System

Ubuntu/Debian Linux

Terminal/Shell

Cursor

Additional Information

_No response_