Is it possible that rewind also starts a claude session and rewinds it to the conversation up to that checkpoint?

[dipree]

Originally posted by @suyashkumar2409 on Feb 11, 2026 in Discussion #258 (Ideas)

Rewind restores the codebase to a particular checkpoint, and we already have conversation history. is it possible to add a feature that can also initiate a claude session for the user with the conversation history already built in?

Even if we give a compacted summary of the conversation that has happened so far, it could be useful. Rewind would then essentially also restore the claude session along with the code at the checkpoint.

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Migrated from GitHub Discussions

[dipree]

Originally posted by @Soph on Feb 11, 2026

Maybe I'm misunderstanding but this is what entire rewind already does:

❯ entire rewind

Selected: Add a script that returns random letters
[entire] Reset shadow branch entire/e07352c-e3b0c4 to checkpoint 883ee0e
  Restored: .claude/settings.json
  Restored: .github/actions/sync-fork-checkpoints/action.yml
  Restored: .github/workflows/sync-fork-checkpoints.yml
  Restored: README.md
  Restored: random_letters.rb
  Restored: random_number.rb

Restored files from shadow commit 883ee0e

Writing transcript to: /Users/soph/.claude/projects/-Users-soph-Work-entire-test-repo/a4c21963-bb4b-4410-87fa-a67884050353.jsonl
Rewound to 883ee0e. claude -r a4c21963-bb4b-4410-87fa-a67884050353

I had a claude code session with two prompts, I exited, run entire rewind and moved one step back. Then the above output is shown. Note the last two lines, we did reset the session log to the position of that step. If you run the claude -r a4c21963-bb4b-4410-87fa-a67884050353 (with whatever random id in your case) you jump into the session at that point.

Let me know if this isn't working for you in that way.

[suyashkumar2409]

Hello, this is working fine. We can close.