3 prompts ago the approach was fine. Then Claude decided the fix needed a refactor, and now 6 files are different and the tests are worse. You do not need to describe what to put back. Claude Code took a snapshot of your files before each prompt, and the rewind menu puts them back.
This post covers how checkpoints are taken, the menu and its 5 options, what is and is not tracked, and why git is still the real undo. The shortcut and menu are from the current docs, linked at the end. The post assumes a working install; Install Claude Code on Windows, Native and in WSL is the start if you need it.
How Checkpoints Work
Every prompt you send that starts a turn creates a checkpoint, and Claude Code keeps file snapshots for the 100 most recent in a session. Snapshots are saved with the conversation, so /rewind still works after you resume a session, until the 30 day sweep removes them with the transcript; the transcripts post covers cleanupPeriodDays, which keeps both longer.
Only files Claude changes with its own editing tools are tracked. That line matters later.
Open the Menu
Esc Esc with the prompt empty: open the rewind menu /rewind the same, as a command (aliases /checkpoint and /undo)
If the prompt has text in it, double Esc clears the text instead; it is saved to history, so Up brings it back. The menu lists every prompt you sent this session. Pick the one you want to go back to, then choose:
- Restore code and conversation: files and chat both go back to that point.
- Restore conversation: the chat rewinds, the files stay as they are now.
- Restore code: the files go back, the chat keeps everything that happened since.
- Summarize from here: compress everything after that prompt into a summary, to free context.
- Summarize up to here: compress everything before it, keeping the recent messages whole.
The 2 code options only appear when the selected checkpoint has file changes to revert. After a conversation restore, the prompt you selected is put back in the input so you can edit and resend it, which is the usual move: same ask, better wording.
Restore Code, Keep the Lesson
Restore code on its own is the option to reach for when the approach was wrong but the conversation was not. The files go back to the checkpoint, Claude still has the context of what it tried and why it failed, and your next prompt can say “the refactor was the mistake, keep the original structure and fix only the null check”. Plan mode is the other half of this: on a big change, plan first and there is less to rewind.
Summarise to Free Context
The 2 summarise options are a targeted /compact. A long debugging stretch in the middle of a session can be collapsed while the instructions before it and the work after it stay whole. Highlight a summarise option and type guidance in the add context field before pressing Enter to steer what the summary keeps. Nothing on disk changes, and the original messages stay in the transcript.
What Is Not Tracked
This is the section to read before trusting the menu with something that matters:
- Changes made by shell commands to a file Claude never edited with its tools. A
git checkout, a build that rewrites a file, a script Claude ran: not tracked. Once Claude has edited a file, later shell changes to that same file are undone with it. - Subagent edits. A subagent’s changes to files your main session had not already edited stay. The subagents post covers why they run apart.
- Your own edits in VS Code while the session was open, and edits from another Claude Code session in the same folder, unless they touch a file Claude had already edited.
- Symlinked and hard-linked files are skipped with a
Restored the code, but skipped N fileswarning. - A message you sent mid-turn has no checkpoint of its own and shows as
No code restore; select the prompt that started the turn instead.
For all of those, the undo is version control. The docs say it plainly: checkpoints are session-level recovery, not a replacement for git. Commit before a big change and git diff after it, and the rewind menu is a convenience on top of that rather than the safety net.
Other Considerations
Rewound messages can come back if you exit before sending another prompt, because the rewound state is saved with your next prompt. Send one before you close the terminal.
After /clear, the menu gains a top entry, /resume <session-id> (previous session), that takes you back to the conversation you cleared. It lasts until you exit or resume something else.
Rewind is not branch. To keep the current path and try another from an earlier point, /branch copies the session instead; the sessions post covers it.
/diff shows what Claude has changed in the working tree so far, which is the quicker check before deciding whether to rewind at all.
Frequently Asked Questions
Is /rewind the same as git reset?
No. It restores files Claude edited this session from its own snapshots, nothing more. Git covers everything else, including files only a command changed.
Why does the menu offer only Restore conversation?
No file edits were captured after that prompt. The code options appear only when there is something to revert.
Can I rewind after resuming a session?
Yes, checkpoints are saved with the conversation. If the snapshots have been swept, after 30 days by default, the restore fails with No files were restored.
Does rewinding cost tokens?
No. Restoring is local. A summarise option sends a request to produce the summary, like /compact does.
Esc twice opens nothing.
The prompt had text in it, so the first double Esc cleared the draft. Press it again on the empty prompt, or type /rewind.
Related
- Claude Code on Windows: The Complete Guide
- Install Claude Code on Windows, Native and in WSL
- Resume a Claude Code Session With –continue and –resume
- Plan Mode in Claude Code: Read First, Edit After
- Claude Code Subagents: Keep the Noise Out of Your Main Session
- Claude Code Only Keeps 30 Days of Transcripts
- Claude Code docs: checkpointing
- Claude Code docs: interactive mode and keyboard shortcuts
If SQL Server is part of your day job, my current work lives over at sqldba.blog: production DBA scripts, an error library and the SSMS guide.
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