[FEATURE REQUEST] Register AskUserQuestion as a rewindable checkpoint (Bypassing stale loop of #18141 / #34232)

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

Description:
Currently, when Claude pauses execution to use the AskUserQuestion tool, this interaction is not saved as a checkpoint in the chat history.

The Problem:
If a user selects the wrong multiple-choice option or wants to change their answer to a tool prompt, they cannot use the Esc Esc (or /rewind) menu to roll back to that specific decision point.

Proposed Solution

Please register AskUserQuestion (and any other tools that require manual user input) as standard checkpoints. This would allow users to easily rewind to the prompt, change their answer, and branch the execution naturally.

Alternative Solutions

_No response_

Priority

High - Significant impact on productivity

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

Note on Duplicate Flags:
I am opening this new issue because the previous identical requests (#18141 and #34232) were caught in a bot loop—one was closed as a duplicate of the other, which was then closed by the stale bot without being addressed. Please keep this active so the team can review it!