[FEATURE]

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

Rewind drops the most recent state when freeing space.

Proposed Solution

It should "rewind" or drop the oldest. Most recent state is the most important to maintain.

Alternative Solutions

There is no workaround that I have found.

Priority

High - Significant impact on productivity

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

One thing that seems to cause the need for a rewind is uploading or pasting images for Claude code to review. I have been able to get around this in some cases by dropping images into a folder and providing the local path. It would be nice if there were a way to temporarily drop images for review. In most cases I don't need it to retain the image beyond the initial inquiry.