Problem (one or two sentences)

Context compression is a fairly critical step, which can be done automatically, among other things. Reversing this process requires losing a few messages.

Context (who is affected and when)

This affects those who don't want to waste time and effort rolling back and losing some of their most recent messages. It's much easier to create a checkpoint right before the compression.

Desired behavior (conceptual, not technical)

Before any context compression (manual or automatic), create a checkpoint.

Constraints / preferences (optional)

No response

Request checklist

• I've searched existing Issues and Discussions for duplicates
• This describes a specific problem with clear context and impact

Roo Code Task Links (optional)

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Acceptance criteria (optional)

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Proposed approach (optional)

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Trade-offs / risks (optional)

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