Add 'compact context' option when accepting plans in Plan Mode

[diegoesolorzano]

Problem

When accepting a plan in Plan Mode, the only context management option available is "clear context" (enabled via showClearContextOnPlanAccept). This is a binary choice: either keep the full context (with all exploration cruft) or wipe it entirely.

Clearing context loses valuable information — decisions made during exploration, constraints discovered, instructions from skills/workflows, and reasoning that informed the plan. Keeping everything wastes context window on verbose tool outputs and dead-end explorations.

Proposed Solution

Add a "compact context and implement" option to the plan acceptance prompt, alongside the existing clear/keep options. This would run the equivalent of /compact before transitioning to execution mode.

Compaction preserves the important parts (decisions, constraints, plan rationale) while removing noise (verbose tool outputs, exploration tangents, failed attempts). This gives the execution phase a clean but informed context window.

Possible implementations

1. New option in the plan accept prompt: "Yes, compact context and implement" as a third choice
2. New setting: compactOnPlanAccept: true (similar to showClearContextOnPlanAccept)
3. New hook event: PlanAccept — would let users configure any behavior at the plan→execution transition, including but not limited to compaction

Option 3 is the most flexible and consistent with the existing hooks architecture.

Current Workaround

Accept plan → manually run /compact → Claude resumes execution. Works, but adds friction to every plan cycle.

Related Issues

• Add "compact context" option when exiting plan mode + allow configuring default #19326 — Original request for compact option in plan mode
• Plan mode: 'Clear context and implement' as default is destructive and irreversible #25734 — Discussion about clear context being destructive as default
• Feature Request: Allow configuring or disabling 'clear context' default when accepting plans #18878 — Configuring/disabling clear context default

[github-actions]

Found 2 possible duplicate issues:

1. Add "compact context" option when exiting plan mode + allow configuring default #19326
2. [FEATURE] Add "Compact and auto-accept edits" option to plan mode approval dialog #26349

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[diegoesolorzano]

Please take in count this or help us on how to do it.

[robertmhaas]

Yes, this is a huge problem. Often what happens for me is that the implementation itself goes pretty OK, but then afterward Claude knows absolutely nothing any more about what we were talking about before, and so the whole conversation goes wildly off the rails. According to Claude itself, the issue is that the exploration while generating a plan produces a lot of cruft -- and it's reasonable to clear that cruft. But if we're implementing a plan to add shoelaces to our existing shoe implementation, we should not forget what shoes are just because we implemented something. It's wildly frustrating.

[qtaraki]

+1 to @robertmhaas note above

[github-actions]

Closing for now — inactive for too long. Please open a new issue if this is still relevant.

[github-actions]

This issue has been automatically locked since it was closed and has not had any activity for 7 days. If you're experiencing a similar issue, please file a new issue and reference this one if it's relevant.