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fix: use assistant turn boundaries for overflow compaction replay point#20247

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jphpeete:fix/compaction-replay-point
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fix: use assistant turn boundaries for overflow compaction replay point#20247
jphpeete wants to merge 1 commit intoanomalyco:devfrom
jphpeete:fix/compaction-replay-point

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@jphpeete jphpeete commented Mar 31, 2026

Issue for this PR

Closes #20246
Related: #19319

Type of change

  • Bug fix
  • New feature
  • Refactor / code improvement
  • Documentation

What does this PR do?

The overflow compaction replay-point search walks backward looking for role === "user" messages to decide where to split the conversation for summarization. In sessions where the user interacts through tool responses (e.g. the question tool), user messages are rare — the search skips all assistant turns and lands on the first user message, so messages.slice(0, i) produces an empty or tiny array and the summary only covers the start of the session.

This adds a check for finished assistant turns before the existing user-message check. When a finished assistant is found first, its parent user message becomes the replay point and the summary includes everything up to that assistant turn. The user-message check remains as a fallback for normal conversations.

This is a targeted fix for compaction; #19319 tracks the broader issue of synthetic user messages being treated as real user history.

How did you verify your code works?

  • bun typecheck — clean
  • bun test test/session/compaction.test.ts — 38 pass (2 new), 0 fail
  • Existing "replays the prior user turn" test passes unchanged
  • Traced through multiple scenarios: single user msg + many assistant turns, multiple user msgs with assistant turns between them, no assistant turns between user msgs

Screenshots / recordings

Not a UI change.

Checklist

  • I have tested my changes locally
  • I have not included unrelated changes in this PR

The overflow compaction replay-point search only considered user messages
when deciding where to split the conversation for summarization. In
sessions where the user interacts primarily through tool responses (e.g.
the question tool), user messages are rare and the backward walk would
skip over all assistant turns, producing an incomplete summary.

Add an assistant-turn boundary check before the user-message check. When
a finished assistant message is found, its parent user message is used as
the replay point and the summary includes all messages up to and
including that assistant turn.

Fixes anomalyco#20246
@github-actions github-actions bot added needs:compliance This means the issue will auto-close after 2 hours. and removed needs:compliance This means the issue will auto-close after 2 hours. labels Mar 31, 2026
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Thanks for updating your PR! It now meets our contributing guidelines. 👍

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Overflow compaction produces incomplete summaries in tool-heavy sessions

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