Conversation Compaction: Test What a Summary Must Preserve

Conversation compaction should be evaluated by how well it preserves the information required for a future task rather than by achieving a fixed reduction ratio. Effective handoffs vary by use case, retaining items such as decisions, constraints, unresolved questions, evidence sources, changed files, failed approaches, and remaining checks while clearly distinguishing proposals from approved actions, observations from hypotheses, and temporary instructions from durable preferences. Summaries should be tested against questions a subsequent session must answer and should preserve disagreements or uncertainty rather than creating false certainty through simplification. Practical evaluation should compare multiple summary budgets using measures such as task correctness, source recovery, repeated work, and unsupported assumptions, including tests of information loss across repeated rounds of compaction. Compact summaries can be paired with selective retrieval and separate durable records, with approaches such as Anthropic’s context-engineering guidance, few-shot context budgeting, and Supermemory serving as tools to assess rather than universal prescriptions.

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