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reacechalmers
910ac4e326
The usage-based compaction gate is post-hoc: it can only see the context after a call returns and reports its counters. Between that measurement and the next request the session can grow enormously - a reasoning model emitting a long thinking block, then a tool result carrying a large file. Observed live: a call measured at 17,858 prompt tokens generated 10,842 more, a read_file added ~19k on top, and the next request reached the provider at 47,755 tokens and was rejected outright. No tuning of the post-hoc threshold prevents that, because nothing measures the session in between. Add a pre-send check driven by estimate_session_tokens, a local heuristic over the transcript, so it costs no API call and works before any usage has been recorded at all. Note the limit of this: compaction preserves the 4 most recent messages, and in an agentic tool-use loop those messages ARE the tool results carrying the bulk. This check bounds gradual growth; it cannot rescue a session whose last four messages already exceed the window. Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com> Claude-Session: https://claude.ai/code/session_013bVvRYn7CQKR6hT2j1L6Cs (cherry picked from commit 26ab52d70fb17e49b74d523aecfc1da7f69a6d60)