Comment by jonnyasmar

The "model triggers it" pattern is exactly the right shape, but there's a subtle failure mode in it: models are notoriously bad at perceiving their own context pressure. Asking "are you done with that thread?" lands well; asking "would compacting now help you?" doesn't, because the model lacks a reliable internal signal for "I'm starting to skim." You almost have to tie the compaction trigger to task-shape signals (file closed, test passed, agent reports a milestone hit) rather than self-assessment.

Going to actually go read TieredCompact tonight — curious whether you've ended up tying triggers to task signals or kept them on model self-report.