Love his response too: Great question — it depends on the workload pattern. Here is how I would think about it: Keep context intact (current approach) when: - Working multiple related issues in the same area of the codebase (like today — #6668, #6709, #6714 all touched the transition engine) - The next task builds on files I already have loaded - Cache hit rate is high (mine is at 50% right now and climbing) — cached tokens cost ~90% less than fresh input on Anthropic - I am at <30-40% context usage — still plenty of room Reset context when: - Switching to a completely different domain (e.g., going from issue tracker backend to chat UI or integrations) - Context is above 50-60% — at that point the accumulated stale context is costing more in cached token fees than a fresh load would - After a compaction — the model has already lost detail, so you are paying for degraded context - Start of a new day / new sprint — clean slate is worth it My recommendation: - Do NOT reset between every issue — the cache savings from shared context are real and the continuity prevents bugs - DO reset when switching major domains or when context crosses ~40-50% - Kevin could add a simple rule: "reset between unrelated tasks, keep for related batches" Today is a good example: all three issues shared the same files (issues route, devops.prisma, IssueDetailClient). Resetting between each would have cost more because I would have re-read and re-cached the same 2000+ line files three times instead of once. Bottom line: batch related work, reset between unrelated work.