When is a Claude Code session too long? Devs debate context rot and checkpoints
Miserable_Ground_669 · reddit · 2026-10-14
A developer describes a familiar trap: a planned 20-minute test fix with Claude Code turned into a 3-hour session touching auth, a migration, and a long-forgotten helper file. Most of it worked by the end, but the chat was full of dead ends, reverted fixes, and files Claude was told not to touch. The core dilemma: keep going (the session 'knows' everything) or restart (half the context is junk)? The author explores session-history tooling and wants checkpoint-style rollback — going back 40 minutes to before an unrelated 'quick fix' changed six files. The thread asks whether others deliberately restart sessions or ride until the model starts forgetting and misbehaving.
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