I’ve been running Claude Code most days for a few months and I still don’t have a principled answer for this. My current rule is vibes: when it starts re-reading files it already read, or repeats a fix I rejected two turns ago, I bail and start over with a summary. Compaction helps but the session is usually already degraded by the time it kicks in, so I’ve started doing it manually way earlier than I need to. What I can’t work out is whether a long session is genuinely worse, or whether I’ve just trained myself to blame the session when the task was underspecified from the start. Curious what other people use as the trigger. Token count? Number of tool calls? Something concrete, or also vibes? submitted by /u/ronin4001
Originally posted by u/ronin4001 on r/ClaudeCode