How to Decide When to Continue, Compact, or Restart a Claude Code Session

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Developers using Claude Code often face a choice between continuing a session, compacting context, or starting fresh when debugging stalls. The article argues there is no fixed token or message threshold — the decision should be based on observable agent behavior, such as whether it re-proposes rejected fixes or mixes unrelated tasks. Context compaction via the /compact command is recommended when the agent is on the right track but overwhelmed by noisy terminal outputs, though a structured four-question check should follow before any code edits resume. A new session is warranted when the agent loses direction, forgets rejected approaches, or conflates separate tasks like a bug fix and a README update. The author provides a decision matrix and a minimal handoff template to carry verified facts, rejected attempts, and reproduction steps into a fresh session.

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