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The server's 3-way content merge was incorrectly triggering on sequential edits by the same user. When a user checked then unchecked a checklist item, the merge saw local === base (both unchecked) and kept the server's checked state, silently discarding the uncheck. Now the merge only runs when there's an actual concurrent edit (baseVersion < existing.version), meaning another user saved between the client's load and this save. For single-user sequential edits, the client's content is used directly. Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>