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The automation watermarks made each nudge one-shot: fired against a failing sha (or a comment count) exactly once, with no retry if the agent was stopped when the prompt landed or the send never took — leaving red CI and open comments with no agent working and no way to re-trigger short of unchecking and re-checking. Two escapes: while a condition persists (CI still failing / comments still open) and NO turn is running in the chat, the armed automation re-nudges after a 15-minute cooldown (timestamps join the stored watermarks); and each automation row shows a "Run now" button whenever its condition is active and the agent is idle, which fires the same prompt immediately, watermarks aside. Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>