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Why did my loop not run overnight?
Almost always the machine went to sleep, and a sleeping machine does not run scheduled jobs. Claude Desktop's Scheduled Tasks do not wake a suspended computer.
The skipped fires are silent: nothing is written anywhere to tell you why.
On macOS, check pmset -g and consider sudo pmset -c sleep 0 so the machine stays awake on power. On Linux, check whether logind suspends on lid close or idle, and set HandleLidSwitch=ignore if it does. On a headless box that never sleeps, check that both scheduled tasks are enabled.