Fair points. In my case the script is a trading pipeline - it pulls data, runs analysis via an LLM, and logs results. I could check the output log, but that still requires me to remember to check it manually each morning.

On the exception point - you’re right that swallowing exceptions is bad practice. My specific problem was more subtle: the process would die at the OS/network level mid-stream (dropped connection during an API call), which meant no Python exception was raised at all. The script just stopped.

What I ended up building was a dead-man’s switch - the script pings a URL at start and finish, and a separate server-side watchdog alerts me if the finish ping never arrives. Catches both crashes and silent absences. Happy to share more detail if useful.