I've some statically generated site being served by a simple web server.
Sometimes the batch process generating them doesn't work anymore and the pages remain non-fresh but correctly served, so for my updown check everything looks great.
I would love to have a way to specify some text with a date in the page (in a standardized way so that is easy for updown to parse it) and tell updown to fire an alarm if the date is not recent enough.
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That would be a bit too niche for the added complexity but I can recommend something else for this scenario, you can use the Pulse monitoring feature to send a pulse to updown.io at the end of your generation process, and this way updown can alert you if it has not received any pulse for more than X hours/days: https://updown.io/doc/how-pulse-cron-monitoring-works
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