Markos, Here's what I learned.
HQ has a ability to monitor anything that runs as a Windows service, but we don't have explicit support for monitoring a Scheduled Task, which is a different beast. One suggestion was: "maybe the Windows event log can be scraped to look for a success or failure event related to the scheduled task. then configure an alert based on finding the matching log event." However, not having tried this, I have no idea what pitfalls might exist with this approach.
The general consensus among those I consulted was your need would best by satisfied by a new feature, explicitly designed to monitor scheduled tasks. I've passed this on to Product Management. Would be good to hear from other folks about the value of such a feature.
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