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Is there a way to automatically flush failed policy logs so that the policy is made available again in Self Service without an administrator having to flush the log manually?

Sounds like you're looking for this feature request: https://jamfnation.jamfsoftware.com/featureRequest.html?id=827
Or maybe you could set the policy to "ongoing"?


Bingo; for a Self Service policy, I tend to choose "Ongoing" for this very reason (or at a minimum, ongoing + target it based on group membership).