I don't think you can do this in OnDemand.
I've been doing it for years using "jelly escalation", but OnDemand doesn't support Jelly scripting or services (yet)
The best you can do is create a filter for "issues past due" and then use a subscription to get it regularly. It's a list, generated at the time the subscrition is set to run for, but it does the basics.
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