There have been a few instances that I have seen where people were experiencing the same issue you are describing all the way down to the lack of entries on the calendar. After some provided logs it was determined that the controller was losing its wifi connection and hence the schedule couldn’t or wouldn’t run. If you have the ability to (temporarily) move the router or AP closer I would try that, restart the controller and see if the next schedule runs correctly. That way you can determine if thats your issue as well.