Will do a feedback because this functionality is definitely seriously broken. In the meantime to recreate the bug:
1/ in Automator generate an App containing just one action "Run Apple Script" where the script contains:
set CurrentDate to (date string of (current date))
set CurrentTime to (time string of (current date))
set atab to " "
set f to "~/Documents/Stamp.log"
set lineToAppend to CurrentDate & (quoted form of atab) & CurrentTime
do shell script "echo " & atab & lineToAppend & " >> " & f
2/ Save that App somewhere and call it "Stamp"".
3/ in Calendar generate an Event to start tomorrow sometimes in the morning say 7 am with an alert "Open a file at time of event" and select an App from the previous step as a file to open. Set the event to repeat every day.
4/ duplicate that event and change its start to the same day but say 1 pm. Set to repeat every day. You should have now two new events repeating everyday at 7am and 1pm.
5/ the next day the system will request to grant the app "Stamp" access to your Documents folder. Grant it.
6/ sometimes after 3pm that day go and open the log file called Stamp.log in your Documents folder.
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Here is what I see in the log, original as scheduled executions each followed by another one some 20 minutes later.
Saturday, July 23, 2022 7:00:01 AM
Saturday, July 23, 2022 7:23:03 AM
Saturday, July 23, 2022 1:00:00 PM
Saturday, July 23, 2022 1:21:43 PM
Apple FIX IT PLEASE.
