I have a macro which kills "Messages" and "Outlook", then activate them after 10 seconds. It works when I try it by click "Try", but it fails to activate "Outlook" when schedule this macro to run at 7:30am everyday(the Macos is in sleep mode at this time). Messages worked ok. Macro screenshot attached. What could be the reason that "Outlook" doesn't activated?
Then something else is going on, because your Mac must be awake for a "Time of Day" trigger to fire a macro -- see the trigger's Wiki page.
So you need to make sure your Mac is awake before your macro is due to run. You may also need change the pause if Outlook takes longer to update its files and quit -- or change the pause to "Pause Until" with the condition "Microsoft Outlook is not running".
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I think that's probably the reason. It works for Messages but not for Outlook.
In fact, the screen is off, but Mac is running, because every morning I noticed the Mac is warm, not cold.