How To Trigger a Macro Once After 2pm If Another Condition Has Been Met?

That's doable.

I don't have any idle triggers, so I'm not going to take the time to pony one up.

Here's one example:

Trigger: when Mac is idle (THEN STOP) - #6 by _jims

I'd probably:

  • Use a global time-of-day triggered macro set to 2:00pm to activate an IDLE-Trigger sub-macro.

  • If the IDLE-Trigger macro activates Messenger then it disables itself and won't be activated again until the next clock cycle.

Keyboard Maestro has IDLE, Time-Of-Day, and Cron triggers amongst others: Macro Triggers user manual section.

So you have a great deal of flexibility.

-Chris