Ok so I should not use restart then. Thanks for clearing that up!
That’s not what was suggested; Stiltjack simply clarified the meaning of mode: restart (because you had misunderstood its purpose). In this particular case, the automation’s failure to trigger isn’t due to its choice of mode. For more information, refer to: Script Modes.
So I did a test now after removing almost all my automations and setting the time to a few minutes later on the auto-restart for HA. And it worked, so there must’ve been a typo somewhere that was causing this issue. I will do some further testing but it seems like this solved it!