The Misunderstandings
"Hey assistant, set an alarm for 7 AM." "Okay, setting alarm for... 7 PM." THAT'S NOT WHAT I SAID. I said AM. AM!
I've given up. I set alarms manually now like some kind of caveperson. It's slower but at least it works.
The Embarrassment
Other people are around and my assistant "accidentally" hears them and does something weird. "Playing 'Baby Shark' on repeat!" NO I DIDN'T ASK FOR THAT. The shame.