I love how one of the selling points of my phone (which was all the smart "AI" crap, one of which being the ability to transcribe a recording) completely falls apart the moment it's not an American talking directly into the microphone.... I don't think it's actually understood anything I've tried to use it for, even in person and very clear discussions. But my favourites are trying to record train announcements:

"Now arriving at Berwick [Berrick]" > "now I'm riding ash ferric"

"Next [unintelligible] is Narre Warren station " > "best mattresses marijuana station"

"Berwick [Berrick]" > "Spheric"

And bonus from Sydney: "Saint Peters" became "simp penis"