What’s the oldest example of a Digital Assistant misunderstanding something?

There was a 1966 episode of The Monkees where Peter has trouble with a voice-controlled machine:

DJ-69 : Take a seat please. To preclude the variable factor inherent in the human equation, we have instituted this new electronic personnel procedure requiring… Your name, please.
Peter : What?
DJ-69 : Thank you. Last name: What. And your first name, Mr. What?
Peter : N - It’s not ‘What’.
DJ-69 : Notwhat. Mr. Notwhat What.

(Very likely the inspiration for the “Not Sure” scene in Idiocracy.)