As long as it doesn’t contravene the Apple Style Guide:
“Humor can enhance documentation by adding to a reader’s enjoyment and by helping to lighten the tone. Humor usually works best in examples, where it’s less likely to distract the reader. Be careful that your humor is in good taste—one reader’s joke can be another reader’s insult—and keep in mind that humor may not translate well in localized text.”
It blows my mind how common taking a silly tone in error messages has become. It's _exactly_ the time the user shouldn't get the impression that you're taking a haha oh well attitude.
Humor is subjective, but I've always found Craig's performative sense of humor to be more annoying than anything else. The smug brainiac shtick is so old at this point that the dude practically steps on Steve Ballmer's feet.
“Humor can enhance documentation by adding to a reader’s enjoyment and by helping to lighten the tone. Humor usually works best in examples, where it’s less likely to distract the reader. Be careful that your humor is in good taste—one reader’s joke can be another reader’s insult—and keep in mind that humor may not translate well in localized text.”
https://help.apple.com/applestyleguide/#/apsg9dac5903