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Agreed. And while I’m sure we have all been let down by apps/tech at one point or another, I think the user in this case discounts the tremendous effort put into developing apps, and to me a somewhat “cutesy” error message is enough to remind me that a human created the very opportunity I feel let down by.

I started a reply thinking this is probably absurd to do, but I realise it's probably possible. A/B test error messages, outcome are support tickets, app reviews. That's said I'm not sure if anyone would bother to setup tests for error messages, there probably more important things to do like fix the actual cause

Were cutesy errors backed up by usability testing?

If not then that just means that both this counterargument against cutesy errors as well as the original rationale to have them in the first place are both equally weak. That's not a point in favour of this argument.

Points in favor of this argument can be found in other comments.

OK, sure, but what does that have to do with what I'm saying about usability testing being important to validate your hypotheses?