I will admit it was not my kindest joke, but on the other hand, I genuinely did not expect him to read a treatise on IOT infrastructure.

I think you have some leeway joking on a guy who wrote a song called "Let's get retarded"

Was genuinely my feeling at the time, too.

A selling point for humans is that some of them are actually funny, unlike LLMs which just regurgitate synatically competent but humourously incompetent waffle.

I dunno. The latter part sounds like a number of humans I've interacted with. They're all nice people though.