I had a user ask us to solve her problems slower because it made her feel stupid when we solved them immediately.

Not tech support, but in tech, a software team with a bunch of naive Indian expats named one of the software sprints "mandigo" after Django Unchained. Only me and and Northern Irishman got it and we laughed our asses off.

Before I was officially in tech support but I was the unofficial helper in my office. I don't recall the exact issue this person was having on their desktop but I went over to help and said "have you tried restarting?" This person, a millennial, probably younger or the same age as me, then pressed the power button on the monitor to "restart". I'm still reeling.

I had changed into scrubs, booties and hair cover to go into an operating theatre and repair a printer. I didn't want to have to come out and do all that again if someone had forgotten to charge the electric screwdriver, so I revved it a couple of times while standing in the charge room, which was fully visible from the hallway. A passer-by glanced my way at the noise, did a double take at what might have been a surgeon testing off-the-shelf power tools before starting a procedure, and walked into a trash can. 😁