digging around in my 2K Marin-era (2008-ish) archives and came across this outstanding error message, props to whatever IT(?) person decided to phrase a simple seat license conflict as "Human Combat Required":
@jplebreton This is beautiful. I want to write error messages this good.
@jplebreton very adventure games-esque wording there. just need to type in the 17th word on page 53 of the manual and it should unlock 
@jplebreton Don't show this to Autodesk or Adobe.

@jplebreton A friend I had in a previous workplace a few decades ago got to build a custom print server for some branch hardware. And one things printers love doing is throwing errors. So there was an error handler. He was feeling a little whimsical that day, though and one of the messages was "Orange marmalade? No! Paper jam!".

Then he promptly forgot he'd done this and never documented it. When the support desk learnt about it, from someone in the field, they were definitely amused. The only negative was they they would've liked it to have been documented. :)

@jplebreton ah, yes, they must have hired klingon intellectual property lawyers for that one
@jplebreton @lysdexic This reminded me: In retrospect, I should have known that my last job wasn't going to work out the day I got an enhancement ticket that said "please make the access token error logging less amusing"
@jplebreton "If Klingon's wrote system messages..."

@jplebreton

Ah yes, the Klingon Public License (KPL)

@jplebreton love it, injecting a bit of personality & whimsy into our interactions with The Machine
@jplebreton It has been several days now. How did the battle turn out? Who gets to own the software?
@nazokiyoubinbou it was a screenshot, so alas the battle occurred many many years ago...
@jplebreton Are you saying we will never know what the outcome was?