Not a dev job but one I quit.

The company had Windows 98 on all their computers and we had to use it for our daily activities. Being relatively young, I'd only used Windows 98 for a couple of years between the age of 5 and 8 and mostly for playing games.

The company was paying me overtime to stay late and familiarise with the OS.

Basically, they were willing to spend money to train employees to use an obsolete OS - what a bunch of idiots and poor decision-makers.

I left after three months because I could no longer cope with their nonsense.