My favorite error that I get on occasion:
Me: From Windows, I shut down my computer.
Windows (during shutdown): "An error has occurred, you must shut down your computer. Press OK to continue."
Me: I MUST shut down!?! That's what I was trying to do! How about just shutting the $%^$ thing down instead of interrupting the process to tell me that I need to shut down when I was already trying to do that! **&*$ #&*#, $#(*#$!!!!
(I love Windows

)