Probably my favorite experience with someone, would have to be at my previous job.
I worked with an MSP who had set up a new VDI environment with VMWare for a confidential client. About a day after it's online, I get a call from the CEO of said client. He asked where on his PC he could go to access his VDI, and insisted that i remote into his system in order to show him.
Low and behold, on his desktop was a lone shortcut with the name "%USERNAME%-VDI"
Needless to say his frustration dropped quickly after being shown where to locate his VDI.