Sir Codin
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This one simply takes the cake:
I am a system administrator, but at times, when I'm feeling benevolent, I assist technically challenged users. I was speaking with one of the network analysts while enjoying a cup of latte, when a woman from the Health Services department frantically rushed over to us. We told her to call the help desk, which is what she is supposed to do first, and then her problem would probably be assigned to one of us. She couldn't wait, though -- you know that scenario. She needed to copy a document to a disk immediately, but her disk drive was "broken." She was flailing her arms with the diskette in her hand saying, "I keep trying to put the diskette in, but it won't go in. The disk drive is broken!"
The analyst and I looked at each other, then followed her to her computer. We stood next to her as she repeated her story. At the same time, she was unsuccessfully attempting to shove her diskette into the drive...with the disk upside down.
I told her that there wasn't anything wrong with her drive. I said her computer was upside down.
...OH MY GAAAAAWWWWWDDDDD!!!!!!!
Edit: oh god hahahaha
One night there was a thunderstorm in the area, and one customer, notorious among the tech support crowd, called:
Customer: "Did you know about the thunderstorm? I heard that I should unplug my computer. Should I do that?"
Tech Support: "In most cases, yes, it is best to at least unplug your phone line. Lightning sometimes causes power surges that can damage your modem."
Customer: "Can it damage other things as well...like the phone?"
Tech Support: "I've never heard of that happening before, but it is a possibility."
Customer: "So do you think that I should unplug the phone from my computer and from all the phones as well?"
Tech Support: (frustrated) "Couldn't hurt."
Customer: "So when can I plug them all back in?"
Tech Support: (really annoyed now) "When the storm is over."
Customer: "How will I know when it's safe, though?"
My face lit up like a Christmas tree, and it was all I could do to keep myself breathing evenly.
Tech Support: "I will call you."
Customer: "Ok! Thank you!"
Okay, that one was awesome. XD