Working in tech support is a bit like teaching preschool: You're an educator who provides reassurance in troubling times. You share knowledge and help others overcome their obstacles. And some days, it feels like all you hear is screaming, crying, and incoherent babble.

Tech support is no cakewalk -- there's no question about that -- but boy, does it lead to entertaining anecdotes. After all, if the IT pro is the preschool teacher, the customers are the children. And kids, as we all know, are always saying the darnedest things.

[ For more real-world tales of brain fail, see "Stupid user tricks 6: IT idiocy loves company." | Find out which of our eight classic IT personality types best suit your temperament by taking the InfoWorld IT personality type quiz. | Get a $50 American Express gift cheque if we publish your tech tale from the trenches. Send it to offtherecord@infoworld.com. ]

We've trotted through the trenches of tech support to dig up truly memorable tales of trouble and triumph. Some of the names and places have been omitted to protect the guilty, but the stories themselves are all real. Honestly, we couldn't make this stuff up if we tried.

Stupid Tech Support Trick No. 1: The Pronoun Problem

In tech support, even the most basic assumptions can backfire. Tim Crotwell, a network admin at a Mississippi school district, learned that firsthand -- and he's still laughing about his lesson years later.

Crotwell was working off-site one day when an office manager -- we'll call her Ms. Schmidt -- phoned him up with an urgent issue. Ms. Schmidt was trying to print some documents, she told him, and her printer wasn't responding.

The fix was simple enough: Crotwell just needed to talk her through clearing the Windows print queue and restarting the print job. Tech Support 101, right?

"I told her to go to My Computer and open the Printers folder," Crotwell explains.

That's when the case took an unusual turn. Ms. Schmidt told Crotwell to hold on and stayed away for a solid few minutes. When she finally came back on the line, she told Crotwell she had followed his instructions -- but saw no sign of her printer in the folder.

"I said, 'It should be there, unless you accidentally deleted it.' I walked her through refreshing the list and arranging the printers by name, but she still couldn't find it," Crotwell says.

Then, the schmidt really hit the fan (so to speak): Ms. S. paused, issued a couple of quiet "ohhs," and said the sentence Crotwell will never forget: "Wait a minute -- why would my printer be ... uh, you didn't mean for me to go to your computer, did you?"

That's right, gang: Ms. Schmidt misinterpreted "My Computer" to mean Crotwell's actual computer -- not the Windows icon on her own virtual desktop.

"She took it literally and just went straight down the hall to my computer," Crotwell chuckles. Once he realized what was going on, Crotwell got Ms. Schmidt back on track and wiped out her problem in no time. These days, you can bet he's a bit more careful when choosing his words.

"It really cracked me up," Crotwell says. "It's easy to take for granted how something second nature to us can sound completely different to a user."