We're All Administrators (from Tzveta)
My day job is in the IT group at a particularly large educational institution in the southern United States. We recently acquired a new high-end document/imaging system and were running into some problems getting it configured and running; the Associate Dean was not happy about this.

"Help me understand why we can't get the new printer/scanner to work?" he asked frustratingly, "it's been two days since it's come in, and every day it's not up, we're burning through money doing all this stuff manually!"

"We are trying to figure out what's causing the problem," I responded, "it seems that the printer software only likes being run by users with administrator rights."

"What!?" the Associate Dean barked, "who do you think works for the university!? Everyone who works here is an administrator and should have administrator rights!"

"Err, no," I said, "it's a security privilege, it's more about administering the computer than—"

"That's what we do!" he interuppted, "I am an administrator for the University, what kind of ridiculous set-up do you have here that I'm an administrator but not an administrator?"

The conversation didn't get much more productive than that, but fortunately the vendor had a workaround, and we were able to convince the Associate Dean that he was administrator.

 

Zoologically Educational (from Troy)
I was called by operations to research an issue with the email archiver process. Basically, our archiver looks into everyone's mailbox, takes any emails flagged "archive", converts them to PDF, and then ships them off to some long-term storage system.

For some reason, the spooling service kept stopping, which caused a whole cascade of other problems. After spending the better part of a day tracking things down, I discovered that a single to-be-archived message was causing the whole thing to grind to a halt.

I needed to figure out what this rogue email looked like, so I opened up the file. It was an email sent from jane_bivins to jane_bivins with a subject line of AAA and a blank body. There was a JPEG file attached, so I double-clicked on that, too.

What I saw was... surprising... and, erm, zoologically educational? The image showed two goats that were very tightly coupled, and the picture was shot in an angle that provided more detail than I would have thought possible. And for whatever reason, Jane Bivins decided that this picture of two goats was so important that it must be saved in the company email archive.

Deleting the email seemed to fix the service, and I never could quite figure out why. My only guess is that the PDF archiver had somehow become self-aware, and was protecting the archive out of good taste.

 

White Space (from Caitlin)
I'm not quite a follower of the Nick Burns school of tech support, which means I try hard to not make my users feel stupid. Even if the problem very clearly exists between the chair and the keyboard.

One of the folks in marketing called the helpdesk to report that her keyboard wasn't working. A phone diagnostic was basically impossible, so I visited her at her desk to see the problem in person. It was immediately apparent that the keyboard was working just fine, but that characters typed in Word were not visible. The cursor would move forward, but nothing appeared on the screen.

After staring for several beats to make sure I wasn't wrong, I pointed out as gently as I could, that her font color was set to white. "But that doesn't really explain the problem," I added, "and I'm a bit worried because I don't know how font color would have changed all by itself, or even with a keystroke that would have hit by accident."

"Oh wait," she said, "actually, I was using white on the previous page!"

I wasn't quite sure what to say after that.