I almost created my own brain hurty moment just now but luckily, I was able to stop the train from going off the tracks.
One of my coworkers is out sick but has some documents she needs to finish and send to the client. She called and asked me to send her laptop via messenger service. No sweat. Only I got back to my desk and started composing an email to her, letting her know her laptop was on its way and she could expect it within the hour.
She would have received said email upon opening her package from the messenger and logging on. Duh.
This reminds me of our IT department, which sent out an e-mail to tell us the e-mail server was down.
I worked at a place that had a very temperamental server connection. This was because they had this clunky security software that talked to the server in an awkward way. (Won't be more specific than that because it will take too long to explain.) This was in reaction to two hacking incidents over five years. The best solution would have been for us to use some mainstream, well-supported software but they opted for some bargain-basement deal instead.
Sometimes this software would get caught in a feedback loop and they would have to get a hold of the company to fix it. Said software was set up so only techs from the company could fix it because the company was again too cheap to pay for our network admin to get trained.
The network admin would always send out emails saying, "We have a feedback loop, but you can bypass it by following steps X, Y and Z..." And of course we couldn't get the email! The network admin would barricade himself in the office to hide from the hordes bothering him for a print out of the work-around.
Our director kept saying, "Well you shouldn't have to have dead time because Bob always has a work-around!"
*headslap*