Tales From IT Helpdesk Hell (Vol II)

IT Helpdesk techs are a special breed of superhero. Instead of capes, they don glasses and a headset. Instead of a radioactive spider bite or science experiment gone wrong, their superpowers are forged through training and experience. They don’t have telekinesis, pyrokinesis, chronokinesis, or any other type of “kinesis”. But they do have an extraordinary ability to solve complex technology issues while — perhaps most impressively — politely handling the tech-illiterate public without mutating into the Hulk like Robert Bruce Banner.


These modern-day IT superheroes devote their lives to helping others navigate the complexities of technology, and that’s no small feat! But, even the most pious tech pros can have bad days on the job.

Sometimes, the best medicine for a bad day is a good laugh. Welcome to Tales From IT Helpdesk Hell, Vol II.

PS: If you missed our first installment of Tales From IT Helpdesk Hell, check it out here

Without further ado, here's Volume II of Tales From IT Helpdesk Hell as told by the people who survived them (the IT Helpdesk techs themselves).



Help for even the most versatile technologies…

This story is sure to give you a good laugh; submitted to our good friends at Spiceworks.


One morning a lady calls in for Tech Support...because her coffee cup holder is broken...After confirming the details, my buddy tries to explain to the lady that there are no "coffee cup holders" on any of the company's computers — to which the lady insisted that hers has a coffee cup holder and it's broken...

Finally (after more frustrating exchanges), my buddy asks, "OK, Ma'am...please tell me, what do you do when you sit down at your computer in the morning?” Her reply:

"Well, when I get to my office...I put my stuff away and push the power button on my computer. Then, I go get my morning coffee. When I return to my desk, I push the button on my computer that makes the coffee cup holder come out — but when I push it now, nothing comes out."

My buddy (shaking his head) says, "No problem, Ma'am...we can fix that right away..."



Tech on the fritz with a bizarre twist…

This story come to us from the brave technicians at SysAid


I had several service calls to a lady who’s system kept locking up. Over several months she had several other problems (keyboard quit working, bad system board, etc). When we talked to her and several other office workers, we found out that several other pieces of equipment in the office were giving them problems — things like the copier, phones and fax machine. We talked to her further and found out she had a pace maker. We put a ground strap on her for a day, and she did not have any problems with the computer. The only problem with that was it interfered with her pacemaker and did not let it function as well as it should. I guess she just had to use pen and paper after that.


When the solution is black and white…

This story was shared at Windowusers.org


Received a call from a new user wanting to know why her documents were not printing in color. I told her that the printer is a black and white laser printer She said well the program said what you see is what you get. I told her again that the printer only prints in black and white. She continued to blame the software and her computer and wanted someone to come take a look at it.



My favorite Helpdesk hell story:

This story was submitted by SherpaDesk user Josh Rice (we've sent him his Yeti hat!)


When I started my IT career, I worked the help desk like most IT professionals. One day I got a call that left me dumbfounded.

Caller: Hi, my keys keep getting stuck on my keyboard..

Me: I’m sorry to hear that, did something happen to get spilled on it?

Caller: I may have spilled coffee on it.

Me: That’s alright, accidents happen. I would recommend trying to clean in between the keys, and if that doesn’t work, we’ll get you a replacement.

Caller: Okay I’ll give that a shot.

PC from hell

The next day:

Caller: Hi, I called yesterday about my keys on my keyboard getting stuck.

Me: Ah, yes you talked to me, how did the cleaning go?

Caller: Well, the keys aren’t getting stuck anymore, but the keyboard isn’t working either.

Me: Oh my, what did you try to clean it with?

Caller: I just threw it in the dishwasher.

(Had to mute the phone so they didn’t hear me laugh at them!)

Me: Well that was a creative way to try and clean the keyboard. I will have a replacement keyboard over to you soon!



Have You Gone Through IT Helpdesk Hell?


We would love to hear your best stories to publish them in our next newsletter. Submit your best IT Helpdesk Hell Tales anonymously to Yeti@SherpaDesk.com. If your story gets selected, we’ll send you a nifty Sherpa hat, said to provide the user with Zen and understanding during the most challenging IT Helpdesk Hell calls!


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Jessy Smulski
By Jessy Smulski

Jessy turns tech talk into thought-provoking stories for readers and leaders across the country.