40 IT Professionals Share Their Wildest Work Stories

Ever wondered what really goes down in the world of IT? Brace yourself for a wild ride through the tech trenches as IT workers spill the beans on their craziest work stories.

Despite technology being as essential as oxygen these days, most folks have no clue about the chaos that can unfold behind the screens. From epic user errors that defy logic to bizarre tech support calls that verge on the surreal, these tales will have you laughing, cringing, and shaking your head in disbelief.

Get ready to peek behind the curtain of IT work and discover a world where even the simplest tech hiccup can lead to a comedy of errors. And remember, always try turning it off and on before you call IT.


person using black and silver laptop computer
Photo by Kelly Sikkema on Unsplash

Back when I first started ages ago, a woman called in and said “my mouse isn’t working!” I asked her if it was wired or wireless.

“I don’t know! Why would I know that?”

“What do you mean? Is it wired or not? Is there a wire on it?”

“I said I don’t know! This isn’t my job to know it’s yours!”

So I asked her if she picked it up and walked away, how far would she get.

I was the one that got in trouble.


The unfathomable amount of CP that I have come across both professionally and independently repairing computers is breathtaking. From Mother to Grandfathers, cops to mechanics, youngsters to old folks. It’s pervasive and f*****g disturbs me. I have an in with one of the local PDs and drop a note each dime every time. No passes here. If I find it on your machine, so do the locals and the stateies.


Had a customer come in with his laptop and a bag of keyboard keys. He said he was working on his computer and received a phone call and stepped out of his home office. His cat found out how much fun it was to pop off the keys on his laptop, one by one and almost every single one.


My husband does not work in IT but he should. He worked on a facilities team at an expensive private school, and one day got a ticket to remove/trash a 75 inch TV. He approached the head of the IT department asking why he needed to trash it when he had just installed it brand new. The head of IT told him it won’t stop shutting off. My husband loaded it into the work van and dropped it at our house instead. Later he came home, plugged it in…

and turned off the 10 min automatic power off timer. We got a fancy TV for free!


the seal of the department of justice on a wall
Photo by David Trinks on Unsplash

Received a call from the FBI Cyber Crime division. Said be at a conference room at one of my healthcare clients in an hour. Got my team together and showed up.

Was informed that a large medical practice that used our software had been infiltrated by a hacker that had posted a video of himself on some kind of dark site walking around their large office (500,000 square feet) and bragging about his expertise and claiming to own our network. They played us the video. He was employed there as the night security guard. We quickly saw that he did not gain access to our net.

They informed us that he had given his notice and his last day would be Thursday. He has posted a bunch of threats to the dark site about what would happen that next holiday weekend, after he was gone.

It did turn out that he had gained access to the network of the surgery center in the same building. And he has used that access to remotely disable the HVAC system for hours at a time during surgical procedures.

On his last day, the FBI rolled up at night. Waited for the older security guard to leave the building to patrol the parking garage. Then knocked out all power and lights to the big building, lock all the doors, pulled up in about eight black vans, about 30 guys with submachine guns jump out, sweep the building, arrest him and quickly leave.

We were counseled to shut down the network for a week, in case he had planted time bombs to be triggered near the 4th of July. We did.

Turns out he had a young wife and two kids. Was offered a plea deal for three years in prison. Decided to go to trial. I was a witness.

He was sentenced to 11 years.

A twist. The pastor at his church testified as a character witness. Said he had never had an issue with him. Turns out the FBI had hacked the Church computers with a warrant and found that he had been fired as the IT guy at the church. Pastor was charged with perjury and sentenced to prison too.


An outgoing software dev put an easter egg in our ERP before he left.

Anyone who typed the word “RAPTOR” in any text field, would have a Raptor from Jurassic Park fly across their screen with a loud screech. Only 3 of us on the team knew about it.

Little over a year later during a demo of our Asset Management module a manager asked about inputting vehicles, the trainer asked what kind of vehicle he drove, “An F150 Raptor”. So the trainer, as a demo, input the vehicle description and BAM!

“RAAAAAAWWWWWWRRRRR!!!!!!!” comes screeching with this Raptor flying across the screen in a room of 50-60 people, including our CBO, and most of our upper managers. My wife is one of those upper managers so she sees me in the back of the room trying so hard not to laugh. She gave me this look like “really?”

Our boss just calmly said “Well, that’s not a bug or a feature. Looks like we’ll need to fix that.” He had no idea.

The next day he went back through the commits and saw where it originated. During an after action meeting he kept it low key and just assigned it to me and this other dev who knew about it to take it out. He finished by saying “And please don’t put easter eggs in our code.”.


On my way to a client site, the client called and asked me to pick up a pizza.

Me: “You are charged by the hour, you know that right?”

Client: “Yep”

Me: “What kind of pizza do you want?”


I did IT in the mid 90s. I had a small vacuum cleaner I used to clean out dusty cases. One day one of the people I supported came into my office and asked if he could borrow it to clean out his home PC. I said sure and gave it to him. He then continued to stand there working up the courage to ask me something else. Noticing his dilemma I asked if there was anything else I could help him with. He, with a completely serious face, asked if the vacuum cleaner was going to suck the data off his hard drive. Now I, up to that point in my career, had never laughed out loud at a user but I couldn’t contain it. The relief on his face was priceless when I reassured him his data was fine.


Not wild, but ridiculous: I drove 40 minutes away to look at a client’s computer, who said the PC was not responsive. When I arrived, he said “Look” and pressed a key on the number pad. Nothing happened. I pressed Num Lock and drove 40 minutes back.

A week later, the same customer said his computer was miscalculating formula amounts, so I drove there again. He says, “Look…I type in that I want a pint, and it prints out a formula for sixteen ounces.” After giving him an elementary math lesson, I drove 40 minutes back again and requested that he have his computer taken away.


larva, lice, insect
Photo by olivierlevoux on Pixabay

IT for medical professionals. Big institution. Doctor brings in a dead laptop, they killed it by spillin’ something on it, they were stupid and didn’t backup any data so my task was to pull the drive and recover their files.

Open up the laptop and learn it’s full of body lice. Full. So I double-bag the laptop, call Facilities to report an infestation. My shop gets tented and fumigated, their lab gets the same treatment. Meanwhile I leave work, drive to Walgreens, get a couple home de-lousing kits, drive home, strip down in the backyard and de-louse myself. May have been paranoia but I ended up tossing my clothes & the backpack I used to carry to work; I even tented my car for 3 days (that was fun) to k*ll any bugs that may have hitched a ride. De-loused myself and my dog, too, just to be safe, and cleaned my whole house like I was expectin’ the queen for dinner. I wasn’t taking any chances with bugs that a) make a livin’ by suckin’ blood, and b) were somehow survivin’ in a medical lab that had God-knows-what goin’ on in it.


I work with a lot of engineers, like literal rocket scientists. The number of really intelligent people who don’t know what simple things like “can you minimize that window” or “let me see your desktop” are is simply mind blowing. I am thankful everyday that Teams added the ability to take control of someone’s cursor.

I feel like the more advanced a person’s specialized knowledge becomes, the more rapidly their general knowledge declines. Some kind of weird inverse correlation.


Big company, couple of hundred users, each with their own network drive (hotdesking scenario, so they could get their docs, no matter where they sat in the call centre/rest of building). The server that housed the “home drives” as we called them, was running low on disk space, so we sent out emails to everyone saying the shared drives were for work docs only, and that we could see images, mp3s, mov files, etc, and that these should be deleted if not work-related.

Fast forward a few weeks and the disk usage has gone down, but still really close to full, so the lowest paid member of staff, me, was to find the worst culprits and report back on what the largest content in their drive was.

The very first person I checked had a huge drive (most under 500MB, this was 10s GBs). Sorted by size, 2GB+ .mov file, named totally randomly with numbers, like 93829084320834 – Opened it, CP. FML. The subsequent police-led s**tshow was not what I needed to be involved in at 19 years old.


Got called to investigate/unplug a laptop that had viruses detected on it. When I arrived, this laptop was in the open with the login information taped to the desk. This laptop was given local admin privileges by someone before my time for some application. This was in an office area that was always unlocked and 10 steps from the entrance of the building. No one was in the office as they went home early, including management.

On a laptop filled with everyone’s information (SSN, names, addresses, and more), Limewire, games, p**nography, and more. The two who worked on this laptop just used it like their personal laptop with occasional work being done on it.

The laptop was promptly disconnected from the network, confiscated, and returned for analysis. Yes, there was spyware and we don’t know how much personal info got out. This was reported to higher management. The two who used it disappeared quickly and quietly after that.


My colleague got a call from a customer who was a Pastor as he needed help with his computer. It was a weekend, and my colleague knew his machine name so he remotely logged onto it as he in parallel started calling him. Screen loads, and it’s playing lesbian p**n, on his work computer, in the church. Needless to say it was awkward as the pastor answered the call a few seconds later.


person holding white electric plug
Photo by Kelly Sikkema on Unsplash

Drive to an office for emergency oncall service charging the client $400+ dollars an hour to plug the power back into a switch which their cleaning staff had knocked loose.


Someone recently called my helpdesk requesting that we clear the roads so she could get to work.

“The sky is falling and waters in the way”

Meaning “It’s raining really hard and the streets are flooded”

As the IT helpdesk, of course there’s nothing we can do about that.


Got paid my on-site visit minimum of $375 to plug in a phone cord to a fax machine. The young front office person did no know what a landline was.


Lady from the office downstairs borrowed my bosses keyboard whilst waiting for a replacement.

When hers arrived she washed the borrowed one in the kitchen sink and left it on the draining board to dry out.


Other workers screen shot her windows screen, made it her background then moved her task bar off screen. She kept clicking start but nothing would happen.


Take literal magnets off of the laptop so that it would work again.


I had repaired a printer at the big insurance company. On the bill I wrote “mouse removal – NC”. The client questioned my comment – “printers don’t have mice”! I responded “they’re not supposed to. The furry little guy is in the plastic bag next to the printer.”. Eeewww.


Emergency flight from CA to GA because they were getting alarms on their new system, flew out at like 4am, got onsite at 9am, told to come back at 9pm. got a hotel, slept, came back onsite 9pm.

Customer stated that someone used a cable from the PDU to log into system but plugged it in wrong when done. But they were no longer getting alerts.

I looked at it, it was correctly cabled, apparently someone had noticed and put it back correctly. Left site and flew back home.

23 hour day just to LOOK at a cable label… they probably got charged like $10k to have me go onsite if not more…


IT problems are human errors and it’s usually because something is powered off.

200 dollars to drive 5 miles just to hit the power button is more common than you think.


I was a solo IT department for many years. Had to run manual backups on sales people laptops. I run into a huge folder, check if it needs to be backed up. Turns out it was a st ton of pics/videos of the married sales guy and the young receptionist getting it on at a company event (the company used to get us all hotel rooms). I sat the guy down and said I found some st that shouldn’t be on company property. He turned white as a ghost. I said it’s all good if he deletes it/doesn’t do that again. So I never told anyone about it. I would’ve found a way to tell the wife if I hadn’t run into screenshots of their texts—the wife had recently found out about the affair. It was really messy, kids involved.


man in brown sweater wearing black framed eyeglasses
Photo by Towfiqu barbhuiya on Unsplash

Very early in my career, back when I was still working an entry level job, I had called in sick with stomach flu. I was throwing up every hour to hour and a half, had been all day. I got called by my boss and told it was an emergency, that her computer wasn’t working, and she had something she needed done in an hour so I needed to come in and fix it, sick or not.

So, in between bouts of puking, I drove across town and plugged the power cord for her monitor back in. Not even the end in the monitor itself, the end in the wall. She hadn’t even taken 2 seconds to make sure it was plugged in before she dragged me in with stomach flu to fix it for her.


Working with the Judicial system, it wasn’t uncommon to see photo / video evidence of child abuse or neglect. People do some really f****d up things to kids.


I had to remotely install a spyware program on a VP/CFO’s laptop because loss prevention was trying to gather information on him. The software recorded keystrokes, program usage, web history AND videos of what he was doing on the laptop.

He resigned the next day after they found that he had a girlfriend in one of the company’s manufacturing plants in China. The guy lost a million dollar job for that. Probably lost his wife and home too.


This wasnt at work but at a lan party. Had a guy in a CS 1.6 tourney had a system was constantly overheating and locking up. Opened it up to find it caked with dust. A few people split the job of cleaning it and I was given the cpu heatsink. I didnt have my tools and all I had was some plastic untinsels and with what was in the bathroom. The sink was too small to get the heatsink under it and the knife was not getting it off. So I just stuck the heatsink in the (relativly clean) toilet. All of the caked dust and gunk came off. I was able to shake it off, put it under the air dryer, apply some thermal compound on it and put it back in the machine. The other guys got the rest of the system cleaned up.

I didnt tell him I flushed his heatsink in the toilet.


Got paged one night because of a data outage. Turns out one of our on-call response folks went into the server room, locked themselves in, and unplugged several machines. This caused several data outages, which caused a page and thus someone driving in to resolve it. This was a major military mission critical system and this guy thought the best way to get someone’s attention was to break a bunch of stuff.


white projector
Photo by Chirayu Trivedi on Unsplash

Walked all the way across campus in the Florida heat just to tell a PhD professor that the reason their monitor kept turning off every few seconds was because the computer was in fact turned off. Then got yelled at for her classroom not being ready for her when she came in.

Also was told to “make sure these projectors aren’t in the building by the end of day. Don’t care where they go, just that they aren’t here tomorrow” by my boss. It was more expensive to buy new bulbs for them than to just buy new ones so that’s how I ended up with 5 projectors that lasted years.


I just flicked a defective screen back to life not 2 minutes ago. Like a small laptop screen that just would’nt turn on even after taking it out and putting it back in. Then I get uppity and flick it and boom…

Actual craziest was a fired employee who was wildly underperforming coming to give back her laptop. I booted it up and she had a contract and payslips from the other company she was working for with our stuff. She was dumb as a rock and HR tore through her case…


I walked into the office one morning to my CEO asking me to follow him to his office. He pulled out a stack of paper, almost a full ream, of printed p**n from our network printer and asked me to find out who sent it.

Back then, most of our office staff had their own desk printers. I assumed that this person had worked late and meant to print out these pics on his local printer. Our CEO only used the network printer near his office and gets to work well before everyone else. Obviously, dude was fired.


As a consultant software dev, I got called into a client office on a Saturday to help fix a hardware issue because the regular IT staff was non-responsive (they sucked).

We were changing a bad memory card on a server, and my boss asks me to unplug the top box. I was averaging about 90hrs a week so I was f*****g cooked, and I unplugged the wrong machine.

This was a travel agency call center doing $1M/day and this machine was in the call center server stack. We freaked out of course, and my boss walked out onto the call center floor, quietly asking if everything was running ok LOL.

Luckily it was a benign marketing server and everything was ok. Lesson learned, don’t let the software dev in the server room.


Had to spec out a state of the art, no limit small computer for the CEO. I give two options, one best in market skull logo on the front. The other not as good and no skull logo. I submit to my boss and he says CEO will probably never go for the skull one as it’s unprofessional. I look up a plate to cover and add that in.

Like a $10k computer alone, 5k monitor.

CEO went for skull icon one without plate cause it was best in market and skull looked cool.

My boss wasn’t happy to be wrong.


Back when I worked as a help desk tech at a government facility- I was sent on a call to put in new desktop for the office manager as she hated laptops.

I set an appt time up in outlook for her, block out an hour off her schedule and swing up there.

There she is, a very large elderly office manager sitting in her desk. There under her desk is the tower I was to replace.

I introduce myself. She backs her chair up about a foot and says “OK, have at it.” and powers off her system.

I stand there looking at the one foot of space between her lap and the spot under her desk. “I am going to have to ask you to slide your chair back as I need to remove and replace the tower.” I state.

She skootches maybe another foot back and blankly stairs at me.

So, I hold my breath and go down under her desk. Thats when I notice the 10-12 filled pee bottles under her desk. Yes. Pee in old Gatorade bottles just tucked away under her desk.

I ripped the tower out and said “I will be back ASAP I need to clone your hard drive.” and GTFO.

I sent my intern to go install the new one.


Hiding a “k*ll switch” in the code of a web application we had because my boss thought the customer would try to steal our code. Just to add, my boss never used the switch, but they did stole our code, I already left the company, but as far as I know there’s a lawsuit going on, I remember having to help my boss gather proof of it to share with the lawyers.


We had an after-hours call to the hospital we work at because our new unit secretary in the ER couldn’t find the remote to the TV they have that show where patients are located.

It’s also an application that’s loaded onto every computer in the nurse station. She was fired a few days ago after trying to throw us under the bus for her f**k up.


Not me but a colleague had to sing a lullaby to a user because she said she needed to be calmed down. (had to might be the wrong word, but he did do it).

She was insanely unstable when it came to service workers. She was the head economist at the specific company handling a lot of money. So she was basically babied no matter how many times we complained to her boss.

She would call in screaming refusing to let us do anything while expecting us to fix her problems telepathically. She had non issues every day, so we basically existed so she could torture us.


Explain to the Chief Technology Officer that having the prod server and its backup server sat next to each other, may well save cost on not having two data centers, but when that data center (also known as the stationary cupboard…) goes, it’s not such a money saving idea….


a sign that reads sex shop on the side of a building
Photo by Pat Moin on Unsplash

I used to work for a “non-profit” case management organization. Most of my end-users were case managers trying to take kids away from their s****y parents. All of them were issued laptops and cellphones. We tracked these devices closely. I picked up a ticket from this one girl who lost her phone. When she opened the ticket she CC’d her manager so i thought it was only appropriate to reply all, with the last known location.

After sending them the address i got curious and plugged it into google. It was a well known adult toy store. The girl eventually replied, “I DID NOT GO TO A SEX SHOP!”

Read More: 40 Funny Work Memes To Keep You Laughing Through The Week (June 24, 2024)

Alex Buscemi

Alex Buscemi

Writer. Billionaire. Astronaut. Compulsive liar.

@whatsupboosh on socials.