Your Horror Stories About Nightmare IT Workers

Illustration for article titled Your Horror Stories About Nightmare IT Workers

We asked for your worst encounters with difficult IT workers. From actual spying to crumbling infrastructure to people who had HR on speed-dial, you’ve endured a lot. These are your stories.



ArchitectQueenBitch wrote:

I had an office IT guy aid and assist a jerk in our civil department who was really creepily stalking me and when I took it to HR found out 3 other women in our firm had the same issue with the civil jerk, but none of them had been smart enough to know the IT guy did it. He was letting civil jerk look through my office emails, not that I’m stupid enough to ever send anything inappropriate through office email.

I figured it out because creepy guy referenced something I said in an email to my boss about taking the day off to look at new apartments, and I wasn’t sharing it because coworkers knew my then boyfriend and I didn’t want him to know I was moving out. When the civil guy emailed me and was like “I heard you were looking for a new apartment, maybe I can help” I got super creeped out and went to HR. We both knew the IT guy was the only one with the power to let people in to others emails. Unfortunately the IT dude was the brother of the firm founder... needless to say I found a new job asap.

Calling Comcast Support

theburners wrote:

“Hey, we had internet access, your guy showed up to install cable for the house next door, and now we have neither internet access or cable TV (hey, its my parents, they’re not ready to cut the cord). Pretty obviously you. I already factory reset the modem and the router just to be sure, but the cable modem/router isn’t pulling anything from DHCP. Pretty sure your guy nicked a cable or something”

“Please unplug the power from your cable modem and wait for 5 minutes and plug it back in”

“Like, literally the moment he got up on the ladder we lost access”

“I am sending an activation signal to your cable modem”


We got internet access back... a week and a half later when they sent the guy back to fix whatever he unplugged.

When The Nightmare IT Is You

Caleb drives his Malibu, silently sobbing for want of an Avant wrote:

I just might be one of those “nightmare IT workers.” I work for the IT department at my high school, and as part of our tech program every student gets a MacBook air which they buy over their four years. So anyway I am one of the most trusted tech mentors as it they are called, and I have been tasked with finding ways around our filters, both on campus and off. And our filters are good, damn good. None of this pansy shit, they use CIPA, iBoss, and a proxy developed on site, with quite a bit of help from yours truly. While attempting to find a way to bypass the filter I stumbled across a discovery: if you used three specific chrome extensions you could bypass the filters, and your history would be unaccessible (That’s another gem of the system, all of the student’s internet history is stored on campus, down the road at our sister grade school, and an offsite server center in Chicago).

So being the money crazed 16 year old I am, I turned around and would perform an “operation” on people’s laptops for fifteen dollars a pop. A few days later, I would report to my supervisors that I witnessed a few students bypassing the filter, we watched their screens without their knowledge, hauled them in, and undid what I did for them, remotely, of course. A day later or so, they would come back to me saying that something had gone wrong, but I was happy to fix it, for $10.

By my count I’ve made over $150 to date.

Rampage_Rick wrote:

Most of us take a turn towards the dark side at one point. The memorable one for me was when our hospitality manager (2 scoops of looks, 1/2 scoop of brains) really pissed me off one time. As I recall the original issue was her A/C not working properly (insufficient cooling, clogged filter?) which is not really an IT issue. She didn’t like that answer and became quite belligerent; I left.

She phones across property to our VP of Operations as I’m nearby his desk and she starts spewing heaps of make-believe “wrongs” that I’ve bestowed upon her. I don’t think the VP really cared either way but I just threw up my hands and left... Went back to the IT dungeon, pulled up the CCTV camera near her desk, and began dicking with her workstation. I wouldn’t do anything while she had a customer, but the second they’d leave I’d pipe an MP3 file to the IP of her receipt printer. A 3-meg MP3 equals about 6 feet of gibberish. Ten minutes later I’d remotely reboot her PC. Then another MP3 to her LaserJet. After an hour she sheepishly called me back to troubleshoot. The diagnosis: The faulty A/C must be interfering. I walked over to the breaker box and *click*. Went from shitty A/C to no A/C and the computer problems vanished. It was only about 32°C/90°F outside.

She later got canned for submitting a timesheet that included her week on vacation in Costa Rica... (we get 4% additional pay in lieu of paid time off) I dutifully provided printouts of the photos she posted on FB as well as access logs that proved she didn’t remote in once.


Kysimir wrote:

We had a female NCO (think frontline manager) who was - shall we say - difficult and had a tendency to break things without taking any sort of responsibility for her actions. Well, one day she accidentally unplugged the UPS under her desk from its power source and it started beeping.

A frantic phone call later, my coworker and I were on the watch floor getting berated for a beeping computer, and emphatic instructions to “fix it now!” Unfortunately, the desk was about 24” long and 600lbs, and ontop of the power and network drop in the raised floor.

“Ma’am, we’re going to have to shift the desk and unplug a bunch of stuff to get to the power conduit.”

I can’t recall what her next tirade consisted of, but it ended with “I DON’T CARE. NO MORE EXCUSES. MAKE IT STOP BEEPING, RIGHT NOW.”

At this point, we had been working the issue for about five minutes, most of it being yelled at, and my coworker had enough when he asked slyly, “Make it stop beeping?”


He reaches down and you hear a long BEEEEEEEEEEEEEEP.

Her entire desk, consisting of about six workstations cuts off.

Dead silence. After a moment, another customer, a favorite of ours for his sarcastic quips, looks at the NCO and says, “Well, you said you wanted it to stop beeping.”


Horror Bosses

JasonGW wrote:

I could go on for days. So, I was the Sr. Engineer for a law firm, and the IT director had recently been hired by the CEO. He was a friend’s son (yet still in his early 50’s) who’d never worked in IT, and he decided on day one to fire the 20+ year administrator. I found out when I walked in the door that he’d been fired about half an hour before my arrival. When I walked in, the first question was, “Why did the email system go down this morning?” Mind you, I’d never so much as logged into their network, and had no way to know, but I figured it was probably a dick IT guy who tied important services to his user account.

I was right, and had things back up in short order, and by the end of the day had untangled the twit’s idiotic attempt to keep himself relevant (pro tip to young people starting in IT: no, using your own account as a booby trap for services will not save your job).

Anyway, I learned in short order that the new IT Director was, in a word, stupid. I mean PAINFULLY stupid. Their 9 year old Exchange server was almost out of space, and was already maxed out on capacity. I informed him of this, and found a suitable new server for about $4,000. He said “we’ll see”. The next morning, I came to work and found a box COVERED in dust on my desk. The IT director walked over, grinning. “Solved our mail storage problem!” he said. I opened the box, and it was filled with old 18.2GB SCSI hard drives. Several of them had post it notes reading “bad” on them. But on top of that, the server was old enough that the max capacity its SCSI controller would support was 9.1GB per channel, and was already maxed out anyway. I informed him this was useless and explained why. He walked away angry.

The next day, an old server, identical to the one we already had, sat on my desk. “Found it in storage where the old drives were”, he said, and handed me a server cloning software CD (I forget what brand, but it basically did byte for byte mirroring and was designed for failover scenarios). “Use this to make a duplicate of our server, then our problems are solved!” Again, I explained why that wouldn’t work. Again, he walked away angry. I went to his office and explained to him that the $4,000 server I’d spec’d out would solve the issue. He said “We’ll see”.

A week goes by. He calls me to his office and says “I have good news. I got them to approve $5,000 to bring in a consultant to look at the mail server.” I couldn’t help myself. “Did you fail basic math?” I asked. “For $4,000 we can solve the problem. We don’t need a $5,000 second opinion.” He refused to listen, and the following Monday the consultant showed up. By this point, I’d tracked the average incoming mail flow per day and estimated we had about a month before the drives filled up and the server stopped. The consultant, I later found out, was a friend of the IT director’s. He asked about all the same “solutions” as the IT director suggested, and in the end wrote up a recommendation that mirrored mine: replace the server with a brand new one.

A week before we were ready to run out of space, I tried again, but he refused, and said “somehow we’ll figure it out”. So I quit and walked out, because I know how this works: if you’re the Sr. engineer in charge of something, and that something goes tits up, you get the blame, even if you did everything possible to solve the problem but got stymied by management.


JohnHinesJr wrote:

I was the DBA for a medium-sized software company. About half the employees were devs or other technical positions. The IT department was headed by a guy who was really into martial arts, and not into doing his job. Instead of configuring an internet filter, he had his guys create a white-list of acceptable websites. The list contained 10 entries. Fortunately, Google was one of them. Unfortunately, unless the result you found was on Amazon or The New York Times, there was very little chance you could actually see the information you needed.

His office was configured so that his back was to his window. When standing in front of his desk, his computer screen was reflected quite clearly in the window. So, whatever martial arts blog or porn site he was currently surfing was on display.

The saddest part was, he seemed to be immune to being fired. No mistake was ever his fault. I shudder to think what leverage he must have had over the company’s leadership.

The same guy was struggling with an overheating problem in the server room. His solution was to bring in portable A/C units and turn them on in the room. They were vented into the same room. He couldn’t wrap his head around why the temperature kept climbing, no matter how many units he rented.

When I gave up and left the company, he was still there. I kinda hope he still is.


LarsVargas needs more powah wrote:

We had an interim CTO at an Internet company I worked at as a developer in 2009 who was just weird and creepy. But he generally kept it to himself. One day I was walking by his desk and my eye was drawn to movement on one of his machines, a netbook. I then noticed that the movement was video of me walking by his desk.

He had a live web stream going to a public server on some “hacking” web site along with audio. I asked him to stop it immediately, and he denied it was even there. I didn’t want to get into ab argument about reality, lies, and creepy behavior with a guy who had access to all sorts of personal data on me and knew where I lived. So I requested loudly — so everyone in the department and nearby could hear — that he no longer broadcast what we’re doing as it exposed trade secrets.

It wasn’t a problem that re-occurred as he was escorted out a couple of days later by armed security the company had hastily hired. Seems this guy also had a gun fetish and wasn’t shy about sharing info about “his guns” with the ladies of the office in a not-slightly-menacing way. On his way out, he shouted, “You will all regret this!”

So armed security stayed at the office for at least a few weeks after that. Fortunately, nothing ever happened beyond a threat.

At the same job we had another developer who would surf porn at his very visible desk and leave it on-screen. He was told repeatedly by various people of various management levels to cut it out, but was not deterred. Oddly enough, he wasn’t creepy. Just a jerk who apparently couldn’t go more than an hour without looking at exposed human female breasts. He also frequently took naps under his desk, nude images still on his monitor.


sneezeaaah wrote:

We put in a database system that cost $3 million and 18 months to implement. The IT guy in charge refused to allow any one to access the database to mine it, in his words “because I am the one who is in charge of this and I will be the one one held responsible for its security”.

He created a huge “justification form” wherein each one time request for data had to be justified in writing and approved through several levels and took weeks to fulfil. Any requests to speed this up met with “That is not my only job and you are not my only priority” as a response.


Amaries wrote:

Our infrastructure manager once took over my work station and IM’d my resignation to my manager. :(


Have You Tried Turning It Off And On Again

bigPixel wrote:

Our IT department recently “upgraded” our corporate antivirus. On tuesday it decided my wireless keyboard was a malicious USB device and disabled it. On wednesday it decided my boot drive (the internal hard drive) was an externally-connected malicious USB drive, and disabled it. Today, it decided my monitor was a malicious device, and disabled it.

So yeah, in my recent experience, corporate IT are all about making sure we can’t use our machines.


JasonGW wrote:

Here was a fun one: A new employee, Sally, came to my office complaining that in the three days she’d been there, no one outside the company had received any email she sent. Internal email was flowing fine, however. Our email address policy was first initial, last name, so for example Joe McDonald would be I opened up a management console to hunt down her account, and realized we had a surprising number of Sallys in the company, so I asked her last name. “Lut”, she said.

*Facepalm*. No wonder nobody got her emails.

You Might Need An Update

echo wrote:

Not exactly a “fellow-worker”, but a guy I came in after: I took over a 1-tech shop for this retail company and the Dude Who Came Before left the place in an absolute wreck. Hard drives, both bad and good, all mixed together and just thrown everywhere; ram sitting out all over the desk, a 3-ft diameter ball of AC adapters that were hopelessly knotted together; absolutely zero AD Group Policies defined; everyone had local admin rights to their machine, even sales/accounting/warehouse/etc.

I would randomly find things like 56k modems (this was 2013!) in our stores, or 5 port switches daisy chained together for no reason, and everything was always zip-tied together under people’s desks, which made changing monitor cables (seemed like it was at least a weekly thing) a pain the arse. His idea of fixing broken motherboards was to try and replace capacitors by himself instead of either a) getting an RMA, or b) just buying a new effing mobo. My ‘training’ consisted of about 3 hours of “this is how our network is set up” and he was out of the office the entire rest of the 1-week overlap. His idea of monitoring was “here’s a text file of an nmap I did 3 months ago”. I spent the first 2 weeks just cleaning up the office, and the rest of my time there cleaning up his other messes. Absolute tosser of a tech, and somehow he got a job somewhere else. OH and the best part: he got paid more than I did with access to a company car, except we were doing the exact same job. Damn you, Rob!


Thunder wrote:

When I started working at my current job as a network admin, the “data processing” manager (seriously, he insisted on calling himself that) had already completely checked out. He was of the opinion that less is more so I discovered an aging and severely dilapidated infrastructure on the verge of collapse. Apparently his superiour thought that if his IT budget was small, it meant he was doing a great job. This meant all computers were at least 8 years old (celeron based gx60s), some mac servers upwards of 12.. in a production environment. in 2011 there were still blue and green bubble mac machines being used to generate content, and those offices using them would have a communal workstation that was just modern enough to allow them to access the internet.

This guy wouldn’t let any of us who were more qualified answer any questions sr management asked, we had to filter through him which was about as effective as attempting to explain quantum physics to a tree stump. Two years we fought through this dude’s fog until thankfully he was retired so a real manager could take the helm. In all seriousness, we have NO idea what he actually did during the day when he was “working”.. he didn’t complete any projects, he didn’t assist on any plans (or even understand what we were saying) and single handedly drive the company into an IT pit of doom that we are STILL digging out of.


Barely Legal

onesadpanda wrote:

Worked for a small IT consulting firm in an East European country. It was ok for a while and, even though I didn’t get compensated for overtime, I was happy with the job. One day, the manager came to me to ask why I only had clocked in about half the time on the previous month. It didn’t mattered to him that I took paid vacation for two weeks. About three months later, the state anti-corruption agency stormed into our firm. I kid you not when I’m saying that I’ve seen computers thrown in the trash and HDDs flying to a neighbour’s back yard. We all got to go home early that day. No arrests were made, but the big boss is now facing deep corruption charges. I got out of there ASAP.


TheBlightofGrey wrote:

In the early 90s when web-based porn primarily consisted of photos on listservs I worked for a state agency in a western state. The network was run by one guy and two assistants. The assistants were complete idiots. They would come around and try to fix things and usually the head guy would have to intervene. The network was unbelievably good though for those days. Later I found out the head guy ran a bunch of porn sites on the side and intentionally hired the idiots so they wouldn’t know what he was up to with his side business. That guy knew the value of having a system that didn’t go down. Best IT guy ever. And from the government’s perspective- worst IT guy ever.


codeonthis wrote:

Jezebel was marked by the Admin as pornographic. I got flagged and got called in to talk about it. This is the same company that would global flag the word “Twilight.” Google Twilight, you were flagged. Go to the wikipedia page for Civil Twilight, you were flagged.


Makes You Think

HolmerS wrote:

I’m sure I’ve ticked a few off over the years though. IT can be pretty soul-less. Most of the jobs I’ve had over the years involved automating office processes at some point and that meant people losing their jobs because I did mine well. It’s bad enough when you have to disable accounts on users who lost their jobs for other reasons. When you know you caused it (however indirectly) it can get to you.


The One With Gary

AtomicSnowman wrote:

Okay, so without the entire backlog... We’ll call this guy “Gary” (his real name is really weird). Gary had a 2 year degree in MS administration and 3 years of experience in the field. Had his Network+ and A+ and a few other reasons to think he could handle the job. The interview is designed to vet pretty hardcore so the guy should have known his shit. Well, that wasn’t true in the least. Gary spent a few weeks working at a customer site doing cutover stuff for our MSP so nobody really knew what he was up to for almost a month. Finally he arrives in the main office. Gary looked to weigh about 85 pounds, was very soft spoken, and EXTREMELY passive aggressive. He constantly deliver backhanded compliments, had to have the last word, and would whine his ASS off if you asked him to do anything.

I spent a couple hours on his second day in the office explaining to him the basics of file permissions. After that he complained that I was being condescending and mean. Well it was a small office so our HR guy just sorta jotted it down but he could hear the interaction and knew it was nothing of the sort. This sort of thing happened constantly. We’d ask him to do something he claimed to know how to do and he’d be incapable of doing it without someone holding his hand. Finally he told HR that we were discriminating against him because he was gay (we kinda figured, but he didn’t talk about it so neither did we).

Ironically the HR guy, who we loved hanging out with, happened to be gay as well, and knew there was no way we were doing anything of the sort. We just got frustrated with a guy who was completely incompetent. After about six months this stick man started complaining about pain in his wrists and got himself put on the disabled list. Got himself a fancy doctor’s note saying he should only be working at his desk 4 hours a day. Well, he’d only been doing about 1 hours worth of work a day already, so we figured the net change would be negligible. They put him on field service duty so he could actually get stuff done and he’d start fights with customers about how he was going to do things his way or the highway, never followed their direction, etc.

Eventually I get promoted and maybe two weeks after that Gary emails me to tell me I’ve been being mean to him since my promotion and if I didn’t stop he’d make a case with HR. I just forwarded it to my boss and HR and didn’t talk to him about anything that wasn’t very specific instructions about my job. Business as usual, really.

FINALLY the sun peaks through the clouds. We’re going to fire the waste of space! I get pulled out of a meeting to shut down all his shit, and wipe his phone (yay!). Not long after I’m instructed to go through email archives to check communications with certain recipients, including HR, and forward the archives to the owner and internal HR person. Gary was spending 2-4 hours of each day transcribing everyone else’s conversations and forwarding them to HR. Using terms like “with a snippy tone” and “disrespectfully told me to do my job”. I will give you that me and another guy (we’ll call him Frank), there would talk shit to each other all day long. Well, these conversations would make it into these emails to HR. If implied that Frank was a man whore, Gary sent it to HR. If Frank implied that he like women with huge... tracts of land (and this actually happened and was in an email) Gary informed HR.

Gary was offered 6 weeks of severance. Gary turned it down and said he would sue for wrongful termination. Gary spent probably spent $30k trying to win that case. Gary deserved to lose. Gary lost.


Did we miss your nightmare? Are you currently sitting next to a coworker who’s about to erroneously report you to HR? Tell us in the comments—but be careful. IT is always watching.

Top image: SNL: Nick Burns, Your Company’s Computer Guy




Every IT person working telecom support’s nightmare:

*ring ring*

Okay, can you, more specific? What does it look like on your device when the “internet doesn’t work?”
I literally don’t know what the problem is because you’re not giving me more specific information.