5 + 1 true hair-raising IT admin horror stories

When we were kids, we used to make up scary stories and scare our friends. The one with the most horrifying story would be the coolest. To (re)claim the coolest status, we would exaggerate. A lot.

But, now as grownups, we still have some scary stories to tell. Only now they come from the place of working as an IT Admin. And they are 100% real.

We asked our team of IT admins to share their most terrifying work situations. Their answers gave us giggles, wide-eyed disbelief, and snorts of amusement.

So, without further ado, here are the scariest stories we’ve heard.

1. When your workplace becomes the Survivor

It’s midnight. I worked for a giant gas station chain with stations across the state. We did our regular server updates after the cash register reconciliation, after midnight, when there were generally no customers. I made a cup of tea and clicked the “update” button.

Suddenly, my phone explodes… with text after text after text.

The update process lasted longer than usual. And there were customers in front of the gas station this time. Did I mention it was Christmas Eve?

Yes, it was Christmas Eve. Suddenly, the crowd lost its patience, threw the plastic barricades aside, and banged on the gas station window. Gas station sellers started texting me, asking me to end the server update.

Just as I was beginning to think I was going to become a victim of a siege, the server worked, and no one was hurt. I guess in the end everyone made it to their Christmas turkey on time.

Takeaway

Well, I guess the moral of the story would be: “No customers” can turn into a Christmas crowd riot in the blink of an eye. Or in server update time.

Borna Kušić

2. When you just want to work…legally

Years ago, I worked for a tech company known for its relaxed, laid-back culture.

Silly me. I thought it was related to standard industry perks, you know, like a ping-pong table in the conference room and a kitchen filled with snacks and drinks.

As it turned out, it wasn’t the case. It was about their approach to work.

During an external ISO 27001 audit, the auditor asked me to clarify the process of access reviews for confidential SharePoint sites.

I couldn’t have told him the truth: we review it only occasionally through PowerShell scripts without evidence of historical views.

And the funniest thing is that their company culture wasn’t laid-back at all. People were stressed out, and that ping-pong table in the conference room was the best dust collector ever.

Takeaway

Maybe if their ISO compliance routines were tighter, they could perhaps afford to be a bit looser. 

Dejan Štefulj

3. When you have the best intentions

I was a student, and my biggest career wish at the time was working for this particular company. It was a significant company in the town where I grew up, and only the best of the best were working there. I did get the opportunity to work there as a student. And I wanted to make an impact.

So, I’ve decided to upgrade the RAID controller firmware.

By myself, at the age of 20, on a Friday evening.

Let’s just put it this way: The firmware upgrade was unsuccessful, and the entire RAID field, along with all its data on the only company server, was unavailable. Needless to say, there was no backlog existing.

I spent the whole weekend trying to restore the lost data. I succeeded, but boy, oh boy, was I close to moving to Antarctica.

Takeaway

Don’t leave your students unsupervised. They could get some crazy ideas

the author mustn't be named publically😊

4. When your boss buys a new laptop

I worked for a law office, and one of the partners bought a new laptop. He wanted to transfer the data to the new device manually. Long story short: his OneDrive sync was on. All his files were copied, all 4,000 of them.

Our work hours were until 5 p.m. He called me at 5:15 to help him clean 4,000 duplicated files because he had an important case in the morning and needed to have documents sorted.

I’ve spent the whole evening manually writing a PowerShell script to delete the duplicates.

Takeaway

Always double-check your sync settings. Or you might end up with 4,000 reasons to cancel your evening plans. Or your IT admin’s plans.

Borna Kušić

5. When you’re just an overwhelmed newbie

Right after the above-mentioned law office, I started working here at Syskit.

The first day I was so overwhelmed with everything that I accidentally turned off the main Domain Controller.

We turned it on right away, nothing happened, everybody was cool about it. But, to this day they call me Borna, the DC Slayer.

Takeaway

Sometimes there are buttons that must not be pushed. Resist the urge.

Borna Kušić

6. When Marketing keeps asking you to participate

The scariest scenario of my life was when I received an email from you asking me to write down my scary stories.

I don’t have any scary stories to tell.

Sorry, hope this helps anyways.

Takeaway

Hm, what would be the moral of this story? Maybe not all IT admins have scary stories. Some of them just have smooth sailing thanks to great tools. But toss a bone to your Marketing department when they ask for help.

Zvonimir Pavić

Don’t be on the IT admin horror list

Sure, we can all laugh at these stories now, but in the moment – they were anything but fun. They’re the stuff of IT admin legend for all the wrong reasons.

The good news? You don’t have to go through the same stress.

A little planning, a bit of caution, and you can save yourself from those skeletons in the tenant and “why me” moments.

Let’s keep the late-night chaos for movies, not your inbox. Oh, and maybe keep an emergency stash of snacks. You never know what’s coming your way in IT. 

Also, try Syskit Point to stay ahead of the chaos; you’ll never end up on this list of IT horror stories.

With Syskit Point, get automated access reviews, detailed audit trails, and smarter data management, ensuring you’re always on top of things. No more last-minute panic or late-night PowerShell marathons.

Just smooth, stress-free IT management.