Wild Tech Support Tales

January 7, 2024 | Scott Mazza

Wild Tech Support Tales

Most of us have had to perform the unpleasant task of helping our parents out with a computer problem, whether it be an Internet connectivity issue or just trouble opening a file. But these tech support employees have seen a whole new level of stupidity.

1. White Knight Moment

For five years, I worked in IT consulting in a rural town about an hour's drive from Portland, Oregon. Occasionally, I'd handle fascinating, complex tech troubles customers brought in. One day, an intriguing woman walked in. She was attractive, around 40, with distinctive short blonde hair and vivid red lipstick, dressed like a character from a 50s advertisement.

However, she was distressed, spiraling into conspiracy theories that suggested paranoia. All ideas of engaging in friendly conversation with her promptly vanished. Despite this, I tuned into the conversation out of curiosity and a need for a break from my usual routine. What she told me was absolutely jaw-dropping. 

She was certain her husband was spying on her through numerous devices, driving our service technician to request my help. As the supervisor, I stepped in, assuring her that our experienced team would handle her unique situation. Up close, her stylish facade barely hid her deep anguish.

Typically, customers claiming surveillance are dissuaded by our investigative fees. But our team, specializing in computer forensics and data recovery, was trusted by the local department and various firms for expert assistance. We provided professional reports, supportive evidence for court cases, centering on family or marital disputes.

The woman insisted her husband was spying on her movements, her computer, and even within their home. She claimed he revealed this to her, threatening her should she tamper with the surveillance. Despite her attempts, she failed to secure a restraining order without solid evidence.

As a test, I proposed a discreet investigation by senior staff for $300 p/h, minimum four hours. To my surprise, she agreed, insisting to start with her vehicle for a potential GPS tracker. She was parked several blocks away, to avoid her husband's suspicions. Joining me were my colleague and our curious technicians. Here's where it gets interesting. 

Although GPS trackers are limited in their placement, our search revealed nothing initially. Then, I discovered a small device hidden behind the vehicle's front grill. This was not a real-time tracking device, but a system recording location data for a few days using internal storage and batteries. Bluntly, she was right to be paranoid.

Our focus shifted dramatically, acknowledging a dangerous situation. She had entrusted us with gathering evidence to help secure a restraining order. Seeing the GPS tracker led to tears, but she insisted more evidence was needed.

We planned to examine her home and computer for bugs, ensuring her husband wouldn't uncover our intervention. It was a week before the perfect opportunity arose. Meanwhile, our sympathies grew as she revealed more about her troubled relationship. Her genuine fear was evident, and I offered to lend her a firearm for protection, explaining the basics and ensuring she felt comfortable handling it. We parted with an empathetic hug, her worries for a moment shared.

As the date for the investigation approached, we prepared extensive plans. We arrived on the day with various tools, swiftly cloning her computer's drives for examination. I discovered SpectorPro, a surveillance software, monitoring every user activity. Meanwhile, my coworkers discovered two hidden cameras in her bedroom. We photographed and documented all evidence.

Later, we presented our findings to her for court use, waiving fees in light of her terrible situation. I wish I knew the final outcome, but I can only tell you that a week later, she appeared much happier. She was now living with her parents, a restraining order was in place against her husband, and she was filing for divorce. We had a touching moment of appreciation and relief—a reminder of the importance that our work can sometimes carry.

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2. An Analog Solution

I might not be in tech support, but since I'm pretty good with computers, my colleagues often need my help. Mostly it's basic stuff like "My Word isn't working", but once, I had a peculiar situation.

Colleague: I need help, I have to finish this document in 20 minutes but I can't type anything!

Me: What's happening?

Colleague: Whenever I press a key, Word just starts adding endless spaces between the letters.

Me: Interesting.

When I approached her desk, I instantly saw that something was off. I looked her straight in the eyes and, without breaking the gaze, I moved her phone away from the spacebar on her keyboard. She begged me never to mention it again. Obviously, within 10 minutes, the whole office knew about the incident.

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3. Oh, Vladimir

When I first joined my current job, there was a notorious customer known to all, only by his first name, Vladimir. Being new, my coworkers shielded me from Vladimir for the first few months until one fateful day, there was no one around, and I had to face the music.

I had no idea what I'd signed up for until I heard the operator's brief exchange with a fuming Vladimir right before he was transferred to me.

Operator: I'll be connecting you to our newest tech support person.

Vladimir: (Yells) I don't want a new one! I need someone experienced!

Operator: (Retorts) She's extremely capable, Vladimir! (She hands the call over)

Vladimir, although smart, lost his patience quickly and had quite the temper. It felt like he would often call not for help, but to vent about encountering issues with our product.

Yet, in our first call, my product knowledge allowed me to quickly address his issue once he quieted down long enough for me to explain the solution. Unfortunately, this led to me becoming his go-to for tech support. His mood swings were erratic but reading them became second nature to me—sometimes he needed a calm response, other times a fiery one so he'd listen.

Whenever I'd be talking to Vladimir, my one-sided conversation amused my colleagues. "Vladimir... Vladimir... Vladimir. Vladimir! You do realize I'm trying to help you, right? Do you want this fixed"?

Customer relations often reminded me of the TV show "House". I'd tell my techs "Customer's lie" (a reference to "Patients lie"). This rang especially true every time Vladimir called, as he constantly bent the truth to show how our product was failing him.

Once, when I instantly recognized a problem he was facing, the following conversation ensued:

Vladimir: I tried it all and nothing's working!

Me: No worries, I know exactly how to fix this. You need to do .

Vladimir: No, that won't work! I told you I've tried everything!

Me: (Puzzled) That's odd, it should work when you follow these steps.

Me: Can you show me exactly what you're doing?

Vladimir: I did everything you just said! Nothing worked!

Me: Can you please go through the steps one more time?


Me: Vladimir, please calm down. Can you try it just once more?

Vladimir: (Somewhat calm) Okay. I'll do it for you. I click here and... Oh, it's working! You're the best! You always know how to help when I call!

Years later, I was promoted to a managerial position and eventually stopped taking calls, which didn't sit too well with Vladimir. One day, amid multiple meetings on an actual urgent matter, the operator, on the verge of tears, informed me about Vladimir's tantrum because he was demanding to talk directly to me.

I was infuriated but busy. Finding a spare moment, I wrote Vladimir an email expressing my disapproval of how he behaved with the operator and explaining why his actions were hindering his own solution. I mentioned that his yelling had upset the operator enough to make her cry. Then, I went back to handling the urgent matter.

Shortly after receiving my email, the operator approached me with the following exchange:

Operator: Thank you for calling, how can I help you?

Vladimir: Is this the operator from earlier?

Operator: (Recognizes voice) Yes, it is.

Vladimir: This is Vladimir. I apologize for my behavior earlier. That was incredibly wrong of me.

Operator: That means a lot, thank you. So, need any assistance?

Vladimir: No, I just called to apologize. Have a great day!

Standing up for my employee and having Vladimir apologize was a proud moment. While I haven't personally heard from Vladimir in years, his escapades continue as he's found a new favorite tech support person. He still brings me up during his calls and continues his fabrication. Yet, there are times when I can still hear:

Vladimir... Vladimir... VLADIMIR! Will you just listen!

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4. Trust Me

I may not be an official tech guru, but for my family, I'm their personal tech whiz.

Grandpa: I can't get my computer to work and it keeps throwing up this weird error message.

Me: Let me take a peek at it for you.

Quickly Google searches the error message

Me: Looks like you've got some nasty viruses. I can install Malwarebytes for you and clean it up.

Grandpa: I don't want you tinkering around and installing stuff on my computer.

Me: Trust me, it's for the best.

Grandpa: Nah, I don't believe you. I'll just take it to Best Buy.

Me: But those guys aren't tech experts, they're sales folks.

Grandpa: You don't have a clue about any of this.

Surprise of all surprises, it was never repaired, caught more malware, and now it won't even switch on. He still won't give me the green light to wipe it clean and reinstall the system.

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5. Going Above And Beyond

Here's the thing: In IT, you avoid working on Fridays to escape weekend work if something goes wrong. To embrace that careful approach, we had a Friday tradition—4 pm happy hour. As the designated event planner, I arranged this happy hour, and on this particular Friday, I had just acquired an unlimited corporate account with the local beverage store.

We celebrated, and not in a restrained way. Our small company went all out, with drinks aplenty, cans piled up to the ceiling, and chips scattered around. Someone hilariously filed a chicken wing in the filling cabinet under "C" for chicken. It was one of those events where everything gets a little rowdy.

After five hours of merrymaking, we parted ways around 9 pm. I headed to a local bar to watch some bands play, relishing the end of the week with a pitcher of beer. But then a call came that left me nauseous.

I hurried outside to answer the call, stumbling up the stairs in the process. It was the CEO. Both our primary and secondary route servers were down. Our company depended heavily on these servers; they were practically the heart of our operations.

This was our first complete network shutdown ever. I was responsible for it, and I was less than sober. Amid the panic, I dashed towards work.

The severity of my intoxication dawned on me when I literally bumped into the glass entrance doors to our building. By the time I'd careened down a 20-foot hallway to get to the server room door, I knew I was in trouble. When familiar sounds failed to come from the card reader, I knew something was definitely wrong. No beeps, no recognition—a silent card reader, a dark screen, and a silent keypad. Nothing was working.

I was stuck outside the server room while our customers likely grew angrier by the minute. There was no way I was surrendering to the security system again, I was determined to enter that data centrer.

Having previously made futile attempts, I decided to take a different route—over the door. With the aid of a nearby chair, I lifted a ceiling tile and crawled in, forgetting to consider my lack of strength. I hoisted myself onto the slim wall beneath the suspended ceiling.

For clarity's sake, the suspended ceiling is a grid pattern supported by metal rods drilled into the concrete above, filled with weak, light tiles made from a mixture of cardboard and plaster. With nowhere else to support my weight, I resorted to clinging onto the rods while balancing myself on the grid's horizontal connectors. My plan was to drop onto the far side of the room, around 15 feet away.

The plan worked only for the first six feet. That's when disaster struck. I fell through a ceiling tile landing clumsily but on my feet. I dusted off, rushed to the security panel, turned the power off and on again and voila—it was back to normal.

The cause of the problem was a tripped circuit breaker that had knock-on effects due to a past electrician's faulty wiring. With limited time and resources, I cleaned up the mess caused by my ceiling entrance before heading home, content in fooling everyone into thinking nothing had happened there.

Come Monday, I was greeted by a flabbergasted co-worker and a dust-covered office. I had no idea what I had cleaned the previous day or how I had managed such a complex fault diagnosis under the influence. Yet, I had learnt a new way to bypass the security system—a technique I proudly added to our Tech Support Wiki.

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6. That Took A Turn

Two weeks ago, I was assigned a task: cut IT expenses from our budget by the year's end. The wider goal was to cut at least $3 million in companywide spending before fiscal year-end. I was even given a list of "possibles," a.k.a. people who could be fired if necessary.

Before resorting to layoffs, I decided to take a different approach. I called the team listed on the 'possibles' together and tasked them with studying our phone line and fax account usage for inefficiencies. They worked intense days and nights for two weeks to compile the data. The results were astounding. We discovered over 12,000 accounts connected to former employees which were still active, each costing $22.95 a month.

Our team then audited our fax system, locating inactive accounts. They stumbled upon over 37,000 inactive accounts. Some of these were never logged into, others belonged to previous employees, and a majority had set up their e-fax but never used it. A handful used their fax as an occasional backup plan.

By addressing these inefficiencies, we had already saved nearly $1 million per month. But I wasn't finished yet. I delved into vendor programs to hunt for identical wastage.

In our recent management meeting, the CEO reminded us of the need to make financial cuts by the year-end. After a lengthy speech, he had each department share their own cost-cutting strategies. The accounting and marketing departments both shared the ways they had been able to reduce financial burdens.

During the meeting, some departments surprisingly claimed credit for my team's auditing work. When it was my turn, however, I tabled how my strategy would make a significant budgetary impact.

Right before my turn, the CEO started to hint at wrapping up the meeting, but I interjected, emphasizing the importance of my report. I explained how my strategy had entailed increasing salaries by 20 percent to save bigger.

When one of the reps asked how more employees could save money, I explained how our created audit team was able to realize that there were over 100,000 accounts connected to different applications, services, and paid software that were no longer in use or were unaware of.

The CEO was sceptical about the meaning of all this, so I told him straight: we'd just saved an immediate $2.3 million. Pausing for dramatic effect, I clarified that this wasn't a yearly saving—it was monthly.

The CEO was flabbergasted at our unnecessary spending. He asked why this had been allowed to continue; I shifted the blame to his predecessor and underscored that we had now rectified the problem. I ensured him that no jobs were lost in this process, plus we even gained two new staff members in charge of managing vendor accounts.

In conclusion, we freed up an extra $24 million for company expansion—much better than firing indispensable employees.

Wild Office DramaPexels

7. Locked Out

I work for an after-hours help desk that offers basic tech support to a number of different businesses once their on-site IT staff have finished for the day. Many of these businesses are very far away from me, and I typically have little to no access to their internal systems.

Here's an example of a pretty silly call I received—it's pretty typical of what we deal with.

Me: Help De—

Caller: I can't get into the building, unlock the door!

Me: I'm sorry, you're contacting the IT emergency help desk. I can't unlock a door for you from this distance.


Me: Ma'am, this is an IT emergency help desk, specifically for handling major system failures or general after-hours tech support. As I’ve already said, I can't unlock a door for you because I’m too far away. Did you mean to call (I say the building address)?

Caller: YES!

Me: Alright, well, it's past 11:30 pm and the building closed at 9 pm. That's likely why it's locked.


Me: Did you clear this with management?

Caller: NO!

Me: Well Ma'am, without previous notice, the building would have been locked up by security as there's no record of you needing the meeting room after hours.


Me: For the last time, I can’t physically unlock the door for you from here, you need to converse with your management for further help. Also, this isn't an IT issue, and we currently have another caller waiting. I'll have to hang up.


Me: Alright Ma'am, as stated before, this isn't an IT emergency. While you're welcome to report this, we have other people in queue who need assistance. I'll have to end this call now, have a good night.

Caller: YOU FU—

Me: disconnect

For those curious, this particular business has not given us any emergency contacts for their security team. We're totally allowed to hang up non-IT-related issues, especially if there are other callers on hold waiting for assistance.

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8. Well, D’oh

Here's a story from my early days at my current job that I wasn't directly involved in, but got the interesting details from my mentor. A couple of days before a big holiday, we get a frantic call from a user whose equipment had malfunctioned, bringing production to a complete standstill.

I should mention that our company services equipment all over our country which is split by a sea into western and eastern halves—we're based in the west. This time, our client was a major oil refining plant. As our protocol goes, we started troubleshooting.

We asked—is this switched on? Is this connected over there? But the user kept responding with a "yes" to everything we asked, though the problem was not resolved. After about 30 minutes, our boss walks in. It turns out that the Head of Production at the client's side had called him, quite upset.

The equipment had broken down over an hour ago, severely interrupting production until it could be fixed. This was serious. The client was losing thousands every hour the production was halted, and they had all rights to sue us for damages due to equipment downtime.

The Head of Production was upset that their own team was unable to fix the problem and demanded that we send immediate onsite support. There were challenges—firstly, it was holiday season, and secondly, they were on the other side of the sea. However, they insisted to cover all costs for immediate support.

Here comes my mentor, tasked with fixing this emergency. He immediately packed his tools, rushed to the airport to catch the earliest flight. His wife helped him pack some clothes which she delivered to him at the airport.

Due to holidays, my mentor had to take an expensive business class flight. As he arrived, he was quickly taken to the refinery and given instant security clearance—a big deal in the petroleum industry.

About six hours had passed since the client's call. My mentor was met at the broken equipment by the Head of Production, the person who had called us, and other senior personnel.

Head: So, what is the problem?

Mentor: Wait, let's see. (Begins checking the equipment)

Mentor: Are you sure you've checked what I asked over the phone?

Client: Yes, I followed all your instructions!

Mentor: Sure?

Client: Absolutely!

Mentor: Remember the third thing I asked you to check over the phone?

Client: Why does it matter? Please just fix it!

Mentor: First, we make sure the equipment is turned on (points at the lights on the computer tower.)

Mentor: Second, we check if the machine is on (points to the equipment's light)

Mentor: Thirdly... (He turns a gas control valve and the equipment beeps.)

Mentor: ... we make sure that the gas is turned on.

Everyone went silent. My mentor calmly requested dinner now.

After an awkward silence, the head thanked my mentor and arranged dinner. Here's where it gets more interesting. post-dinner, my mentor checked into a hotel and the next day found that flights were sold out for the next four days due to the holiday. He called our boss who suggested he treat it as a paid holiday.

My mentor spent the next four days in a luxury hotel, enjoying a vacation paid for by the client, before heading back to work. We charged the client about US$10,000 for the flights, hotel, emergency arrangements and more—all for my mentor to turn a valve and check some lights.

Ignoring production losses, this story is a favorite of ours and always shared with new hires or clients. We often wonder what happened to the original client, but we know he was moved from his role not long after the incident.

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9. Catching On

Like most, my parents aren't exactly tech geniuses. But over the last couple of years, I've been working my tail off to make them (especially my mom) more computer-savvy. I'm a big fan of the whole 'teach a man to fish' routine.

Instead of just fixing every tech issue she encounters, we work through a process of figuring out what's wrong and how she might solve it.

Now, this can be super frustrating and time-consuming—sometimes taking up to an hour to fix a single problem. But, it's slowly starting to work. Case in point: my mom came to me with a tech problem today, which she had, as always, blown way out of proportion.

Mom: My phone's broken.

Me: What's going on?

Mom: The camera won't work.

Me: Can you be more specific?

Mom: I open the camera app, and it says no connection can be made.

Me: So what have you tried to fix it?

Mom: I've restarted it. Didn't work.

Me: Okay...

Then shockingly, my mom heads into tech jargon territory.

Mom: So I rebooted the phone in recovery mode.

Me: (astonished)

Mom: And cleared the cache partition.

Me: (still astonished)

Mom: But even after the reboot, it still didn't work. Looks like it's a bigger problem than I thought.

Me: ...

Mom: So I looked up similar issues online, most people said it turned out to be a hardware fault.

Me: How on earth did you learn to do all this?

Mom: I looked it up on Google.

Me: (jaw hits floor) So...your phone is really broken, huh?

Mom: Yeah. That's what I've been saying.

This is the same person who, two years ago, couldn't even adjust the volume on her phone. Now, she's troubleshooting on her own. Mom, I'm so proud of you. Welcome to the realm of admin privileges.

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10. A Big Mouse Problem

I ran a computer store and once helped out a county nature center by supplying and installing a campus-wide network across several buildings that were raised slightly off the ground. While we wired the buildings and installed the network and routers free of charge, we did ask them to cover the cost of the cables at wholesale price.

A year later, the nature center was experiencing sporadic connection issues which seemed to be worsening. They asked us to investigate, and we made a bizarre discovery. Rodents had chewed the cables in numerous spots. These issues took several hours to diagnose due to the small nibble marks, which were almost indiscernible upon visual inspection. Once we found the problem, we replaced the chewed wires, advised the center about their rodent problem, and billed them for the cost of the replacement cables.

One month later, the county's accounts payable department contacted us, accusing us of fraudulent charges. They offered us a choice: accept a one-year business ban with them or face a hearing, the outcome of which could result in a permanent ban and charges. I chose the hearing.

At the hearing, their IT guy alleged that our explanation for the problem was impossible. However, I pointed out that the invoice referred to a "bad mouse problem," which wasn't about a defective computer mouse but about actual rodents chewing the cables. This explanation was accepted, and the allegation dropped, but they said they'd be keeping an eye on us.

Tech Support Horror StoriesPexels

11. The Phantom Hand

This is how it went down last week:

Boss: You know, I had no idea we could print using our fax machine.

Me: Um, I think you're mistaken. That's just a fax machine, not a printer.

Boss: No, it definitely prints too. (He shows me some papers apparently printed from the fax machine). Look at this document. I printed it and it popped out from the fax machine instead of our printer. I was shocked myself!

Me: That's bizarre. As far as I know, the fax machine's just for sending faxes.

Boss: Then, where did these come from?

Me: Hard for me to say, but our fax machine isn't designed to print.

Boss: I'll show you. I'm going to print another document.

Me: Okay, let's see what happens.

After about 10 minutes

Boss: See, I told you. Our fax machine is finally printing. Although it took a while, it's printing the document I mentioned earlier.

Me: What? That’s not how it’s supposed to work. Let me have a look and figure out what’s happening.

I decided to print the log report from the fax machine and noticed the last few entries came from a Hong Kong number. Recognizing the number as our Hong Kong branch's, I decided to give them a ring. Finally, the mystery was unraveled.

Me: Boss, I've sorted out what's been happening with the fax machine.

Boss: So, you realized it doubles as a printer, huh?

Me: Not quite. Did you go to Hong Kong last week?

Boss: Yes, I had a few meetings there.

Me: While you were there, did you print anything?

Boss: Indeed, I did.

Me: And how did you arrange for your documents to print over there?

Boss: I connected their printer to my laptop.

Me: Have you checked that you're not still printing from that printer?

Boss: Why should I?

Me: Turns out, all your documents have been printing out in Hong Kong this whole time. Their secretary, thinking they were important documents, has been faxing them back to us!

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12. The Old Switcheroo

This story takes place back in 2001 during my stint at a medium-sized call center. Like most places, we needed a ticket for any IT problem, mainly because we supported about 500 users at any given time. Most users knew the drill and stuck to the rules, all except our rookie supervisors.

Many of these supervisors were in their early 20s and it was often their first taste of leadership. Suddenly, with an in-and-out tray and a personal stapler on their desks, they felt important. Liz, in particular, really embraced this newfound significance. Every minor problem would have her scrambling to call us and then physically running to our office when advised to open a ticket.

She'd insist, "I need this fixed immediately, I'm a supervisor". Most of the time, her issues could easily be solved with a few key strokes, but to get ahead of this recurring nuisance, I acted promptly whenever she called. I knew I had a few minutes until she turned up at our office, pounding on the door to continue her appeal in person.

Liz was undoubtedly an attractive individual, which meant that my young, geeky colleagues scrambled to assist her. Being in my early 40s, I wasn't as affected by her charm, and I used to resolve her issues remotely while she was on her way to our office.

I'd reluctantly follow her back upstairs to "verify" the already resolved problem. She'd often insist that it hadn't been behaving in that manner earlier and must have "fixed itself". After repeating this routine a few times, I finally told her, "Liz, I'm a happily married man and really, I'm just not into you. If you don't stop trying to corner me like this, HR is getting a visit".

After this, Liz began using the help desk properly, and my colleagues and I had a chuckle whenever one of her tickets landed in our laps.

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13. No Reply

Me: Hi, welcome to the Help Desk.

Caller: I need your help immediately!

Me: Of course...


Me: Yes, could you please describe the problem?


Me: Sounds frustrating. If it's an external company, we might have limitations. But let's try, can I remotely access to have a look?

Caller: Just get it done.

Me: Alright, would you mind showing me both the emails you've sent and those you've received...

The caller displays both her sent box with around 50 emails addressed to donotreply@.com, and her inbox filled with equal number of automatic replies telling her that she's reached an unmonitored account.


Me: Actually, you've been emailing a "do not reply" address. As you can tell from their returned emails. You probably need to use a different email address to reach them.


Me: Okay, can you follow my mouse?

Caller: YES!

Me: See this address in the "To" field?

Caller: uh-huh YES!

Me: What does it read?

Caller: donotrep...

Caller: oh...

Caller: hangs up

Well, goodbye caller. Hope your day gets better!

Immature adultsUnsplash

14. It Wasn’t Me

I once supervised shifts at an outsourcing company that provided software solutions to financial firms of all sizes. These institutions either used our development services or employed their own developers. A key part of our duty was handling physical backups. Each client had a unique backup schedule, and the backups were stored on IBM Ultrium tapes. Every morning, we had to replace the previous night's backup tape and send it to our secure storage site.

There was this one company with both live and test settings. They initially had daily backups, but their IT manager reduced the backup frequency for the test system to once a week as a cost-cutting measure. We updated our schedules and instructions to reflect this. Though I wasn't present when this happened, the details were passed on to our shift.

About eight months later, a developer from the company requested an urgent restore of a mistakenly deleted library on the test system from the previous night's backup. My technician informed him that the most recent backup was almost a week old, which meant they had lost nearly a week's work on the test system. The developer, displeased, demanded to speak to a supervisor. On the phone, I explained that the reduced backup frequency was a decision made by their IT department, not us.

Shortly after, I received a heated call from their Systems Manager, John Smith, who threatened legal action over the loss of their development work, accusing us of not performing the backups they paid for. In response, I explained that the backup frequency on the test system was reduced per a request from their own team eight months prior.

Taken aback, John demanded the name of the requester. After scanning our ticketing system, I found something that made me nearly burst out laughing. The original request was from none other than John Smith himself. Upon hearing this, John, flustered, claimed there might be another person with his name, though he failed to remember making such a request.

I offered to send over their email correspondence and the signed change form, adding that his requests could be found in his email's sent folder. John declined, saying he would notify the developers that the file couldn't be recovered. When I asked if he needed further assistance, he ended the call.

This incident, which I shared with my team and used for new hire training, highlighted the importance of thorough record-keeping.

Unreasonable workUnsplash

15. Unicorns Do Exist

A while back, I received what might be the best bug report ticket ever submitted. I had created a software that, under very specific conditions, would totally malfunction when it came across web pages developed in manners I considered utterly nonsensical. Unbeknownst to me, a lot of web pages out there are crafted in similarly illogical manners.

Then, one user happened to use my software on one of these bewildering HTML creations, and it crashed. Your average user, if they could ever contemplate going as far as actually reporting this glitch, would probably pen some comment like: Anticipated action: It operates. Current action: It doesn't. Steps to replicate: Check out a website.

I've come across way too many tickets of this nature. This user wasn't your "standard" user though. This fellow was a one-off. The bug report he sent contained a link to a small page on his own VPS that would trigger this glitch. He had enough awareness and had done sufficient testing on his own to craft a minimal example that still provoked it. That ticket is now printed and tacked above my workstation.

Tech Support Horror StoriesPexels

16. It’s All Downhill From Here

I got a request from a client who we handle IT services for. They're a marketing firm with specific needs and budgetary constraints, sticking to traditional tower computers. Their department head sent a ticket upset about the "unsightly boxes" and wanted them gone.

I thought it best to give a ring for explanation...

Me (On the Phone): Hi, IT Support here.

Department Manager (DM): Great, you're calling about picking up the boxes? Please make it within the next hour, we're off to a conference later.

They wanted 40 computers disconnected!

Me: Not exactly ringing for a pick-up... Rather to say, if we get rid of those boxes, your computers will be of no use.

DM: You think I'm clueless?

Me: Not at all, only clarifying that the computers won't work without being hooked up to these boxes.

DM: What?! I don't have to fiddle under my desk to use the computer. You clearly don't get what you're stating. Get me someone who knows IT. And I want your full name to lodge a complaint!

Me: Can't share my surname due to privacy reasons, but trust me, I am well versed. If the computer units, the 'boxes' you mentioned, are gone, your computers won't function.

The call ended abruptly!

I closed the ticket, after recording the events. A week later, we get an urgent call. None of their computers were operational. We discovered all the towers had been forcibly removed.

Me: Where have all the towers gone?

DM: I hired professionals to do the job! Told you it could be done!

Me: Not the point, now your computers are useless without them!

DM: Ludicrous! Just fix the internet so we can work!

Me: What happened to the computers?

DM: Are you daft? They're here!—indicating the monitors

Me: Right, the towers?

DM: They're junked

Me: So you're saying, you discarded leased computers, worth $1300 each? I need to talk to your boss. This instant!

DM: He’s busy in a meeting

Me: Need him now!

DM’s Boss: So, you dodge work and now interrupt my meeting. By the way, what happened to the computers?

Me: They've been junked, and we need to get them back immediately. They contain sensitive data.

DM’s Boss: Where are the computers?

DM: The boxes?

DM’s Boss: YES!!!

DM: They’re on the way to the junkyard

We raced to the junkyard, but found no trace of the computers. Two weeks later, a major data breach hit the company, resulting in significant losses, and pushing the company into administration.

Tech Support Horror StoriesPexels

17. Not My Problem

Back in my student days, I landed a summer internship as an IT Administrator. I was working on everything from helpdesk tasks to server-related tech, including offering user support in an automotive company, which dealt with airbags and seat belts among other things.

My workspace was a production facility linked to offices, providing tech support to both locales. One day, I got a call, which was unusual because we advise our users to send in tickets that we'd tackle in real-time and address within ten minutes. The call conversation went something like this:

"Goodness gracious, what are you doing with the scanners? The entire line is at a standstill, and we're stuck. They're down and showing errors". The location of the call was a 10 minute walk from my office, so I stayed on the phone as I headed over.

"Alright, tell me what's happening, just relax a bit"".


"Please calm down, we haven't touched that line for months”


At this point, I'm thinking of ways to deal with her but kept my cool. When I reached the spot, I asked her for a scanner. All the manufacturing line staff were standing around giving me disapproving looks. The team lead handed me the scanner and commented sarcastically, "Well, you messed up, now fix it”.

The scanner was straightforward; all it required was a username and password. I looked at the scanner's screen, then at her, back at the screen. I couldn't believe my eyes. 

"Did you get a prompt to change your password recently"?


"The screen indicates you've entered an incorrect password five times, and it's the standard rule that after this, the scanner locks for 20 minutes. By the way, you have three backup scanners, why didn't you use those? You made the mistake, not me. It's not okay to talk rudely to a company employee, therefore I'll report this to YOUR supervisor. We have call recording enabled on our phones". (we didn't, but she didn't know).

"Ugh… umm, umm".

"Alright, goodbye".

I reported her behavior to her manager. She officially apologized to the IT team, brought us some economy-pack cookies from the store, and made a show of being sorry.

Tech Support Horror StoriesPexels

18. Be Still My Heart

I've been away from work for roughly a month, so I haven't been kept in the loop about daily matters like building works and furniture rearrangements. So, when I walked into the office at 7:30 am today, it was quite the surprise when a facilities team member mentioned offhand, "The electricians plan to shut off the server room's power sometime today".

Talk about instant stress...

I made it clear that it's not as simple as flipping a switch in the data center. There's a proper protocol for downtime—it involves notifying people, ensuring the manufacturing departments in other buildings are prepared to continue work without access to job orders, and so forth. So, I started firing off messages to management, asking what on earth was going on.

Management suggested using the generator during the power outage. Being unsure myself, I rushed to locate the facilities manager and the electricians for clarification. After speaking with them, the electrician clarified they actually won't be shutting down power in the server room. They only need to cut it for part of the office. So, thankfully, the data center is safe.

You'll find me tucked away under my desk for the rest of the day, softly recovering from this nerve-racking ordeal.

Tech Support Horror StoriesShutterstock

19. Butterfly Effect

From day one at this little firm, I couldn't help but notice the terribly outdated workstations, edging closer to losing support and no longer holding value. So, I teamed up with a developer to tailor our internal software to run on brand new machines, a move I would later regret.

Jump forward roughly a year. Our project wrapped up and our application improved, processing tasks in a fraction of the time, from 10 to 40 times faster, based on the task. We upgraded everyone to shiny new systems that functioned smoothly, boosting our daily output. The department boss even sent out a praiseworthy email regarding the reduced processing time.

This team's workload began rapidly decreasing, to the point where the department head no longer needed to hire daily workers. Little by little, we had to let go of workers since there just wasn't enough work. Another year in, about 27% of our staff, around 20 people, were let go. Many of them were my friends. To this day, five years later, I still carry a sense of guilt.

Tech Support Horror StoriesPexels

20. Take A Load Off

Here I am, enjoying a quiet morning before things get hectic. I'm savoring my Dr. Pepper and indulging in a donut. For now, the queue is empty and my email inbox is silent. As expected though, the silence is broken by my ringing phone. I clear my throat, pick up the receiver, and greet the caller with a cheerful, "Hello, how can I assist you"?

"Good morning, my computer can't connect to the internet," the voice on the other end says.

Together, we go over some fundamental troubleshooting steps. I ask if the computer has been rebooted, if the cable is connected, if the indicator lights are on and whether the computer itself is on. Nothing works, so I find myself heading briskly down the corridor to investigate for myself.

Upon entering the room, I double-check all the things we had discussed on the phone. The cable is indeed plugged into the computer, the lights are on but intermittently blinking. Observing this, I start to trace the cable back to its source. The layout of the room is far from ideal, causing the Ethernet cable to be routed all around the room just so the person can place their desk strategically.

Following the cable, I discover it passes through a closet, exits the other side, and connects into the wall jack. I inspect the connection and notice the cable is taut, really taut. I can't shift it even an inch. As the caffeine from my Dr. Pepper begins to kick in, it suddenly clicks. I open the closet and there it is.

Hanging from the Ethernet cable are several coats, and they're not just lightweight jackets. They're heavy, bulky coats. The poor cable is under so much strain that it's tearing apart. I hastily remove the coats and explain to the person that an Ethernet cable does not double as a coat rack.

After removing the weight from the cable, everything springs back to life and I can finally return to my breakfast in peace.

Tech Support Horror StoriesShutterstock

21. Where’s My Money?

I work the late-night tech support for multiple companies including this certain university. At one point, I was in a call with one of the students;

Me: Hi, Tech Support.

Student: I can't print!

Me: Alright, can you explain what happens?

Student: I already said it! I can't print...

My patience is wearing thin, given the rudeness of the caller

Me: We've established that part. We need more info though. Are you seeing any error messages? What is the printer doing?

Student: It says I should top up my print account since it's at a $49 deficit


Student: are you there?!

Me: I apologize if I sound confused but it seems pretty straightforward. You'll need to settle your $49 deficit before you can use the printer.

Student: I don't have a debt with you!

Me: So, are you suggesting that this balance was mistakenly added to your account?

Student: Nope.

Me: I'm lost, can you explain what you meant?

Student: Yesterday, I photocopied a ton of personal photos and suddenly, I have to pay this. I don't think I should be charged since nobody told me about it when I was using the photocopy machine

Me: But... you do understand that photocopying isn't free, right?

Student: Obviously, I know that!

Me: If that's the case, then what's the confusion here? You've just admitted you knew that photocopying costs money. It doesn't matter whether you got a "warning" or not, you used the photocopier for a huge task, so now you have a deficit. It's simple: do a service, pay for the service.

Student: I just need to print, like, right now!

Me: In that case, you need to settle your account first by topping it up.

Student: But this is urgent!

Me: It's 11 pm. I'm not sure what you're asking here. To print anything, you'd have to clear up the deficit on your account first.

Student: I don't have a debt!

Me: You said you used our photocopy services, right?

Student: Yes.

Me: Do you have the photocopies you made?

Student: Yes.

Me: And yet, you haven't paid for any of them yet. Even your demand to "urgently" print something right now doesn't make sense. By your own admission, whatever you want to print doesn't have anything to do with your school work.

Student: I need to print a banner for a party.

Me: Oh, so just like your photocopies, these aren't related to your studies, which is a direct violation of our service policy. Plus, you're demanding all this from our IT emergency line as though it's all "urgent".

Student: Well, nobody warned me!

Me: Thanks for the call. I'll refer this issue to your university's administration for further examination. Sadly, I can't solve this situation on our emergency line. Goodbye.

Everyone Makes Mistakes At Work, But These Are UnforgettablePexels

22. Candy Crushed

As a Network and Server Administrator at a hospital, I sometimes answer help desk calls when things are slow. Once, I had an amusing call with one of our Switchboard Operators.

Me: IT speaking.

Operator: There's an issue I'm dealing with.

Me: Absolutely, what's going on?

Operator: I was playing Candy Crush on my smartphone, but it's continually giving me trouble.

Me: Could you be more specific? Is it that your phone is disconnecting from Wi-Fi, perhaps?

Operator: Not really. It's just that I can't seem to win at this stage no matter what I do.

Me: (Holding back my amusement) I'm sorry, but that's not an app I'm familiar with. Each department should have a Super User who can assist with app-related technical difficulties. Have you reached out to your Super User?

Operator: (Angrily) No, I didn't, wise guy!

Me: (Trying to keep laughter under control, like Jimmy Fallon on a Saturday Night Live sketch) I apologize if it seems I've upset you. I'm genuinely trying to direct you to the best help resource for your issue.

Operator: I thought you might be someone who plays the game and could provide help.

Me: I'm afraid not. Candy Crush isn't something managed or used by the IT department.

That was certainly one of the funniest calls I've taken. The humor came from the fact that the user was quite upset because I couldn't assist her and found the situation hilarious. I mean, really, who would expect IT support for Candy Crush?

Creepy StoriesShutterstock

23. Wearing Different Hats

Our headquarters includes some big meeting spaces. Despite not being in the event hosting business, we occasionally rent these out when they're not needed for our own purposes. We provide minimal services but make it affordable. It's fairly easy and brings in some extra cash.

This story revolves around such an occasion. A company that had rented our meeting rooms in the past booked them again, this time for a different event, so we had different guests on the scene. Our tech support was straightforward. We provide a quality projector per room, along with one HDMI cable, one audio cable for use with the room's speakers, and a Wi-Fi voucher for each device used for presentations. Anything beyond that is up to the customer.

This happened last autumn when both our IT and facilities teams had been hit by a wave of stomach flu. Despite having no official involvement with setting up meeting rooms for years, I lent a hand due to being short-staffed.

Typically, our head janitor arranges the room and our in-house catering assistant is on hand for guests, but both were out sick. I recruited Lucy, an intern from another department, to fill in. She was new, had only started a few weeks prior, and was open to the novelty of the job.

Understandably, Lucy needed guidance and support in her new duties. It took longer than usual, but we ensured everything was impeccably arranged in time for our guests. I advised Lucy to call me directly if the guests needed IT help before leaving.

As I was passing the conference area a bit later, I checked on the guests and Lucy. Everything was fine thus far: sound and projector were working and Lucy seemed confident in her role.

Thirty minutes passed and I got a call from Lucy. The guests wanted Wi-Fi vouchers. My bad, I forgot to brief her. I directed her to the front desk to collect one per device.

Ten minutes later, another call.

Lucy, seeming a bit uneasy: "Could you please come down here? The guests need help with the Wi-Fi…"

I felt something wasn't right, so I assured her that I was on my way.

Approaching the conference rooms, I could hear a woman's irritated voice berating someone heavily. Not good. I hurried, and found Lucy being cornered by a middle-aged woman in a suit who was yelling at her for not holding up her end of the contract.

Lucy was visibly rattled to an extent she appeared on the brink of a panic attack. I made my appearance known and confronted the woman, who was visibly and unapologetically upset over the Wi-Fi situation. She insisted that we hadn't provided the promised vouchers for all her attendees.

After enduring an unjustifiable amount of insults directed towards Lucy, I snapped. Lucy was just following policy and didn't deserve such treatment.

Unapologetic and even somewhat triumphant, the woman demanded to speak to a manager. I agreed to bring one.

I took Lucy with me and tried to reassure her of her excellent work performance despite the lady's harsh words. We headed towards my office. I took a moment to change into my more official attire, making a couple of calls and then returned to where Lucy was waiting.

In a twist of events unbeknownst to her, I revealed that I was the CIO of the company, hence the reason I helped her set up the room and I would handle this issue as the woman had demanded a manager.

We returned to the conference room where I allowed Lucy to announce my presence to the woman. The latter was clearly taken aback upon realizing who I was.

I clarified three things:

One: We'd provided the contracted Wi-Fi access for devices needed for presentations, not all attendees.

Two: Insults and intimidation were unacceptable on our premises; she owed Lucy and myself an apology.

Three: Due to violation of our agreement, including oversubscription of her event, she and her company were no longer welcome on our premises. Chaos broke loose.

Predictably, she put up a fight and was ultimately escorted off the premises by security. Her company faced the aftermath of her behavior and cooperated in an orderly manner.

A week later, we received a bogus claim of mistreatment requesting a refund. Our lawyer made light of this, countering with the details of the violations that led to her expulsion. We happily heard nothing more from them.

Tech Support Horror StoriesShutterstock

24. The Battery’s Low Upstairs

Someone approached me, complaining that they've been moving files for a while and it's only 61% done. I checked it out and guess what? They weren't transferring any files. They just plugged their video camera into the computer, and that 61% was actually the remaining battery charge on the camera. Turns out, they've been watching the battery level drop for hours.

Tech Support Horror StoriesShutterstock

25. Not So Useless After All

I was a project engineer at a modest-sized structural engineering company, dealing with about 10 other engineers and handling client inquiries once we'd sent out blueprints for their projects. We often worked on residential projects, which didn't usually give the construction engineers any hassle.

The main issue was when clients had trouble finding specific elements on the blueprints—anyone who's seen one knows that every inch of space matters. Good drafting is like a game of Tetris. But let me introduce you to a story's characters: Me, your friendly structural engineer, Big Boss (BB), the head engineer and my direct boss, and Incompetent Construction Engineer (ICE).

We were asked to do the structural design for some houses in a suburban development—hundreds of similar homes, minor changes here and there. We often try extra hard to save on costs as savings can quickly add up with this kind of project.

Sometimes we come up with solutions that are a bit unconventional. And so it was with this project.

ICE: One of the beams you drafted is collapsing.

ME: Are you sure? Can I come and take a look?

ICE: Of course, but we followed everything to the letter, I assure you, it's your design at fault.

Before we took to the field, my boss and I decided to review the project deeply, checking and rechecking every detail. We couldn't find any mistakes, so we prepared to defend our work. It's always the contractor's fault, right?

So, we geared up (helmet, visibility jacket, steel-toe boots), and off we went to check out the problem.

ICE: Look! The beam is sagging! We had to scaffold it, it was flexing too much!

It was clear, the beam was bending, which should not be happening. When we checked the blueprints versus what was built. That's when we saw the problem. One of our key columns was missing in both the blueprints and the physical construction.

BB: It seems like we missed out the column in the blueprints we sent, we messed up. Need to call our lawyer and insurance, it's our fault.

Still, I had a nagging feeling. I'd reviewed everything carefully, that key column had to be there in the blueprints. Usually, we sent a physical copy and a digital one, so I asked ICE to show me the physical copy. To my relief, the column was there in the blueprints we'd sent.

Now, who had made the mistake?

ME: There are discrepancies between the blueprints we sent and those you've shown us. Has anyone altered them?

ICE: Sure, I removed the column. It seemed unnecessary and costly. I even checked with one of our engineers who agreed it wasn't needed.

That confession was all we required. We went to ICE's boss and explained that unauthorized changes were made to our blueprints, and therefore, the fault wasn't ours. There was a construction engineer job opening the next day, and some workers got paid a little extra overtime to rebuild that part of the house.

Always trust a structural engineer. And remember, it's usually the contractor's mistake. It's refreshing to work in an industry where "The client is always right" isn't a hard and fast rule.

Tech Support Horror StoriesPexels

26. A Blast From The Past

About 15 years back, while I was still a tech-loving college student from a low-income family, I used to do freelance coding. I had this gig with a metal import business where I created a simple internal network program for them. It helped streamline their work, storing data in their accounting software.

Fast forward to 10 am this morning, I get a call out of the blue from the boss of that company.

Boss: We need you in town ASAP. Your program is down.

Me: I'm sorry? I don't recognize who's speaking. What program are you talking about?

Boss: Really? I’m talking about the program you developed for us.

Me: Oh...The one I developed a long time ago? You're still using that?

Boss: Yes, we are. But it stopped functioning this morning.

This conversation takes me on a walk down memory lane. But I shake it off quickly and try to problem-solve. I've kept copies of all my work, even my earliest codes. Just because a program is old, doesn't mean it stops working all of a sudden. I try to pinpoint the problem—was there a power outage? Any changes in the network? A hardware malfunction? But everything checks out.

I can tell this is going to take some time.

Me: Look, I can't fix this from here. I doubt it's my code, but to ensure that, I'll send you the source codes. Maybe it's a hardware issue. Save some money and get someone local to take a look.

Boss: Pay you? Why would we pay you? It's your code. You need to fix it.

Me: (laughs) Well, I wrote that code 15 years ago, and it's been running smoothly until now. Even big corporations have a cutoff for support. For example, Microsoft doesn't even support XP anymore. So, it's unrealistic for you to expect free help from me.

Boss: We still want you to fix it. What's your cost?

Me: I'm employed elsewhere now. I'll have to take time off, unpaid, to help you, and you'll have to cover all my expenses in addition to my daily rate. But I doubt I'll need more than one day.

Boss: That's too high.

Me: I understand. That’s why I suggest you get a local technician to check it out. If the issue is with my code, I'll gladly hand over the source codes and you can have them updated as you like.

Boss: I don't get why we need to pay after all this time. It's your program. You need to provide the support.

Me: Well, things don’t work that way. Anyway, I'll be here waiting for your call from this number.

He ended our call still grumbling about how I should be the one fixing the issue for free.

Now, I'm daydreaming about what the future holds.

Revenge Stories factsPixabay

27. That’ll Be The Problem Then

Me: I'm part of an internet service company that only provides DSL-type connections. We don't offer services for satellite, mobile, or anything else.

Customer: Hi there, what happened to my Wi-Fi?

Me: Hello sir. Could you please clarify your issue?

Customer: I’m using your service and recently, I've been having problems! I haven’t had Wi-Fi for about a week now! I normally see it on my phone. Where did it go?

Then we troubleshoot the problem for about ten minutes, until…

Me: Based on what we've checked, the wired connections appear to be in order. The problem might be the Wi-Fi feature of your router. Do you have an extra router we could use to confirm this?

Customer: Yes, but I won't be able to change them at the moment.

Me: May I ask why?

Customer: Because I'm not at home currently.

Me: Oh, where are you then?

Customer: I’m in Mozambique.

Tech Support Horror StoriesPexels

28. Black Out

After I recovered from a stroke, I was really eager to get back to work. I was so eager, I even jumped at the chance to work an overnight shift at a webhost doing tech support. Most of my nights were quite smooth with callers needing more help to enhance their websites rather than fixing them. Such interactions were a nice way to break the silence of the shift. Every so often, I would encounter an interesting situation, like this one.

One call I received was from a frantic guy. After calming him down and verifying his username and password, I asked him which of his websites was down. I keyed in the URL on my browser and voila, his website was working fine. I did a bit more checking, but still couldn't identify any issues.

Our next step was to troubleshoot his computer.

Me: Okay, are you using a Mac or a PC?

Customer: PC

Me: Can you please open the start menu and type in CMD.

In the next moment, the root of his problem was glaringly obvious.

Customer: I can't. My screen is black.

Me: (Taking a deep breath) Can you see any light on your monitor or computer tower?

Customer: No

Me: (Taking an even deeper breath) Is the power cord properly inserted in your device and the wall socket? If you have a power strip, is it switched on?

Customer: (Rustling sounds) I think so, but I can't seem to tell.

Me: What do you mean you can't tell?

Customer: I just can't see. It's really dark.

Me: Dark? Can you turn on a light?

Customer: I could use a flashlight, but there's no power.

Me: (Fortifying myself,) Don't worry sir, your website is live. Please check again once your power is back.

Petty divorceShutterstock

29. You Get What You Pay For

As an IT Hardware Support member at a college, nothing grinds my gears more than a lack of communication. Picture this: one morning, as I was entering the campus, my phone buzzed with an incoming email. Taking a quick peek, it read: “We've just received fifty new laptops. Kindly install the latest Windows version along with several softwares (list followed), and have them ready by 10 am tomorrow". No ticket, no purchase order information, nothing. I was blindsided.

My boss was just as clueless; he hadn't received any request for new laptops. After failing to reach the department over the phone, I decided to walk over and assess the situation. At the department, I found dozens of boxes in the middle of a classroom, within which were 7-inch Windows tablets with attachable keyboards: budget tablets with barely enough memory to run Windows 10, let alone handle the software they requested. I knew we were in big trouble. 

Understandably, this was daunting. I asked how these were ordered without going through the usual channels, only to discover they had bypassed our system for a "better deal". They were adamant about having everything set up by the next day.

Back at the office, the grim revelation to my colleagues and boss about the department’s new "toys" didn't go down well. It was impossible to install the required software on these tablets or even connect them to our network for student logins. After explaining this to the department head, we suggested they return the tablets and offered to provide suitable alternatives. Unfortunately, the tablets were non-returnable and purchased directly via a department credit card.

Stuck with an unusable fleet of tablets and a department head demanding answers, we scrambled for solutions. We decided to connect the tablets to the Wi-Fi network and create generic user accounts for each tablet.

Despite being delivered a week later than intended, the struggle didn’t stop there. On the first day, a ticket came in reporting Wi-Fi connection problems. I found that the class was trying to connect using a single shared username, which was listed on the board, ignoring the printed login instructions right beside it. Furthermore, charging issues surfaced due to the sensitive connections of the device which had to be positioned precisely to charge. Naturally, errors occurred.

Despite all this, we still receive occasional requests for software installations on these tablets. To top it all, the students are disenchanted with the tablets because of their tiny, child-like keyboards. The whole process has been exasperating and I wish we had a more centralized purchase system for all computer requests.

Tech Support Horror StoriesShutterstock

30. Know Who You’re Firing

Back in the early 90s, around 1993, I was managing IT systems for a medical transcription company. Our work was groundbreaking at that time, as we were remotely printing transcriptions in hospitals, among other things. Things were running smoothly...until they weren't.

Being the sole IT guy in town had its drawbacks—I was on call all the time and surviving on about 3 hours of sleep. Most of my time was spent juggling between napping and troubleshooting issues at the hospital.

Then, the company dynamics changed when two VPs moved to our city a few months in. After using a flimsy excuse to fire our director, they took over things themselves. My workload expanded to maintaining doctors’ computers as well.

Fatigue and frustration were catching up, so I started job hunting. One particular exhausting day, I was sent to a hospital to fix a printing issue. I hadn’t been home for two days and had been awake for 18 hours straight.

Upon arrival, the solution was as simple as plugging the modem back in. A doctor approached me, stating that I was also expected to fix his home computer, an expectation set by the VP. I had to turn him down politely and told him I needed some sleep.

When I got to the office to grab some stuff before heading home, the two VPs and the office manager gave me quite a dressing down. My response? I chuckled. I mean, I was the only IT literacy within a thousand miles radius. They lost it and fired me on the spot. I assure you, I genuinely thanked them.

Ironically, it was my son's birthday, December 15th. On the way home, I dropped off my resume at a local computer store. They had no vacancies but would consider my application. Worried about breaking the news to my girlfriend, I went home only to find her message blinking on the answering machine. The computer store called—their main engineer just quit, and they wanted to know if I was still interested. I assured them I'd be there by tomorrow.

This was the start of a far more relaxed and satisfying IT career, with better pay, shared on-call responsibilities, and a ton of holidays. And to top it off, the transcription company fizzled out. The VPs got sacked, the company struggled for a bit, and was eventually bought out by a competitor.

Teachers Got Fired FactsShutterstock

31. Catching A Big Fish

A couple of years back, I got an invitation to take on a part-time gig. I usually have something on the side, but at that moment, I didn't. It was from a guy I vaguely knew who lived about four hours away. We chatted online and it sounded like a good gig—he wanted me to write some software for his shipping/warehouse business. He even offered to cover my travel expenses if I could meet him.

When I arrived, the situation seemed somewhat sketchy, but I chalked it up to him being a new, underfunded small businessman. I decided to follow it up despite my reservations. We met up in a restaurant. After discussing the job details, which I'd already heard before, he then insisted I meet his client before anything could proceed—apparently, the client needed proof of my abilities.

Prior to our visit, he instructed me that no matter what he says, I should've asked him any questions later. During the meeting, he introduced me as his employee instead of a contractor, which didn't sit well with me. He explained later that he didn't want his client knowing he was outsourcing. I should've run right then. 

Eventually, we agreed on the terms of the work and payment. His method was far from simple but acceptable. It involved daily uploads of my work to the cloud and a record of my working time. Payment was to be done biweekly.

This went well until the first time he missed a payment. I reached out and continued working. But after working for a week in arrears (the equivalent of the advance he gave me), I stopped uploading my work. After getting paid, I resumed uploads. However, he later accused me of charging him for the days I allegedly didn't work because he delayed pay.

In the following period, he missed yet another payment. This time, I refused to work or upload until he paid me the full amount, despite his insistence. Shortly after, he called me, desperate for help. He explained that the company's systems had been crashed by a disgruntled admin who had been recently fired. This was a huge issue since the admin had used unlicensed operating systems. After this hilarious revelation, I realized that cutting ties with this company was a good thing.

But it didn't end there. Weeks later, an FBI agent called me on a Saturday morning. I was being questioned over the system compromise at the company. It was then I realized and explained why they wouldn't have had any monetary losses from the incident. They didn't own the operating systems. Finally, the drama was over (Or was it?).

Awful RelationshipsPexels

32. Mystery Solved

Twenty years ago, a seasoned systems administrator shared an older story with me, so it likely occurred in the 80s or early 90s. The setting's a factory that produces heavy machinery. Modern for its time, it had floor terminals linked to a mainframe computer for tracking parts and other necessary tasks.

One day, a systems admin gets an unusual call from the production floor. After the usual greetings, the caller claims, "I can't log in when I stand up".

The admin initially thinks this is just another run-of-the-mill issue. He asks the usual questions: Is the power on? What's showing on the terminal screen? Forgotten your password, perhaps?

Interrupting, the caller insists, "I know my stuff. When I sit, I log in just fine, but standing up doesn't work".

The admin tries to make it clear that there's no possible connection between standing or sitting and the login process. Despite a protracted phone conversation, the user doesn't budge. So, the admin makes his way down to the factory floor to demonstrate the absurdity of the claim.

Sitting down at the terminal, he receives the password from the user, logs in, and shows everything works fine. He tells the user, “See? Your password works as it should”.

The user replies, “Just as I told you, log out and try again, but this time standing up".

Humoring the user, the admin logs out, stands, types the password and—surprise—it comes back as invalid. He tries it again, same result. Perplexed, he tries his personal mainframe credentials standing—again, invalid. Sitting, he logs in successfully. Suddenly, this "crazy" user's anomaly becomes a captivating debugging riddle.

News spreads—there's a terminal where sitting or standing impacts password validation! The factory’s high-tech workers, eager for a fun debugging challenge, gather around. Production screeches to a halt as everyone wants to test if they're also affected.

Most people aren't, but there are a surprising number who can't log in while standing, and some who can't log in regardless of position. After much head-scratching, they discover the truth. A prankster had swapped two keys on the keyboard.

Both the original user and the admin had one of these letters in their passwords. They could comfortably type while sitting, not needing to look down at the keyboard. Standing, however, was unfamiliar, causing them to glance down and hence press the wrong keys.

Some users, who struggled with typing, couldn't log in at all. For others without these letters in their passwords, the swapped keys never caused a problem.

Tech Support Horror StoriesShutterstock

33. Taking Me On A Journey

Me: Hi there, Retail IT. Daniel speaking.

Caller: Daniel, I need your help. I'm a district manager with a presentation in 15 minutes and my laptop's crashed. I'm really panicking and don't know what to do.

Me: Uh-oh. Sounds serious. I'll need to get a systems technician to give you a ring and help you out.

Caller: Any chance you can help me out? I hate to be that person, but I'm seriously stressed right now and time is of the essence...

Me: Alrighty, could you tell me what's happening with your laptop?

Caller: It's not turning on. It showed a blue screen and just turned off by itself and now it won't power back on...

Me: Yikes. That does sound bad. We might need to consider a laptop replacement...

Caller: Oh no....(starts crying)

Me: Hang in there...

Caller: I've been on this presentation all week! I can't believe this is happening (starts sobbing)

Me: Stay calm, alright. We'll figure something out.

Caller: (keeps crying)

Me: So, I'm guessing the presentation you've been working on was on PowerPoint, right?

Caller: Yes... (sniff)

Me: Was it saved on a network drive or only on your computer?

Caller: I'm not really sure. I think it was just on my computer...(sniff)

Me: I'm pretty confident it might be saved on the network drive, and you just weren't aware.

Caller: Alright.

Me: I may need to sift through numerous folders. Could you tell me the name of your presentation?

Caller: Yeah sorry, it’s (he tells me).

Me: Alright, let's take a look. Found it!

Caller: Are you serious?.....(sniff)

Me: I’ll save it now and then email it across to you. Do you have a phone or iPad by chance?

Caller: I've got both!

Me: Great. Are you currently in a meeting room?

Caller: Yes, I am.

Me: Perfect, does the room have Wi-Fi?

Caller: Yes... I believe so…

Me: Excellent. Try to find the Wi-Fi and connect your iPad to it.

Caller: Okay. I'm receiving emails. I can see yours......Oh my gosh......OH MY GOSH!!!

Me: Voila! I'm not sure about the setup in your meeting room but usually, there's a way to project your PowerPoint from your iPad to the screen.

Caller: Oh gosh... (crying) I can't believe it, you saved me!

Me: You're welcome. Just glad I could assist.

Caller: Please expect a hug and a drink from me next time I'm at the office!

Me: Sounds like a deal. Hope your meeting goes smoothly!

Caller: .........................

Me: I'll take your silence as a goodbye then?

Caller: Hahahahahahah. Guess what... My laptop just came back on...It wasn't plugged in and I suppose the battery died. How silly of me…

Me: …………………………

Caller: Hello?

Me: (Can’t help but laugh/cry).

Tech Support Horror StoriesShutterstock

34. Never Say You’re Sorry

My client sent me a PSD file, asking me to convert it into an HTML file. The PSD was set at a width of 600 pixels. After working on it, turning the live text into HTML, uploading the page to the server and sharing the URL, she emailed me in a panic. Our conversation unfolded as follows:

Client: This is awful! Everything is much bigger. It doesn't match the PSD I gave you at all.

Me: Can you elaborate on "much bigger"?

Client: It's really enlarged! You need to rewrite the code to mirror what I sent you.

Me: (Totally puzzled) Could you help clarify the issue by sending a screenshot?

Client: (Sends a screenshot of Photoshop and Safari side by side. There's no difference)

Me: From where I stand, they look identical, both with a width of 600 pixels. I didn't modify the PSD in any way.

Client: (Skilled enough to employ "inspect element" on Safari) Fine, it's 600 pixels, but why is it blown up?! This is not okay. I'll get someone else to rewrite this.

Totally stumped, I revisited her screenshot, this time noticing that her Safari was set at a "33%" zoom. Apparently, she was at 300% zoom on her Safari but she'd downscaled the screenshot to fit on the screen (which defeated the purpose of her sending it).

Me: Could you double-check the zoom level on your Safari browser? Your screenshot suggests that it might be the problem.

(No response)

Much later, she contacted me again about a different project, completely ignoring the earlier issue.

Me: By the way, was the previous project approved?

Client: Yes.

No apology, no acknowledgement of the oversight. It's confusing how she knows about pixel width and how to inspect photo properties, but still flounders in situations like this.

Tech Support Horror StoriesPexels

35. All In A Day’s Work

My buddy got a Netflix box for her TV but ran into trouble setting it up, so she asked me to help. I couldn't get over there until after work, but by the time I arrived, it was working fine. She told me she had called Google for help, which confused me because the box wasn't a Google product nor did it rely on any Google services. I assumed she had just googled the manufacturer's number and they sorted it out.

To prove my point, I decided to check her caller ID. I couldn't believe what I saw. I was stunned when I saw it really was Google. Turns out, a tech support guy from Google had spent a good chunk of time on the phone helping her set up an unrelated product, all for free. Well, it looks like Google is truly a handy service.

Tech Support Horror StoriesShutterstock

36. Burn It To The Ground

I've never been in tech support. No job I've had ever required me to help with tech issues. But life has a funny way of giving you a curveball. As someone who often worked night shifts and spent time with the IT crew, I became an unofficial tech assistant. This worked out pretty well for the team because they could relax at home during their on-call shifts while I handled minor issues on-site. It also gave me something different to do besides my usual desk work.

Fast forward a few jobs, and suddenly everyone's talking about "business intelligence", "data analysis", and "data-driven decisions". These became popular topics in the corporate world, but ironically, none of those tasks were included in my job description. Yet, I found myself dealing with large amounts of data and crafting detailed reports.

Call me lazy, but if I have to do the same task twice, I find a way to automate it. My 'lazy' solution was a somewhat organized PowerBI dashboard on SharePoint—a mess, but a functional mess. It drastically reduced my team's report generation time from a week to just a few hours each month, which was a major win.

Besides my usual duties, I found myself taking on the roles of a BI developer, data analyst, and casual tech assistant. When negotiating my salary hikes, I always pointed out these added responsibilities to justify a higher wage. Yet, each time the company would resist my demands, making the whole process rather uncomfortable. Fast forward a few years, the company decided they didn't need me anymore but instead needed someone to maintain the systems I had created. I was told I would be laid off in 60 days.

Ensuring everything was in order and ready for my inevitable replacement was my top priority. There was just one problem. They couldn't find a replacement who could handle my unique "three roles in one" situation. On my last day, my boss asked me to delete everything from GitHub due to security concerns. Despite my best efforts to explain the importance of preserving the data for my successor, I was ordered to wipe it.

A month after leaving, my old boss called asking for help. They hadn't found a replacement yet and needed help. I agreed to assist, asking only for a steak dinner for my troubles, which were far below the contractor's rate living in the area.

A couple of days later, I returned to work and began searching for my backup folder on OneDrive, but it was missing. My former boss informed me that they had deleted it, mistakenly thinking it was unimportant. Those files were the fruit of hundreds of hours of work, and a restart from scratch would simply take too much time.

I left the meeting empty-handed without my steak dinner. Days later, they called me again, asking how much I'd charge them for a new dashboard as some high-ranking corporate executives overseas missed the charts for their presentations. That's when I started working my magic, pulling out a relatively old version of the Git report that I conveniently had on hand. I didn't mention my lucky find to them, and instead bumped up my hours as if I were starting from scratch.

How Affairs Start factsPixabay

37. That One Didn’t Land

I work at a surgery center, and so does Sandy, an incredibly sweet but somewhat naive older woman who operates the switchboard phones. Let me tell you a story about the time I updated Sandy's computer, and by accident, made her cry.

Me: There, it's all set. Any questions about your new computer before I move on to other tasks today?

Sandy: But how do I use it?

Just to give you some context, it was an unusually hectic day and I'd made a blunder of not providing her with a keyboard or mouse.

Me: Actually, these new machines don't need a keyboard or mouse. They connect straight to a harmless neural implant which creates a truly cordless experience; the whole process only takes roughly 45 minutes. You're scheduled with Dr. Smith in operating room seven at 12:15.

Sandy: Wait... I...

At this point, Sandy's eyes widened and she started crying.

Me: Oh no! I'm so sorry! I was only kidding! I had just forgotten to give you your keyboard and mouse. There's no such implant, it was just a joke. Please forgive me! I'll get your keyboard and mouse right this second!

This event happened a long time ago, but it still tugs at my heart. Thankfully, she calmed down and even found humor in it a few minutes after I clarified it was all a joke.

Instant Karma factsShutterstock

38. That’s Between You And Your God

I have a challenging client who probably shouldn't be involved in hiring web developers.

He rings me up, not pleased:

Client: "Hello! I had the idea that this website would be functional on a laptop"!

Me: "It is. It's a website".

Client: "So if I open a laptop right now, are you saying it would run"?

Me: "Exactly... As I mentioned, it operates on a laptop".

Client: "How on earth would you know that"?

Me: "Well, my reasons are: 1) I created the website, 2) I'm not a novice, and 3) I OWN and USE a laptop"!

Client: "You possess a laptop"?!

Me: "Yes! You've even seen it. It's my primary computer"

Client: "And it functions"?

Me: "Indeed"!

Client: "That's cool"!

Me: "Do you own a laptop"?

Client: "No".


Client: "Should I buy a laptop"?

Tech Support Horror StoriesShutterstock

39. Karma Comes Back Around

A couple of years back, I was dispatched to our branch in Italy to assist the local IT squad in training their new IT support guy on running his help desk tasks. Everything was going smoothly. One day, we all decided to try a local Italian delicacy—a Turkish Kebab.

Once we arrived at the kebab shop, I started examining the menu with my team's assistance. Fortunately, the guy serving us spoke English and was eager to brush up on his language skills. We began a casual conversation as I ordered my "AwesomeKebab".

Curious, he asks me what brings an English speaker to Italy. I unknowingly walked into a trap by casually saying I was handling "IT Stuff". Fast forward about 15 seconds and I find myself with an old, worn-out laptop running on Windows 7 with a Turkish operating system that couldn't function.

While he was preparing my meal, I decided to help him out. When my kebab finally arrived, I delicately nibbled on it for nearly 20 minutes. I tried valiantly, using context clues and experience, to diagnose the issue based on his vague description that "something was wrong with his internet connection and it wouldn't work".

Eventually, I determined that his network card seemed to be faulty and suggested he should consider reinstalling it from the original installation disks or resorting to a wired connection for the drivers if needed. He seemed content with this solution and brought our bills over.

As he was rounding up the table collecting payment, when he got to me he warmly declared, "Not you my friend, today, your meal is on the house"! Unexpected tech support was definitely worth the complimentary kebab.

Tech Support Horror StoriesPexels

40. Oops, My Bad

I received a text from a friend telling me that someone they knew needed to replace a broken laptop screen. They already had the new screen, they just needed it installed. So, I got in touch with this person, and he asked if I could come to his job to fix it. I agreed. However, I needed approval from his employer. Lucky for me, he actually owned the business.

The following day, I arrived at his office and he handed me his laptop. He led me to a vacant desk in the accounting section, where I successfully replaced the laptop screen. He was in a meeting, so I spent my waiting time in the accounting sector. There, I observed two older men laboring over an excel spreadsheet. It was a tedious task of reading and calculating vast arrays of numbers, and they'd restarted twice.

I decided to step in, ready to revolutionize their workflow. I thought was about to blow their minds—I was really about to ruin their lives. I introduced myself and showed them how to utilize Excel's automatic calculation feature. Explained that, with this, they could complete a task in minutes that would normally take them hours. Suddenly, amid my training session, I heard a sharp "You're all fired for incompetence".

The company owner had been standing in the doorway, eavesdropping. After the shock wore off, he revealed to me, "I've been waiting for that spreadsheet for two days. You sorted it out in less than a minute". He courteously handed me $200 and since then, has been referring numerous jobs my way.

Lazy People factsShutterstock

41. A Bunch Of Morons

I run a small IT business in Georgia. I used to be a top-notch technician, but my role has shifted to a more meeting-oriented one. However, I like to keep my skills sharp by troubleshooting an issue here and there.

Recently, our system monitoring flagged a lot of failed login attempts from one of our major clients. This typically signals that someone is trying to forcefully gain access, so it's something we pay attention to.

Generally, we have the warning set to a low level and most of the time it's just shared computers causing the alert. But this time was different. It's a fax server at a smaller, remote office triggering the alert. Since not many people use fax servers, I decided to personally look into it. When I tried to remotely login, the system kept looping at the login screen.

Suddenly, before I could put in the password, it tried to log in by itself. Huge red flags! After observing more failed attempts, I knew a bot was trying to breach the system. It didn't make sense why someone would target this particular server that isn't as vulnerable as others.

I pulled in two of my experienced techs to figure out the source of the attack. To be safe, we didn't want to log in in case there was malware capturing keystrokes. Instead, we used backend commands. But things just got stranger.

We were unable to trace any external attack on this machine through the firewall or switch. One of my techs suggested that there could be malware on the server itself, trying to jam its way in to eventually report back once it gains access. We decided to quarantine the machine to confirm this suspicion.

True to our hunch, the attack persisted even without any external input. But it felt off because if the machine were indeed compromised, there are more efficient methods to get passwords. Could this be an amateur mistake? We sifted through active processes but found nothing suspicious.

Nonetheless, something was causing this, so we started to shut down the most suspicious processes without success. In desperation, we decided to physically retrieve the server.

Meanwhile, I informed the clients' management about a possible breach, and our investigation was ongoing. Just as a tech was en route, the failed logins stopped. The last process we terminated seemed to have made the difference.

But it was a significant server process, which got me panicking about the potential vulnerability of hundreds of servers relying on this particular process. After restarting the server, things went silent. We created a temporary admin account and started to dig into security logs for any clue.

The peculiar part? All failed login attempts were through our admin account, and they originated from the server itself. Usually, attempts come from various common user names and overseas IP addresses, not from the local machine.

Just as our tech reached the remote office, we stumbled upon the answer. As he arrived, the receptionist complained about a beeping machine, pointing out the fax server. Approaching the server, our tech noticed a catalog on the enter key, removed it, and informed us that we've been on a wild goose chase.

Dirty little secretShutterstock

42. The Harpy Rises, The Harpy Falls

I've been steadily climbing the career ladder at my current IT company. The way I interact with clients is similar to how I treated customers at Starbucks: with kindness, understanding, and empathy. This approach has really helped me build strong relationships with all the clients I have dealt with.

Specifically, there's one mid-sized regional company that I assist with, although they aren't my primary concern. This company offers ambitious individuals the chance to significantly profit at the expense of those who might not have the same strength of will. I'll leave it up to you to guess what industry they are in. Let's refer to them as SlimeCo.

While some of the people at SlimeCo I deal with aren't the most pleasant, many are actually quite nice to me. I show up, do my job without overpromising, and get things done, which differentiates me from the other techs there who constantly fail to meet their ambitious deadlines. However, there is one woman at SlimeCo who is an absolute nightmare.

Picture the couple from that Kitchen Nightmares episode where the wife is absolutely convinced she can do no wrong and believes everyone is out to get her. That's this woman to a tee. She's a constant problem for everyone, and my usual friendly attitude doesn't phase her because in her mind, I'm just out to ruin her life.

I generally avoid her as much as possible because I don't have the time or energy to deal with the countless tickets she raises about the same timeless issues. We'll nickname her The Harpy from now on.

So, it’s 4th of July, and I'm out enjoying my friends' cottage when I get a call at 2 am from a number I don't recognize. I thought it might be an emergency, so I answered it.

It started out innocently enough, with me answering the call a bit sleepy and bewildered. Then Harpy reveals herself, complaining about her persistent laptop issues. When I questioned how she got my personal number, she dismisses it and demands a fix for her laptop.

I told her that I wasn't on-call, had no internet access, and SlimeCo was officially closed until Tuesday due to the holiday. However, she didn't even batting an eyelid and kept insisting that I find an internet connection to fix her laptop immediately.

It was clear I wasn't going to get anywhere with her, so I told her to submit a ticket and I would handle it. After she hung up on me, I switched my phone to silent and went back to sleep. When I woke up in the morning, I found 61 missed calls, 14 voicemails, and over 200 emails from the Harpy.

I decided to block her number and the next day, my boss experienced a similar issue with her incessant calls and complaints all night. As a result, a complaint was filed against Harpy and a host of other actions were unleashed.

That's when we discovered the twisted truth. An internal investigation revealed that the Harpy had gotten my number from the CFO’s unattended Blackberry, which constituted a grave security breach. My boss informed me that we were severing our contract with SlimeCo.

Two hours later, we found ourselves with SlimeCo's management and our legal teams renegotiating a new contract with added security precautions. Amid all this, SlimeCo proposed a 'settlement' to dissuade me from proceeding.

In a surprising turn of events, SlimeCo cut a check to pacify me, placed Harpy on probation, gave me a week off on their dime, and released me from providing any further service to them. It wasn't what I anticipated at all, but a welcome resolution nonetheless.

Dumbest peopleShutterstock

43. I Want University

I'm employed as a student IT assistant at my college (don't ask which one). Part of my job is supervising the computer labs open to students. Since it's summer as I write this, it’s only a light trickle of students. However, a few weeks ago, I encountered the least tech-savvy, most bewildering person I've ever had the challenge to assist.

One day, I was manning the help counter when an adorned blonde woman, mid-20s or so, walked in. As she sat down at a computer and shot me a panicked glance, I had a feeling she'd need some help.

Predictably, she soon called out loudly, "HEY, I HAVE ISSUES". I tried to coax a precise problem out of her, but she insisted I come over to her station. I regretted indulging her as she was waving her mouse wildly at the login screen and asking what to do.

Doing my best to be patient, assuming she wasn’t computer savvy, I explained that she needed to enter her university username and password on the login screen. It’s the same for everything—Wi-Fi, other services, etc. However, she was dissatisfied with its appearance.

I figured she was upset about the operating system's appearance. We'd recently upgraded to Windows 10, so perhaps she was just unfamiliar. I explained to her about the upgrade, but she just kept asking for "the university".

Despite her complaints, I managed to help her log in while she tutted and sighed. Once logged in, however, she became even more irritated. Noticing her fluent typing, I was confused about her seeming lack of digital skills. She began furiously clicking on random software, getting agitated when “university” did not magically appear.

She clicked on a random icon, opening a graphing software meant for physics students. She was furious about this and yelled at me, even though she was the one who clicked.

Mind you, my co-workers were spectating and chuckling while I attempted to assist her. She periodically yelled, “I WANT UNIVERSITY”, leaving me utterly perplexed. I guided her to open Google Chrome, which she thought was alien.

After eventually coaxing her into opening the default university homepage, she started working. To my chagrin, she was back ten minutes later, demanding a guest account. Oddly, she kept disregarding my female colleagues and addressing me directly.

When I informed her we didn’t provide guest accounts and that they would be redundant anyway, she expressed concern about others accessing her files. I then had to decode the concept of server-saved files, only to be met with resistance once again. She repeatedly asked for a guest account, and I consistently turned her down.

In an attempt to win her case, she displayed some cleavage and pleaded for a guest account. My response remained the same: No.

Just then, a senior staff member walked in. Post her confusing screed, he suggested using labs with windows 7 if she wasn't comfortable with Windows 10. Her response, "I WANT UNIVERSITY” sent me over the edge as I clarified that Windows was an operating system and “university” made no sense.

Fuming, she stomped out. I still haven’t deciphered her request, and I'm baffled how someone could simultaneously seem computer savvy, yet so lacking in basics. My best guess? Maybe she’s a Mac user?

Miserable JobsShutterstock

44. Some People Can’t Be Helped

Over my four years working in tech support, I've handled countless calls, but this one guy, well, he was something else. It was the most frustrating, yet retrospectively funny call I've ever taken.

One calm Saturday morning, he called in.

Me: "Good morning. How can I assist"?

Customer (C): "Hello. I woke up to my family complaining that there's no internet and the TV isn't working either".

Me: "Wow, that's certainly unfortunate. Let's see if we can identify and resolve the issue".

After he shared his home address, I ran a diagnostic scan. There was zero signal. We had to proceed with some basic troubleshooting.

Me: "Can you tell me where your modem is located, sir"?

C: "Next to my front door".

Me: "Great. Could you share which lights are on or blinking"?

C: "A few are on, but not as many as usual".

Me: "Is the 'online' light on"?

C: "No".

Me: "Ok, seems like no signal is being received. We'll have to determine if the modem or the incoming signal is the problem. Could you turn your modem off for about 30 seconds"?

C: "Umm, no"?

Me: "I beg your pardon"?

C: "That's YOUR job. I'm not touching the modem".

Whether he was serious or just joking, I was flabbergasted at how quickly the conversation had shifted.

Me: "Resetting the modem is the first step in troubleshooting and resolves nearly most of the issues—"

C: "I don't care! I'm not doing your job! Send someone".

Me: "We typically don't send our technicians to reset a modem. We ask customers to do it for us—"

C: "You will send someone, and you'll also have to answer for the service I haven't received"!

Me: "Without cooperations from your side, it will be difficult to assist you".

In the middle of this escalated tension, the customer threatened to complain about me and even showed up at our HQ. His threat made me chuckle because he lived 175 miles away and didn't have a clue what I looked like.

By the end of the call, I told him he was welcome to make a 6-hour round trip to our office instead of a thirty-second modem reset, and I promptly terminated the call. I reported the threat to my manager, who escalated the matter.

I wish I could say the story ended there. Unfortunately, the man managed to contact me again within minutes before I could divert his calls. During this call, he threatened legal action and demanded service cancellation.

I responded by informing him of the recorded threat warning and his service termination request, confirming a callback within two hours.

He didn't attempt to contact me again after that. I later found out he had indeed taken this matter to court, lost, and ended up having to pay for the rest of his contract.

Though his threat was certainly unpleasant, I never took it seriously. Recalling that day still makes me laugh, imagining him driving 3 hours, inquiring every woman's name at our HQ, and then returning home to an internet and TV-less household. What a foolish scenario.

Ridiculous 9-1-1 Calls factsShutterstock

45. Don’t Cut Out The Middleman

Let me tell you about an incident that happened in a German university around the start of the new millennium. The physics department was quite well equipped for the students. At the start of the academic year, the new students’ accounts were created by the student supervisors. I played the role of an intermediary between the supervision team and the real tech guys who kept things on track.

I ended up being the go-to person for support when the supervisors were stumped. One day, a student named Samantha Melina Butler was directed to me. Samantha was quite good with computers, but she was clueless about the problems she was having with her account. She could get into her account, but she had some trouble editing certain files. Interestingly, she found out that she had access to nearly all files in other people’s accounts, even including some professors' files.

I instructed her to activate her account and I opened a terminal. I examined her files and everything seemed completely normal. She shouldn't have had access to other people's files. That's when I noticed her username. She had requested her initials as her username: Samantha Melinda Butler: smb. When I investigated, I realized the student supervisor had made a major blunder.

Simply put, Samantha had obtained all the privileges of the "ServerMessageBlock" (smb) because of her username. Plus, every user was part of the group smb. Funnily enough, the supervisor who set up Samantha's account couldn't comprehend why this mistake was his responsibility.

Tech Support Horror StoriesPexels

46. User Loser

One of our clients relies on us for all their server and networking equipment needs while another company takes care of their helpdesk services. I was at their site troubleshooting a network issue when one of their employees, quite upset, insisted that I immediately rectify some problem with her workstation.

I told her gently that I wasn't able to help as we did not offer such support. Our conversation went something like this:

Me: I'm afraid I can't assist with individual tech issues.

Her: What did you just refer to me as?!

Me: (Confused) A... user?


Sadly, nothing could pacify her after that. She expressed her outrage claiming she'd been insulted and refused to listen to my explanation. I ultimately had to overlook her reaction and complete my task. The following day my boss approached me with a complaint he'd received regarding my conduct. Surprised by the accusation, given that I typically maintain a calm and professional demeanor, he asked me for an explanation.

Once I related the incident, my boss couldn't hold back his laughter and simply walked off.

Tech Support Horror StoriesShutterstock

47. Everything AND The Kitchen Sink

This just unfolded. A team leader in my area couldn't figure something out on Excel and reached out to me. I asked her to email me the spreadsheet, so I could examine it firsthand. Instead, she sent me a link... to the document on her own desktop.

I could see the headache looming because I knew her well—a straightforward explanation wouldn’t register. But I had to attempt anyway. I replied, highlighting that I can't open files on her individual computer and that she should send the file as an attachment. That's when things got ridiculous. 

She answered, "You can find it on the desktop. If the link doesn't work, just open it". I tried once more, emphasizing that her desktop and mine were two separate things, and I could no more access her files than she could mine. Then things got totally absurd. She reasoned that she’s accessed the recycle bin, I have one too. So logically, I should be able to get to her files.

At this juncture, I decided to drop formalities. If she's upset, my long-standing service can handle the backlash. I excused myself and put on the kitchen tap. Working from home, I knew she could hear it. I got back to my desk, and asked, “I've just turned on my tap. Is your sink filling up with water”?

The silence, lasting a good few moments, was golden. I could almost hear the gears working overtime in her mind. She finally caught on, expressing her understanding in a nonchalant tone, “Alright, that makes sense. I'll attach it and send it over”.

Tech Support Horror StoriesShutterstock

48. They Are Out To Get You

So, my day yesterday was out of the ordinary, to put it mildly. I had a scheduled meeting at noon, so my morning was fairly typical. At twelve, I went into the meeting room for a video review. The IT Manager, along with the Executive VP of IT and technology, were present. The meeting started humorously, with everyone struggling to get the HR Manager's video to work.

I guided her through the simple fix.

Me: Did you try unplugging it and reconnecting it?

HR Manager: Oh, silly me. I should have realized it was something like that.

No sooner did we begin the meeting than it became apparent that she was out to get me.

Her: I have 19 complaints lodged against you this year. Can you clarify these?

Me: Is that all?

Her: Uh, yes. Can you account for these?

Me: As you’re aware, every complaint has a different context, and most are unfounded.

Her: So, you’re suggesting these grievances were incorrectly lodged?

Me: Precisely.

I presented the same file she may have had.

Me: This person complained on Feb 12th that I declined his request.

We continued discussing the complaints like this for about half an hour. Only one of them had substance. That's when she brought up an instance where I had made a technical error and had to fix it a bit later. Then came the bombshell.

Her: Let’s discuss the fire incident.

Me: That I STARTED!?

My IT Manager and Vice President echoed my surprise in disbelief.

Her: Going by your report, a fire erupted inside the wall, caused by an overloaded fuse box when the third servers’ rack was plugged in, which destroyed much of the building.

Me: Your summary is correct, but you've omitted the part where the fuse box was hidden behind a cabinet. That's why the fire started.

The meeting finally reached a point where the Vice President had to intervene.

Vice President: Let's put a stop here. You, hold your respect towards senior members. However, HR Manager, he is correct. (To me) Do you wish to continue working here?

Me: Yes.

The Vice president instructed both the HR manager and me to apologize to each other. After this tense encounter, I went back to my desk and sent an apology to the HR Manager, receiving her apology in return by the end of the day.

Tech Support Horror StoriesShutterstock

49. You Don’t Know Jack

Two months into my stint as a small office's systems administrator, we hired Jack. He's an intern with a mom who's friends with the boss's wife. Coming from the wealthiest county in the state (just like my boss), Jack's always had a silver spoon in his mouth.

The moment we met, an air of entitlement clung to him like a week-old sweaty sock. "Jack, meet our...uh...tech...guy". My boss struggled to introduce me, typical for someone who rarely uses a computer.

Jack reached out to shake hands. "Oh, cool. Great to meet you".

I replied, "Glad to have you on board".

He was giddy to start, asking eagerly, "Do I get a business email"?

"It'll come eventually. For now, we have an intern group email. I'll get you the details soon". This is typical—interns usually share an email group at first.

"You run the firewall, right"?


"So you can block and unblock sites"?

"Sure thing". His enthusiasm was infectious.

"Great! Pleasure meeting you". Boss and Jack headed off for more introductions. Now you might wonder why I'd label Jack as the worst user ever. He seemed polite with a sunny disposition, and he knew a bit about what I do. That's pretty good for most users. But just wait, there's more to this story.

As soon as he was out of earshot, Jack began complaining. Apparently, he told the boss he should have his own email to look professional. He claimed that as someone with experience, he was more than a mere intern. Problem was, if Jack whined to his mother, she'd nag the boss's wife, and she'd nag the boss.

Within an hour, the boss had me setting up a personal email for Jack. Not a promising start for an IT Guy and his user.

On day two, I got an IT ticket from the interns' workspace. The office, filled with computers and printers, is where the interns do their mundane printing jobs. To pass the time, they often play music from Pandora or Spotify. The ticket read:

"Hey, we're having issues with Spotify. Not crucial, but help if you can! Thanks".

I like these guys, always polite. I found some free time later, went to fix the issue, Jack observed intently.

"We can use Spotify here"? He asked.

"Sure," I replied.

"And Pandora, too," added another intern. Problem resolved, I left the interns, including Jack, happier with the return of their music. But then, I discovered a note on my desk that made my blood boil. My boss already knew about the music-playing. However, he suddenly saw Spotify as a major security threat, perceiving it as a gateway for viruses, malware, and even cyberterrorists. He wasn't pleased with me for allegedly leaving our system vulnerable and demanded I fix it.

When I called him to find out who had given him this misinformation about Spotify, the answer was, predictably, Jack.

Trying to correct his misunderstanding, I explained that Spotify wasn't a threat, but Jack interrupted me. He was on speakerphone in the boss's office saying: "Dude, don't blame me if you didn't know about the security risks". Shocked by this audacity, I was speechless as my boss hung up, still insisting I fix the issue.

Tech Support Horror StoriesShutterstock

50. Not Your Usual Day At Work

I've been terribly distressed by this experience and I feel sharing it might give me some peace. I stay in Mexico where life isn't exactly a bed of roses. But I've learned to look out for myself and not make adversaries, though sometimes, fate has a way of sneaking up on you.

I'd just completed my training and received a certificate in computer repair. I got an early start at the local computer store. The day was ordinary until around 1 pm. This guy walks in, wants his hard drive totally cleared and a fresh installation of Windows 7.

I didn't probe much, just took the computer to the back room and started working on it. Spruced it up a bit, removed dust, and was about to boot it up when everything went haywire. The front door glass shatters, loud voices fill the room. I find myself face to face with this man screaming at my boss and his initial customer to get down. Before I can think, I'm thrown onto the ground.


Me: Nothing! I hadn't even started! Was I just cleaning it!

The Man: You're lying!!

Me: Look for yourself, it's just as it was brought in!!

I then heard another person take the PC away. It seemed like an eternity until they finally left. I pulled myself together and staggered to the front. My boss was on the phone, sobbing. I didn't register the sirens until then...and then realized the original customer was gone.

They didn't allow me to watch the security footage but I discovered the missing customer was a cartel member. His body was found hours later. Staying on that job was only because I was in dire need of the money. I never found out what was on that hard drive. But maybe I'm better off not knowing.

Tech Support Horror StoriesShutterstock


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