10 Amazing Tech Support Stories That Actually Happened

Joel Lee 18-12-2015

As technology keeps advancing, tech support becomes ever more important Which Big Company Has The Best Tech Support? MakeUseOf Finds Out There are few things in life that bother me more than bad customer service. Between suffering through automated menus, trying to communication with people whose accent is undecipherable, and voice recognition systems that make me... Read More . Unfortunately, between the people who work tech support and the end users who need tech support’s help, it’s hard to have much empathy for the other side.


Tech support might be nightmarish for you, but here are some absolutely amazing stories that give a glimpse into the lives of these unsung heroes. Tears, laughs, and even justice awaits in these Tales of Tech Support.

1. No Act of Kindness Is Too Small

Here’s the sad thing about IT help: support staffers think all end users are idiots while end users think all support staffers are incompetent. Both sides tend to forget that the other side is human, and that leads to a lot of misunderstandings.

Or in the case of this story, a lot of heartbreak and reflection. You just never know what someone else might be going through, and a small act of kindness could be the one thing that brings an immeasurable amount of joy into someone’s life.

Like I said, I’ve dealt with this before so I tried my best not to take it personally, but eventually I had to ask him if we could book a service tech to the home (a courtesy call) to get his TV working correctly. Unfortunately, our booking calendar was showing an appointment 3 days out. That’s when he dropped this on me:

“Don’t bother sending a goddamn technician, because I’ll be dead by then. I’m 94 and TV is the only thing I have left, are you really going to make me wait for a tech?”

Read the full story here and be prepared to be rendered speechless.

2. Paranoid and Rightfully So

Anyone who’s been in the IT business for more than a year has likely run into their fair share of conspiracy nutjobs and paranoid lunatics 4 Reasons Why IT People Ignore Your Requests for Help Asking the right questions can get you immediate help or feedback. But there is an art to the intelligent query. Here are four reasons that could be stopping you from asking better questions. Read More — but every once in a while, the conspiracy theories and paranoia end up being justified.


She insists her husband is monitoring her every move, tracking her vehicle, monitoring her computer, and recording her in her own home. Here’s where it gets interesting: She claims that she knows all of this, because he has told her about it.

In fact, he has gone so far as to threaten her life if she tries to tamper with any of it. She says she has tried to apply for a protective order against him, but ostensibly without some sort of evidence of his behavior, nobody would take her seriously.

I give her the crazy litmus test and I tell her that in order to gather evidence discreetly we would need two of our senior consultants to investigate. $300 an hour, four hour minimum.

She pulls out her wallet. F***, she’s serious.

Read the full story here. It reads like a thriller novel, but never edges into unbelievable territory. It’s a little long but definitely worth the read. Skip the techno-jargon in the middle to save yourself a bit of time.

3. The 5:45am “Friend of a Friend” Call

One of the worst aspects of being an IT professional is that family members, friends, and friends-of-friends assume you’re always willing to give free advice. It’s even worse when they expect you to help, and worst yet when they demand it of you. How would you like to be called at 5:45am by a stranger?

Me: “Hello?”

Stranger: “Hi DallasITGuy, this is $GuyYouBarelyKnow. Do you have a second? I can’t get my laptop on my home wireless and I really need to check to make sure my flight is on time.”

Me: “Who the f*** is this again?”

Stranger: “This is $GuyYouBarelyKnow. I’m a friend of $OtherGuy. We met at $NeighborhoodBar a couple of weeks ago. My Internet’s down and I remembered you’re in IT so I looked up your number and gave you a ring. Can you help me real quick?”

Read the full story here, but if you’re prone to blood pressure spikes, you should probably do yourself a favor and move on to the next story.

4. Mom’s Broken Internet

Sometimes tech support requests are about more than just tech support. That’s what this IT worker discovered when his mother contacted him 5 Tricks To Get Your IT Department To Help You Faster How many I.T. techs does it take to change a lightbulb? None, you didn't submit a help desk ticket for it. Read More about her broken Internet connection, and it took him a bit to realize what she really wanted.


My phone rang last week while I was home. Day off.

Mom: “Do you have a minute honey? My internet doesn’t work, either computer, nor the tablet either.. I was thinking maybe you could come have dinner later and look at it? I bought chicken, soft cheese, wine, and I’m baking a..”

Somewhere later down the menu I already fixed it. I work at the telco, and have access to my tools remotely, I saw it had no valid IP so I reset the modem and the router we provide her. Basic lease renewal issue. It happens, everything else is green.

Me: “Boom, magic, you’re online mom.”

Mom: “Whaa? … Oh. You’re right.” Sounds disappointed. “Thank you, that was really fast, I guess I won’t trouble you to come over then.”

Read the full story here, but more importantly, remember that there are people in your life who wish you had more time to spend with them!

5. Accidentally Got the Secretary Fired

Humans are being replaced by robots Why Replacing Humans With These Robots Makes Sense Are there any jobs where automation and precision are so valuable that robots are actually more deserving of them than humans? Read More at an alarming rate, and many more jobs will soon be at risk 8 Skilled Jobs That May Soon Be Replaced By Robots Are machines coming for your job? You might be surprised. Recent advances in AI are putting white collar jobs at risk. Read More . This IT support story is a hilarious account of how one man’s generosity came back and bit his coworker right in the rear.

Of course, being the bright-eyed, not-yet-disillusioned, early-twenties computer nerd eager to prove my worth, I didn’t just want to do my job. I wanted to do it great and really impress people. Go above and beyond and be appreciated.

And the complaining secretary from that morning had plopped a great opportunity to show that I’m a real go-getter right into my lap.

Read the full story here, and while you’re at it, you might want to take a moment to consider what will happen when robots take over all of our jobs What Happens When Robots Can Do All the Jobs? Robots are getting smarter fast -- what happens when they can do every job better and cheaper than human beings? Read More .

6. “I Think We’re Being Hacked!”

The funniest — and most frustrating — clients in tech support are those who have so little computer experience that everything frightens them and they have no idea how to deal with even the most mundane of problems.


The phone rings.

Her: “Yes hello. This the secretary of the CEO. We need you to come over NOW! We have a big problem.”

Me: “What seems to be wrong?”

Her: “Mr. CEO is trying to open a file in Word, but every time he does this, scrambled text is showing up. I THINK WE ARE BEING HACKED!”

Read the full story here. Hopefully stories like this help you to better sympathize with IT workers. They have to deal with a lot of crazy and inane support requests 5 Things Users Tell IT Support and What They Really Mean Sometimes what people tell you they need, isn’t always what they really need. Sometimes, you just have to know better. Read More on a daily basis, so when they’re short with you, don’t take it personally.

By the way, Hollywood’s depiction of hacking is never what it really looks like. Most of the time, hacks are entirely invisible. Instead, you should worry more about installing a good security suite The 5 Best Free Internet Security Software for Windows Need antivirus, anti-malware, and real-time security? Here are the best free internet security software for Windows. Read More and adhering to these most effective tips from security experts 8 Tips for Online Safety Used by Security Experts Want to stay safe online? Then forget everything you think you know about passwords, antivirus and online security because it's time to be retrained. Here's what the experts actually do. Read More .

7. Google’s Phenomenal Customer Service

Whether you love ’em or hate ’em, you have to give Google props for what they did for this person who needed help — with a product that wasn’t related to Google in any way whatsoever.

My friend bought a Netflix box for a TV, and when it wouldn’t work, asked me to come set it up. I couldn’t get there until after work, and when I did, it was working. She said she called Google to fix it…

Read the full story here. To be fair, the Google support worker probably used Google to help her troubleshoot her setup, but still, it’s nice to know that these kinds of quiet moments are happening out there even if we don’t always hear about them.


8. IE vs. Chrome, What’s the Difference?

Tech-savvy people tend to forget just how much jargon, knowledge, and experience is necessary to become comfortable with technology. Things that are simple to you and me might be impossible to grasp for the average user — such as the difference between Internet Explorer and Chrome.

Me: “Ma’am, it looks like everything works well here, Internet is working alright, you sure it’s not a problem with your connection?”

Woman looked at me like I offended her ancestors


Oh. I got it… Someone deleted Internet Explorer from her laptop, changing it with Chrome. Poor woman didn’t have a clue what Chrome is.

Read the full story here and try not to facepalm too hard or judge the woman as a stupid human being. We’ve all been there at one point or another, and that’s why sites like this exist: to help people learn!

9. Voicemails from His Daughter

IT support folks are rarely thanked when they do a job well done, but more so than that, they’re even more rarely recognized when they do hero-level work. Consider this story of an innocent help desk worker who does his best to help retrieve a man’s important voicemail files.

I don’t remember his name but his problem description was just “needs to remove audio file from phone”. Figured heh this should be easy (a typical old faculty member needing help with his phone kinda thing), I asked him to come sit at my station and took a look at his problem.

He unlocks his phone for me and I navigate to his phone app and pull up the voicemail. While I was looking at the phone he said there were 3 voicemails from the previous weekend were the ones he wanted saved. I played the first one on speaker to see if they were playing properly.

“Hey dad…”

Read the full story here. If there’s one thing to take away from this story, it’s that even the simplest or humblest of tasks — like saving voicemail files — can make a huge impact on someone’s life. Never underestimate how you might be helping others.

10. The Case of the 500-Mile Email

This last IT support story is equal parts fascinating and hilarious. What do you do when someone tells you that they can’t send emails to recipients who are more than 500 miles away? The solution to this “impossible” problem will definitely catch you off guard.

I was working in a job running the campus email system some years ago when I got a call from the chairman of the statistics department.

“We’re having a problem sending email out of the department.”

“What’s the problem?” I asked.

“We can’t send mail more than 500 miles,” the chairman explained.

I choked on my latte. “Come again?”

“We can’t send mail farther than 500 miles from here,” he repeated. “A little bit more, actually. Call it 520 miles. But no farther.”

Read the full story here. If anything, this just goes to show that IT workers occasionally have to deal with some really weird issues and come up with brilliant diagnoses.

IT Workers Deserve Our Appreciation

Tech Support

The next time you think that all IT support workers are lazy and incompetent, we urge you to remember these stories. Consider what they have to deal with on a day-to-day basis, and remember that some IT workers truly are modern-day heroes.

On the other hand, be aware that there are predatory people out there who disguise themselves as IT support folk What's Fake Tech Support & Why You Shouldn't Trust Everything You See on Google You’re sitting at home, minding your own business. Suddenly, the phone rings. You pick up, and it’s Microsoft (or Norton, or Dell, or …). Specifically, it’s a support engineer, and he’s concerned – concerned for... Read More in order to scam and deceive innocent users like you and me. Learn to identify these tech support scams Anatomy of a Scam: The "Windows Tech Support" Con Examined They're constantly on the prowl: cold calling scammers claiming to be from "Windows Tech Support". We were targeted by one of these con artists and here's what happened. Read More so you don’t become another victim.

Have any IT support stories of your own? Whether you were the helper or the end user, we want to hear them all! If you have no stories, then tell us about your biggest IT pet peeves!

Image Credit: Tired female customer service by Tyler Olson via Shutterstock, Cartoonresource via Shutterstock

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  1. Anonymous
    December 29, 2015 at 1:23 am

    My biggest concern with tech support is that so much of it is now outsourced, and I end up with someone in India who can barely speak English.

    It's a nightmare!

  2. Anthony
    December 28, 2015 at 5:45 pm

    The true test of your career choice in IT is how you see your customers. If you see your customers as fools and helping them is an irritation or beneath you, then maybe you have chosen the wrong career field.

    If on the other hand, you see your customers as specialists in their own field and you see computers as the half baked, poorly engineered systems that they are (not nearly as reliable as the most unreliable automobile), then you develop an appreciation for the disconnect between the need for a pencil and a desk vs the use of a word processor and Windows.

    If computers were reliable and as secure as a pencil, there would be no need for IT. Be happy that computers are buggy and force users to work in patterns that are unnatural. If Windows and Mac OS X were as appliance-like as an iPad or iPhone, 90% of IT would be out of a job.

    And before you say that IT would be developing software, realize that IT pushes the buttons that software engineering creates. Unix scripts run through an interpreter that some software engineer (or programmer) created to run them. Unix scripts execute programs like "grep" and "ls" that again software engineers (more likely programmers) created. There is a considerable difference between using a shell script language & command line interface programs like grep (IT) vs developing commercial software like MS Word (software engineering).

    Software development ? Information Technology.

    So thank the programmers for creating buggy unintuitive programs that crash, confuse and dismay. This is why the users come to you. And coming to you after being enormously frustrated and under pressure to get their real work done is no small matter.

    I love my users. Some are creative professionals, some are physicians, some are mechanics, all of them need help and all of them are an opportunity for me to help someone have a better day.

    I'm a software engineer and I do IT as a sideline because I want to see what the users of my software go through so I can engineer better solutions which require less if not zero IT intervention. My objective is to make IT as prevalent as pencil/paper support people.

  3. John 'Meme' Cena
    December 19, 2015 at 5:41 pm

    It appears another internet user is able to go to /r/talesfromtechsupport and sort by top. Normally I would disapprove, but since you provided links to the original good on you for not being buzzfeed.

    • Joel Lee
      December 23, 2015 at 9:47 pm

      Credit given where credit is due!

  4. Anonymous
    December 18, 2015 at 1:53 pm

    "support staffers think all end users are idiots "
    During my more than 10 years in support, that opinion has been reaffirmed time and time again by empirical evidence. It seems that most users are confused by technology more sophisticated than a sharpened stick.

    "end users think all support staffers are incompetent"
    I know about computers. I know how to spell "Windows". If you can't fix my computer to run the way I think it should run, you are incompetent! /sarcasm

    • Joel Lee
      December 23, 2015 at 9:46 pm

      Haha, it's funny (in a sad sort of way) how big the divide is between users and support staffers. The enmity goes both ways and it's hard to see a way to remedy that.