9 Real Tales of Tech Support Gone Wrong—And How to Save Yourself

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Tech support gets a bad rap for being a boring job for boring nerds. But if you’ve worked in IT, you know that your job is anything but monotonous.

To prove just how out-of-the-ordinary a career in IT can be, I got in touch with nine IT professionals who’ve done their time in the support trenches. I asked them to share their weirdest, wackiest, and downright oddest tales of tech support gone wrong.

And since every experience is a learning experience, I’ve tried to add a lesson at the end of each anecdote so we can all keep our faith in human progress intact.

1. Some clients don’t understand the basics

“Before I started my entrepreneurial journey, I was an outside sales technician for a Fortune 50 company. I was a level-three technician, so I would only be sent out to our ‘white glove’ customers in the event of a catastrophic event. I had 24-hour direct access to our smartest engineers if there was something I was not able to troubleshoot.

“I got dispatched to one of the largest universities that had requested someone come onsite immediately because one of their exchange servers was down. I drove two hours to access the situation…on a Sunday.

“I knew the IT director because I had been out there before, but needless to say, this was a wasted trip.

“After entering their server room, I ran my diagnostics and found there wasn’t any power going to the mainframe. Come to find out, the UPS (uninterrupted power supply) had been disconnected. I didn’t have the heart to tell him, so I told him that the power supply was bad and I’d just fixed in. Literally, it could have been back up and running in seconds.”

 KEY TAKEAWAY:  While it’s easy to mock those with—shall we say—less advanced technical skills, keep in mind that condescension is easy, but kindness is always the better choice. This is especially true when dealing with high profile clients and customers. People make mistakes all the time, including really, really stupid and simple mistakes, like forgetting to check if something is plugged in.

Treat everyone like a genius, even if that means withholding certain facts, and I guarantee your customers will give you endless great reviews.

2. Saying ‘no’ is okay; it’s also the right thing to do

“My company sells workplace engagement software that allows employees to share feedback, both publicly and anonymously, with their team. The most illogical IT request encountered in my last decade of building software was from a client who worked in HR tech for a Fortune 25 corporation.

“During a virtual demo in front of my sales engineering team, the client demanded backdoor access to unmask the identities of all employees who posted anonymously, so he and other senior management could see who exactly was posting feedback. Aghast and in dead silence, my team looked at me in shock. We couldn’t believe how unethical this guy was—like it was normal to lie to your employees and tell them their feedback was anonymous when in fact the opposite was true.

“Needless to say, that deal was dead on arrival. My team said, ‘Absolutely no,’ to that request and never heard from him again. Walking away from half a million dollars never felt so right.”

 KEY TAKEAWAY:  If you compromise your company or your product, it will come back to bite you. The customer is not always right, and in fact, sometimes they can be very, very wrong. Although it might hurt to walk away from a lot of money or a prestigious client, you must always think about how your decisions will affect your company long-term and do what you know is right.

3. The customer is always…weird

“I had a case where I was recovering someone’s iPhoto library, and it was showing each photo for a solid 1.5 seconds as it imported. The guy and I were discussing something while watching his photos import. We got to a natural conversation break and were staring silently at his screen when a picture of his topless wife popped up. Very awkward 1.5 seconds. We continued talking afterward like nothing happened.”

 KEY TAKEAWAY:  Working with customers means you’re never going to stop being surprised by just how weird people can be. Whenever you find yourself in a really strange situation, do your best to handle it professionally. However, if a customer or client makes you feel uncomfortable or repeatedly comes in with “icky” requests, remember that you’re allowed to speak up or say something to your manager or HR department.

4. A lesson in following your instincts

“One of the weirdest requests that we have ever received was for network wireless penetration.

“Now, we actually do wireless penetration, pen testing, and remediation, but this one was for a client who claimed that his branch office router had failed. But we couldn’t get in there to reset it, because they are in a sensitive industry. It was a little confusing at first, because we’re actually certified and qualified to work on many sensitive platforms, so it brought up a red flag.

“Basically, we sat outside with a Raspberry Pi Kali Linux and, using wireless capture, we were able to grab about six hours worth of Wi-Fi traffic. Utilizing our AWS instance, we were able to spend about $30 and crack the password.

“But there was something nagging the back of our minds, so I began to investigate what was actually in that office. Come to find out it was one of the client’s competitors.

“On learning that, we instantly told the client that we were unable to crack the password and we could not help them without actually being on the network.

“We actually reached out to the competitor and admitted what we were doing and apologized. The competitor was impressed and actually hired us.

“The original client was acquired by a regional group who no longer need our services, and the competitor is still with us to this day.”

 KEY TAKEAWAY:  Although it’s a cliche, honesty is usually the best policy. While Harmon and his team could easily have said nothing, and the company whose network they penetrated would have been none the wiser, being forthright about what they’d done helped them gain a client.

Not only did his team demonstrate its technical prowess, but it showed their new client that they were trustworthy and, therefore, good partners in business.

5. That wasn’t in the job description…

“Weird request #1: Our CEO called my senior analyst one morning and asked if he could try to fix his heart rate monitor watch. He said that he was working out, and somehow his grandson had dropped it in the pool. My analyst looked at me with a face that said, ‘What the heck am I supposed to say?’ I tried to help the CEO myself. We ended up being able to quickly fix the watch, but it was a very funny situation overall.

“Weird request #2: I received a direct IT ticket, followed by a face-to-face enquiry right after, asking me to try to fix the air conditioning building engine on a very warm summer day. I did my best to contact the building manager and make him bring the right people.

“Weird request #3: I received a request to try to fix the coffee machine. The argument written on the ticket was that ‘…it has a power button on it, therefore it is IT scope, once we do not have no one else with basic electronic skills around…’ [sic].

“In all those situations, there is a genuine pain point for our customers, and they really need help. So our first action was to try to find the correct and skilled personnel to do those tasks. And if we didn’t find them, then we tried to do our best to solve the issues.

“In IT services as a whole we have to be patient, always try to put ourselves in our clients shoes, and do the best we can to make our customers happy.”

 KEY TAKEAWAY:  At Capterra, one of our core values is being ridiculously helpful. That often means going above and beyond our job descriptions so that our customers have a good experience and, ultimately, become repeat customers.

If you’ve got a million high priority projects going on, you should probably redirect weird requests to the correct personnel. But if you’ve got the time to try to help someone to the best of your abilities, why not go ahead and do it?

6. The customer is always right, except when they’re not

“My ‘favorite’ customers were the ones who didn’t understand the meaning of the word ‘warranty’ and what that entailed. I had a customer come in with an iPhone that had a shattered screen. It was an iPhone 4, which is outdated and not really worth repairing, considering the value of the device. The customer let me know she had dropped her phone, shattering the screen, and had been unable to power it on ever since.

“I told her we could fix the display but couldn’t guarantee it would solve the problem of the device not powering on. After a few minutes of thinking about it, the customer asked me if her warranty would cover a new phone. I explained that our warranties don’t extend beyond two years, and that her phone was over 5 years old. The warranty also doesn’t cover accidental damage—only internal failures due to manufacturing issues.

“The customer didn’t understand, and started lecturing me about how much money she spends on Apple products … and that because of this customer loyalty, she ought to get a new phone.

“After I explained our policy a few more times, the customer demanded to see my manager, who told her the same. After declaring that this is the reason why Millennials aren’t respected, the customer left and came back a few weeks later and tried the same thing with another tech specialist. I almost have to commend the persistence.”

 KEY TAKEAWAY:  While you should always try to help a customer or client to the best of your abilities, sometimes there’s just nothing you can do for them. If you’ve been polite and helpful while a customer has been manipulative and rude, you can claim the moral high ground here. I give you permission to (politely) tell them to take a hike. (Disclaimer: Your manager might not approve of that exact phrasing.)

7. Don’t forget your morals

“Our service helps users calculate loan installments online from several banks at the same time throughout all of Latin America.

“It was based on this service that we received the strangest request when a client asked us to configure his campaign in our platform with incorrect formulas.

“If we used these formulas, they would mislead users to choose a loan that was not convenient.

“I believe that many more times than people imagine, the area of IT not only has to resolve technical issues, but also ethical issues on which its operation or algorithm is based.

“Luckily, the decision we made in the IT department was backed by the company, and everything ended up being successful, even though we lost the customer and the sale.”

 KEY TAKEAWAY:  Much like the situation Aventr faced in Tale No. 2, Rennella’s story serves as a good lesson in sticking to your guns. If you advertise that your product does one thing, but on the back end it manipulates variables or data in a misleading way, you’ll lose your customers’ trust forever, even if you gained a one-time client.

And given how fast word travels via social media and rating sites such as Yelp—or even Capterra—your reputation could be ruined overnight.

8. All hell can break loose, even in a church

“Sometime around 1997, an acquaintance asked me to set up a new server at her church. It was a three-week character building experience. The server had hardware problems, Windows NT 4.0 Service Pack 2 was unstable, the network wiring was the worst I’ve ever seen, and some of their desktop PCs really did go up in smoke. Two of their aging 486 PCs needed memory upgrades.

“I installed the memory sticks, turned the systems on, and smoke poured out of them a few seconds later. I quickly turned them off before the fires were out of control. I’ve never seen a computer behave that way before or since.

“I remember the office manager asking me if I had a problem with her building wiring. I said no, we’d figure out a way to make it work. I’ll never make that mistake again.

“This was supposed to be an easy job, but after days and nights struggling—and failing—to get this server up and running and PCs around the building connected to it, I’d finally had enough and bought 1,000 feet of CAT 5 cabling and ran it across the floors throughout the building myself. This made the office manager hate my guts even more than she did before because I ran ugly wiring along the floor all over her building, but I learned the hard way—Ethernet doesn’t work over vintage telephone cabling.

“I eventually got it all working but left with only a shred of my pride intact.”

 KEY TAKEAWAY:  Own up to your mistakes, and know when to ask for help. Doing both those things can save both you and your client time, money, and lots of frustration.

9. Guns don’t shoot computers, people shoot computers

“I had a client come in with a netbook who said he needed data recovery performed. I asked to see the device and, after looking it over, promptly denied service.

“The device had three holes in it, which the client informed me he had put in it with his handgun.

“When I inquired as to why he would destroy such a nice piece of equipment, he told me he found ‘nudies’ of his adult daughter on there. It was her netbook.

“He claimed in a fit of rage, he decided that was the best way to punish her for ‘such atrocious sins.’ Apparently, he had forgotten that all the family photos were also stored on that device.

“After much prodding from him, I removed the HDD from the back. Two of the rounds had passed through it, annihilating the platters and control board.

“He didn’t believe me when I said even the FBI couldn’t recover the pictures. We got a negative review on Google the following morning.”

 KEY TAKEAWAY:  OK…I don’t know what the lesson is from this story. Don’t shoot at your computer? The FBI doesn’t have all the answers? You will see strange things throughout the course of your career that you almost don’t believe are true? Your guess is as good as mine here, friends.

Tech support is anything but boring

If you’re not convinced that you have the most insane job in the world by now, then you should probably go back and read these stories again.

If you have stories of your own to share, leave them in the comments below. I’d love to hear them!

And make sure to share this post with your friends and colleagues who think your job only consists of telling people to turn their computers on and then off again.

Finally, if you want more tips and tricks on navigating the weird and wonderful world of IT, you can subscribe to our blog by entering your email here.

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About the Author


Kelsie Anderson

Kelsie is a former Capterra analyst.



Can relate to #5. People “assume” just because we have tech expertise that we can fix anything that is electronic related. I had people ask us if we fixed their home theater system, go to find out power supply was faulty to amplifier and some soldering later, back-up and running.

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