Tech's lighter side: America's funniest IT blunders

IT pros share behind-the-scene stories of the job, from personal bloopers to bureaucratic nonsense

Diane Macdonald

Behind the scenes with tech pros

Every week in the InfoWorld Off the Record blog, IT pros take us behind the scenes of their jobs. The anonymous stories feature ways of dealing with personal bloopers, unforgettable help desk calls, fights against bureaucratic nonsense, and everything in between. We present some of the challenges the tech pros shared with us, and we thank the writers for giving us a glimpse into the ups and downs of their IT careers.

IT pros, if you have an on-the-job experience to submit, send your story to We'll send you a $50 American Express gift cheque if we publish it.

Kutay Tanir

The puzzling problem

There are times when troubleshooting goes as planned. And then there are those puzzling problems that won't go away, forcing IT staff to stubbornly examine every detail yet again and go back to the basics.

For example, a user brings in a laptop with a failed fan, random pop-ups, and BSODs, then has similar issues with the replacement. The techs try one thing after another, finally discovering the cause of the problem: A furry friend who thought the laptop was the perfect spot for a nightly nap.

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Hindsight is 20/20

Everyone makes mistakes, but it's certainly no fun to do so -- especially in that heart-stopping space of time spent wondering what the repercussions will be.

For example, a networking newbie chooses the wrong RAID array option when working on a SQL server problem -- then spends a tense all-nighter fixing the mess. And still has to face the boss the next morning.

To err is human, but it can be enlightening once you're back on the right track.

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Vitaly Korovin

Follow the clues

There can be more to a tech problem than meets the eye. Even though an IT job may not be in a law enforcement department, criminals are everywhere, and a routine tech task can turn into a chase.

In one story, an irate customer blames the accounting system for missing inventory. But the wily tech senses foul play, sets up a sting, and proves the technology's not to blame. Let's face it: Many criminals are no match for an observant tech.

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User (un)awareness

Most end-users aren't expected to master high levels of technology. But there are those folk who don't seem to grasp common sense or basic etiquette. Even a little more awareness would make their lives easier -- not to mention the lives of the techs who have to help them.

Take the unfortunate admin who was handed a smartphone that didn't work. Way too late, the user 'fesses up that he'd dropped it in the urinal. Add to the tech toolbox: Rubber gloves, hand sanitizer, and patience, all in large supply.

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Sometimes enough is enough

Patience and politeness are expected from IT staff. But the same can be said for any employee -- it's called good manners. A person can put up with only so much rudeness and timesucks.

For instance, what can a techie do about pushy vendors who just don't quit? One IT pro came up with some techniques, such as transferring the vendor to the fax line or asking them for their credit card number, so they could be billed for the conversation. IT staff put up with a heckuva lot and sometimes have to push back to keep sane.

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Jutta Kuss

The bureaucratic enemy from within

Just think what could be accomplished without red tape or unrealistic company policies! OK, that was fun. Now back to real life.

Take, for example, an IT pro who needs to move a fax machine. It should be a quick operation, right? Not when a micromanaging CFO is involved, dragging out the project for more than a month.

Sometimes the situations resolve themselves, and other times they don't. But get enough of them and it may be time to find another job.

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Daniel Deitschel

Beware the unknown

Sometimes, IT must reckon with an unfamiliar force. The first step is to get through the situation. Then evaluate what to do next. One IT pro faces a bad scenario after a takeover when a "seasoned" manager from the new company oversees the systems migration. The project's fraught with poor planning, communication, and execution, yet the manager deems it a "success." Seriously?

At times like this it can be hard to see the forest through the trees. So take courage, and proceed one step at a time.

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Igor Stevanovic

Surprise! Actions have consequences

We've all had to put up with unsavory characters at the office or witnessed questionable antics that blur the line between what's acceptable and what's not. It's maddening when these characters get away with it.

But at times, consequences fit the action, as one IT pro discovers after putting up with a certain coworker for years. The arrogant techie lands the job of senior network admin, but the jig is up when he installs rogue wireless routers that cause problems for the top execs, and his history of incompetence catches up with him. Employee X, meet cause-effect. It's high time you got acquainted.

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Monalyn Gracia

Sleazy boss, meet justice

And sometimes, it is the mighty exec that falls -- such as one project manager who tries to procure IT equipment through lying, flattery, threats, and eventually theft. It's only appropriate that IT takes him down. Good riddance!

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Gunnar Pippel

Get out, get out while you can

Some workplace situations are simply unbearable, and escape is the only option. In one story, an IT pro is thrilled to land a great job during the recession, but discovers that the boss is ineffective, makes unreasonable demands, and even offers unsolicited parenting advice -- at a company that ignores personnel problems and sees a high turnover rate. Looking back, the techie is proud to have stuck it out for three whole months before leaving.

Well, at least such experiences show how bad things can get.

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The penny-pinchers

Upgrade cycles are a given in tech. However, convincing the accountants to loosen the purse strings for those upgrades is not. Why spend money if it still works? For example, an IT contractor responds to a network problem and discovers how bad the site's cost-cutting measures are: No on-premise IT staff and a server room so sloppy that the source of the problem takes days to find.

Maintaining old tech is always an adventure, but at least it's not another average day at the office.

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Beau Lark

Hold on to the positive

Studies show it's human nature to dwell on the negative. But once in a while, seemingly stressful situations end up as just the opposite, bringing unexpected accolades -- even apologies.

Case in point: An important customer calls about a major problem with a new server. A tech draws the short straw, finds that the problem is simple to fix, and is lauded a hero all because the on-site IT staff failed to read the manual. It's all in a day's work, but such instances are worth remembering.

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Plush Studios

Job stress got you down?

If you need more diversions, chuckles, or aha moments, Off the Record archives are full of tales from the IT trenches. Such as the best Off the Record stories from 2007, 2008, 2009, 2010, and 2011.

And write up your own crazy-but-true tale about managing IT, developing apps, or supporting users and send it to If we publish your story -- anonymously, of course -- you'll receive a $50 American Express gift cheque.