When Kevin Met Windows: The Hilarious Tale of a POS System Meltdown
If you’ve ever worked in an office, you’ve probably met a “Kevin”—that well-meaning but technologically challenged coworker who manages to turn the simplest digital task into an unsolvable mystery. But few Kevins can claim to have single-handedly brought a company’s entire Point of Sale (POS) system to its knees, all in the name of multitasking. Today, we dive into the unforgettable saga of “Kevin vs. The IT Department”—a true story from Reddit that’s equal parts hilarious and horrifying for anyone who’s ever worked in tech support.
Meet Kevin: The Accidental Nemesis of IT
Let’s set the scene: Kevin, a loyal employee with more than three decades on the job, has seen the company evolve from filing cabinets to floppy disks to, finally, a modern computer system where you can gasp use a mouse to click on things. While many of us take for granted the ability to navigate tabs and windows, for Kevin, every new feature is a potential pitfall.
When the company upgraded its sales software to a new, mouse-friendly POS system, Kevin’s approach was…unique. Instead of reusing the same window to make multiple sales, Kevin dutifully opened a brand-new window for every single transaction. And in true Kevin fashion, he never closed any of them. Nor did he ever shut down his computer.
Fast forward a few months: IT is scratching their heads because the entire sales system has slowed to a crawl. Reports that once took seconds now require a coffee break. The culprit? Kevin’s computer, valiantly chugging along with over 1,200 open windows—each one a silent testament to a sale made, and a mouse click misunderstood.
When One Man’s Clicks Become a Company-Wide Crisis
The situation crescendoed when Kevin, emboldened by his perceived mastery of the new system, decided to change a price in the POS. Instead of a simple update, the entire system crashed—hard. Corporate IT swooped in, suspecting hackers. But after some digital detective work, the truth was stranger than fiction: it wasn’t cybercriminals, just Kevin, crashing the system three times in a single hour with his earnest but disastrous attempts at data entry.
You might imagine IT would rally around Kevin, gently guiding him through the mysteries of window management. You would be wrong. After months of digital carnage, Kevin had become the department’s Voldemort—his name spoken only in groans. Recognizing the futility, his colleagues stopped offering tech support, leaving Kevin to his own devices (and disasters).
Desk Slams and Speakerphone Sagas
Undeterred, Kevin developed a new strategy: announcing his computer woes to the room, hoping someone would take pity and help. One day, he slammed his desk a little too hard and—miracle of miracles—his computer shut down. This, to Kevin, was cause and effect worthy of investigation.
Egged on by his coworkers, Kevin called IT (on speakerphone, of course) to report this supernatural shutdown. The conversation went something like this:
“Hi IT? This is Kevin!”
[audible groan from IT]
“My desk made my computer shut off. What should I do?”
IT, utterly defeated, assured Kevin to call back if it happened again—a promise he enthusiastically kept, reliving the saga every few weeks. Eventually, his colleagues convinced him that IT was pranking him as payback for his earlier POS crash, a theory he accepted with the earnestness only a Kevin could muster.
Lessons from the Land of Kevin
While it’s easy to laugh at Kevin’s misadventures, his story is a cautionary tale for every workplace:
- Never underestimate the power of user error. Even the best-designed software can’t outsmart determined confusion.
- Training matters. A little time teaching the basics can save hundreds of hours (and IT’s sanity) down the line.
- Patience is a virtue—especially in IT. If you’ve ever groaned at a help desk call, remember: today’s Kevin could be tomorrow’s cautionary tale.
Share Your “Kevin” Stories!
Do you have a Kevin at your office? Or have you survived similar tech blunders? Share your funniest workplace tech mishaps in the comments below—after all, laughter is the best debug tool. And if you’re in IT, may your windows always close cleanly, and your help desk phone ring a little less often.
Special thanks to Redditor u/seppukucoconuts for sharing this gem. For the original tale and more “Kevin” shenanigans, check out the original post on Reddit.
Original Reddit Post: Kevin pisses off the IT department