Skip to content

2025

When Desktop Icons Live in Monitors and NumLock is Witchcraft: Hilarious Tech Support Tales

Anime illustration of a confused user with desktop icons missing from a computer display.
In this engaging anime scene, we see the perplexity of a user facing the mystery of missing desktop icons. A relatable moment for anyone who's ever struggled with technology!

If you’ve ever worked in IT support, you know that sometimes, the only thing keeping you from rolling on the floor laughing is professional courtesy (and maybe the fear of being fired). From the legendary “cup holder” CD tray saga to asking if “the internet will fit on this USB drive,” tech support pros have seen it all. But every so often, a gem comes along that deserves a place in the Hall of Fame.

Today’s tales come courtesy of Reddit user u/dandy_g, who shared a pair of classic stories from their time as the all-in-one tech wizard at a small printing company. Prepare to giggle, groan, and maybe give your own monitor a reassuring pat.

How a Floppy Disk Boot Fiasco Taught One Company the Value of Hard Drives

Vintage PCs booting from floppy disks, showcasing Windows 95 and network connections in a retro office setting.
Dive into the nostalgic world of the 90s as we explore how our AS/400 programming firm utilized vintage PCs, network cards, and Windows 95 to connect seamlessly over Ethernet. This cinematic illustration captures the essence of our tech journey, highlighting the unique blend of custom software and file server networks that defined our daily operations.

Picture this: It’s the mid-90s, pastel colors and dial-up tones fill the air, and your boss just spent hundreds of dollars—per computer—to ensure that not a single byte of precious project data gets stranded on someone’s C: drive. How, you ask? By custom-ordering brand-new Compaq PCs with no hard drives, forcing everyone to boot from floppy disks like digital pioneers crossing the Oregon Trail. What could possibly go wrong?

Welcome to the world of AS/400 wizards, Netware magic, and the most creative (if ultimately regrettable) attempt at centralized computing you’ll ever hear. Today, we’re diving into a real-life tale from Reddit’s r/TalesFromTechSupport—one that’s equal parts nostalgia, facepalm, and pure IT comedy gold. Grab your 3.5" disks and let’s boot up this story.

The Case of the Missing Terminator: 1980s Tech Support and the “Ether” Panic

Cartoon depiction of thin Ethernet cables connecting vintage Mac SE computers in a school setting.
This vibrant cartoon-3D illustration captures the nostalgic essence of thin Ethernet networks connecting Mac SE computers in a school district office during the late '80s.

If you think IT support is wild today, imagine being a tech wrangler in the late ‘80s—armed with a trunk full of cables, a Radio Shack loyalty card, and nerves of steel. Today’s story, plucked from the nostalgia-fueled halls of r/TalesFromTechSupport, proves that some tech headaches are truly timeless.

Let’s set the scene: It’s 1988. The Mac SE is Apple’s hot new thing, shoulder pads are big, and Thin Ethernet (10BASE2 to the cool kids) is the backbone of school district networks—literally. Our protagonist, u/jasondbk, embarks on a 4-hour odyssey to save a small office from the brink of network oblivion. Why? Because one tiny piece of hardware—about the size of a large grape—keeps going missing. And the reason? Pure, unfiltered user logic.

The Elevator That Starts on the First Floor: A Front Desk Fable About Reading the Fine Print

Cartoon-3D image of a frustrated hotel receptionist amidst a busy front desk scene illustrating miscommunication.
In this vibrant cartoon-3D illustration, our hotel receptionist navigates the challenges of miscommunication in a bustling lobby. Dive into the post to discover the amusing yet relatable moments that come with working in customer service!

Picture this: You’re fresh out of college, working at a charming, fully renovated old hotel perched on your town’s bustling main shopping street. The building oozes history, boasts modern perks, and you—even as the friendly face behind the front desk—are ready to help weary travelers rest easy. But there’s one catch: the elevator only starts from the first floor, and a short flight of stairs is unavoidable to reach it. It’s all spelled out clearly, everywhere from the hotel’s website to every booking site you can imagine. What could go wrong? Oh, dear reader—just wait.

Road Rage Meets Its Match: How One Passenger Turned the Tables on a Reckless Company Van Driver

Car swerving on motorway to avoid collision with a van, showcasing risky driving behavior.
A tense moment captured in this photorealistic image, illustrating the dangers of bad driving on busy motorways. This scene reflects the unexpected challenges faced when navigating traffic, especially with family on board.

Picture this: It’s a rainy day, your family is cruising down the motorway, everyone’s a little tense thanks to the weather, but you’re just trying to get to your destination in one piece. Suddenly, chaos erupts—a car swerves dangerously close, your mom (the hero behind the wheel) has to react fast, and in the blink of an eye you’re dodging calamity. But the drama doesn’t stop there. Enter: The Van Man.

Punched, Shot At, Stabbed, and Set on Fire: The Wild Work-Life Misadventures of 'Kevin'

Cartoon-3D illustration of a man getting playfully punched in the ass by his wife at work, capturing a humorous moment.
In this vibrant cartoon-3D scene, our protagonist Kevin experiences an unexpected yet humorous moment at work as his wife playfully punches him in the ass, setting the stage for a memorable story about their quirky adventures.

Some people live life on the edge. And then there’s Kevin, who seems to have launched himself off the cliff, bounced off every jagged rock on the way down, and somehow limped into work the next day—smiling. If you’ve ever wondered just how much chaos one person can attract, allow me to introduce you to the legend known on Reddit as “punched in the ass guy.”

This Kevin is not your average “oops, I microwaved foil” kind of klutz. No, his résumé reads more like a deleted scene from a Coen Brothers movie: repeatedly punched (by his wife), stabbed (also by his wife), set on fire (multiple times), and shot at (with only a hoodie for armor). And yet, he soldiers on—cracked teeth, singed eyebrows, and all.

When Kevin Met Windows: The Hilarious Tale of a POS System Meltdown

Kevin looking frustrated at a computer, symbolizing the struggle of adapting to new technology in IT.
In this cinematic scene, Kevin grapples with the challenges of modern technology, highlighting the generational divide in IT skills.

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.

Clocked Out, Cashed Out: The Hotel Paycheck Fiasco That’ll Make You Double-Check Your Next Deposit

Frustrated worker looking at paycheck delay on a smartphone, cinematic style, capturing workplace stress.
In this cinematic depiction, a frustrated worker stares at their smartphone, grappling with the stress of a delayed paycheck. The image perfectly encapsulates the anxiety many face when technology fails them at work.

If you’ve ever worked a job where your paychecks are as reliable as a hotel Wi-Fi signal at peak check-in, you’ll feel a special kind of kinship with u/boltthepei’s recent saga from r/TalesFromTheFrontDesk. Imagine this: you’re used to your direct deposit landing in your account a day early (score!), your schedule is as predictable as the sunrise, and then—thanks to a glitchy clock-in app and some “hands-off” management—your hard-earned cash is suddenly floating in payroll limbo.

It starts like any other shift, but ends with a maddening lesson in modern payroll roulette. Strap in, hospitality heroes—this is a tale of vanishing hours, missing money, and management that’s about as responsive as a broken vending machine.

Twenty Years Later, Karma Arrives in the Mail: The Chilling Power of Petty Revenge

Cartoon 3D illustration of a family facing a cold neighbor in a rental house community.
This vibrant cartoon-3D image captures the tension between a new rental family and their unfriendly neighbor, setting the stage for a tale of community and resilience.

There’s a special kind of satisfaction in delivering justice—especially when it’s wrapped in a Hallmark envelope and arrives two decades late. We’ve all had “that neighbor”—the one who turns a smile into a sneer the second you’re not looking. But what happens when their frosty attitude finally gets its comeuppance, courtesy of a long memory and a well-timed greeting card? Welcome to the saga of “A Note Best Served Cold”—a Reddit petty revenge story that’s equal parts hilarious, relatable, and oh-so-satisfying.

Imagine this: You move into a lovely community, full of friendly faces and neighborhood BBQs. But next door, the Queen of Exclusion reigns. She’s got a smile for the HOA president and a cold shoulder for anyone who doesn’t fit her picture-perfect mold. Your only crime? Being a renter. The offense? Unforgivable, apparently.

When DIY Dreams Go Deep: The Saga of Kevin and the Rectangle Hole

Anime illustration of a quirky man named Kevin dreaming about building a pool in his backyard.
Dive into the whimsical world of Kevin, a man with big dreams and even bigger misadventures, as he imagines his dream pool in this vibrant anime-inspired scene!

Some people are born with a toolbox in their hands and blueprints in their hearts. Others… well, let’s just say their best-laid plans are best left unlaid. Today, we dive into the unforgettable misadventures of “Kevin and the Pool,” a story straight from Reddit’s legendary r/StoriesAboutKevin—a place where common sense goes to vacation and never returns.

Meet Kevin: a man whose confidence is matched only by his lack of actual construction skills. His tools? Enthusiasm and a shovel. His canvas? The backyard of a house he inherited, and a dream—oh, what a dream!—of having his own pool. What could possibly go wrong?