40 Hilariously Cringe Work Fails Will Make Your Workweek Look Tolerable By Comparison

Here’s to a hopefully less cringeworthy start to your workweek. If you need a good laugh or a reminder that your job isn’t so bad, then you’re in for a treat. We’ve dived deep into the depths of Reddit to bring you some of the funniest, most cringe-worthy work fails ever captured.

These 40 photos are a testament to the humorous side of work disasters, from office pranks that turned hilariously wrong to outdoor work fails that are so bad, they’re good. Each image, handpicked from Reddit, is guaranteed to make you laugh, cringe, and maybe even feel a little bit better about your own workday mishaps.

So take a break, scroll through these funny work fails, and thank Reddit for the much-needed comic relief.


1. “Nice Job”

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2. “The Truck Driver Who Forgot To Release The Bolts Of The Container In Ashdod Port This Morning”

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3. “Guess Someone’s Gonna Be Late For Work”

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4. “Overnight Coworker Sent Me This Last Night”

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5. “My Company Is Sending Work From Home Employees New Laptops. I Somehow Ended Up With All Of Them”

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6. “Damn Near Cut My Dong Off Today… Two Things That Stopped It From Happening: 1) My Big Guts 2) My Small Wiener”

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7. “A Truck Carrying A Tank Of White Paint Dropped It On The Road”

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8. “My Coworker Left His Phone Under The Industrial Paper CutterMy Coworker Left His Phone Under The Industrial Paper Cutter”

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9. “I Got A $0.25 Raise This Year Which Absolutely Is Not Keeping Pace With Inflation. And Then I Get To Walk Into Work And See The Owner’s New Toy”

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10. “I Find It Amusing How The Forklift Driver Must Have Been Staring Directly At The ‘Do Not Stack’ Sign”

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11. “This ‘Gift’ For Employee Appreciation Day”

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12. “Hubby Was Unemployed For 9 Months. Finally Landed A Job That’s Not Temporary Or A Contract Gig. 5 Minutes After Clocking In, He Trips On Some Carpet And Breaks His Leg”

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13. “Coming Into Work To Discover That Someone Left The Ice Machine’s Door Open Overnight”

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14. “The Restaurant I Work At Occasionally Hosts A Drag Brunch. This Past Week We’ve Been Receiving Calls Threatening To Protest Against An Upcoming Brunch. This Vandalism Happened Overnight”

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15. “Someone Brought Cheerio Donuts Into Work Today”

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16. “I Left My Job Shortly After Receiving This Prize For My Good Work”

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17. “Knelt Down To Get A Ping Pong Ball From Under The Table At Work And Heard A Little Rip”

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18. “Someone Reported Me To HR For A Suspected Drug Use, Saying I Must Do Them In My Truck While At Work. HR Opened An Investigation. This Is Literally Powdered Sugar From The Fried Oreos”

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19. “I’ve Had To Take A Couple Weeks Off Work Because I’m Allergic To Part Of My Job”

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20. “My 6-Feet Husband Started A New Job, This Is The Uniform They Gave Him. And It Is My Fault As I Took The Measurements. Even His Boss Ended Up Laughing”

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21. “After Working 3 Positions And Managing 20 Employees, Here’s My Work Christmas Gift”

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22. “Had A Leak Develop In Our Laboratory This Morning. Nobody Was On Campus To Catch It So There Was 4 Inches Of Standing Water And Countless Ruined Pieces Of Equipment”

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23. “Happened On My Way To Work”

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24. “What I Was Greeted By This Morning At Work, First Day After Christmas Break”

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25. “Someone At Work Perfectly-Ripped My Husband Out Of The Wedding Photo On My Locker. There’s No Way This Was Accidental”

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26. “This Glove I Put On At Work Before Going Into Surgery Had Dozens Of Pin Prick Holes In The Fingers. The Entire Box Was Like This”

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27. “The Toilet Paper At My Work Is So Cheap It Has Splinters”

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28. “Car Crashed Into My Bakery At Work, Old Lady Accidentally Hit Her Gas Instead Of Brakes”

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29. “This Mirrored Ceiling In Our Bathroom At Work”

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30. “A Guy At My Workplace Uses This Bathroom Every Day, And Each Day He Leaves His ‘Nest’ Behind. It’s Disgusting And Disrespectful To The Cleaning Staff”

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31. “I Work In Pharmaceuticals, This Was A Very Expensive Mistake”

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32. “My Father Was Almost Pulled Into A Lathe While Working. Only Stopped By His Clothing Being Tangled”

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33. “I Have Multiple Pairs Of Work Shoes And Today I Brought 2 Left-Foot Shoes”

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34. “Eggsactly What He Feared Would Happen”

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35. “My Colleague Did Not Calculate The Height Of The Truck, And How Low The Bridge Was”

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36. “I Have A Costco Box Full Of These At Work, Just Ate One Yesterday. This Entire Bar Was Infested With These… Things”

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37. “I Got The Chopping Board Stuck In The Sink At Work”

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38. “My Boss Installed A Water Dispenser Yesterday. This Morning We Got Into The Office To This”

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39. “We Can Cut Into The Concrete Here They Said. It Will Be Fine They Said”

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40. “The Water Coming Out Of The Kitchen Faucet At Work. I Work At A Restaurant”

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Read more40 Funny Work Memes Every Underpaid, Overworked Employee Will Relate To This Week

Nate

Nate Armbruster

When he's not doomscrolling Twitter or writing for Pleated-Jeans, Nate Armbruster writes jokes—and then tells them on stage as a stand-up comedian, where he can watch audiences (hopefully) laugh in real-time.