21 Hilarious Microsoft Windows Fails

Microsoft Windows is notorious for its nonsensical error messages and weird fails. Here are some of the best.
Donovan Alexander
Micosoft Windows errors are endlessly funny.Seigo1224/YouTube

Even the biggest Apple fans have had to use Microsoft at some point, whether at work, your local library, or school. No one has escaped the insanity of repeated error messages and unintuitive pathways.

But whether you love it or hate it, Microsoft Windows has served up some of the funniest fails the internet has ever witnessed. Read on as we take you down a rabbit hole of comedy proudly brought to you by Windows. Microsoft failures can be entertaining. 

1. Well failed

Failing successfully seems to be a cheerful trait of Windows.
Source: U/3Z/Reddit/Imgur

Windows seems to really be into positive reinforcement, even when they fail they do it really really really well. 

2. Shut down Windows!

Windows fails pop even at sporting events.
Source: DelitePlays/Reddit/Imgur

There is something particularly nasty about a  message that tells something went wrong when it is already too late to do anything about it. It is even worse when the message is broadcast to a stadium of people.

3. Where is the 'any' key?

21 Hilarious Microsoft Windows Fails
Source: webhatti

How many times do you think Windows support has gotten a call from someone just unable to find the 'any' key? 

4. Was this helpful?

Windows asking if there nonsensical error messages is helpful, is simply not helpful.
Source: MrCurlyz 6/Reddit/Imgur

There are lots of questions to ask here, but the main one is what does this error message mean? A speech bubble? A revolutionary square? No matter how you interrupt it we can almost guarantee no one found it helpful. 

5. Windows crushes time travel

Time is no match for the mighty Windows
Source: avapoet/Reddit/Imgur

Umm, what lol? Seems like Windows has really got a hold on the time-space continuum and is pushing us into the future and the past simultaneously. Hold on for this exciting ride. This sits on the top of our list of Microsoft failures

6. Trouble means trouble

Windows troubleshooting can feel like an alternative reality of pain.
Source: AemsOne/Reddit/Imgur

When your troubleshooting causes trouble you know you are in trouble.  This is a classic example of Windows chasing its tail like a lost dog. 

7. Trust me I'm Windows

Would you trust Windows?
Source: Lawpoop/Reddit

Don't trust Windows when they tell you everything is ok.  Getting this message can only mean something terrible has happened. This is probably worse than the Microsoft blue screen of death. 

8. Windows gets sentient

21 Hilarious Microsoft Windows Fails
Source: Seanbearu/Reddit

Even Windows doesn't think updating to the latest version is a good idea. Seems like there is some common sense in there somewhere. 

 9. To update or not to update

When updating becomes a philosophical question.
Source: KillJoy 17/Reddit

 Windows inner voice questions if it should push for the update or not.  Who will win?

10. Everything looks perfectly ngymadly to me

Who has taken over Windows and what do they want?
Source: LordKronos/Reddit

Has Lord Voldemort snuck into your Windows? Because it really doesn't seem like everything is 'ngrmadly' to me. 

11. Sneaky FireFox

Windows is forever trying to push you around.
Source: RedditMan44

Windows has a bad rep for pushing their products on you. Here is one of their sneaky ways to get you to fully commit. 

12. If all else fails: delete

Even Windows thinks deleting itself is a good idea.
Source: i_post_tech_articles/Reddit

Sometimes it seems Windows just gets sick of well, Windows.  When your computer offers to delete its operating system, run. These Microsoft Windows fail makes us chuckle

13.  Just sit back and relax

When Windows tell you to calm down.
Source: ShainMemes/Reddit

'This won't take long' said Windows. Three years later your computer is updated, just in time for the latest update. 

14. Just can't

Even Windows gets the blues
Source: Vadell/Reddit

Even Windows gets the blues! This error message will resonate with anyone that has to go to work.

15. Nowhere is safe from Windows

21 Hilarious Microsoft Windows Fails
Source: Pepsistopheles/Reddit

Not even the office water cooler is safe from the probes of Windows and their mysteriously long upgrade times. You are better off with the tap in the bathroom.

16. Stay calm, something happened

21 Hilarious Microsoft Windows Fails
Source: CompiledSanity/Reddit

We don't know what it is, but something happened.  This ominous message from Windows could mean anything from the total system collapse to a successful installation. Your guess is as good as mine. Ok, maybe this is weirder than the blue screen of death

17. You've got time

21 Hilarious Microsoft Windows Fails
Source: TechyV

Get yourself a snack, actually a couple of snacks. Looks like you'll be here for some time.

18. Taking security too seriously

Password security is important, but this is just crazy.
Source: TechChunks

Password security is important, but this is ridiculous. 18770 characters would take about 45 minutes to type!

19. Make space for space

Freeing up disk space to make room to delete things
Source: TechyV

Deleting stuff to make space to delete stuff seems insane, or just very Windows.

20. How small do disks come?

21 Hilarious Microsoft Windows Fails
Source: Mike Hypponen/Twitter

Microsoft doesn't only make operating systems for PCs. They have entered the smartphone market too. But seems like they forgot something about the size of phones...

 21. I've got 99 problems and Vista is one

Vista is a problem even for its creators.
Source: MakeUseOf

Being able to self-reflect and identify the cause of your behavioral problems is really important.  Seems like Windows has this skill unlocked. 

Do you have a favorite Microsoft Windows fail? 

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