21 Hilarious Microsoft Windows Fails
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

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

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?

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?

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

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

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

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

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

Windows inner voice questions if it should push for the update or not. Who will win?
10. Everything looks perfectly ngymadly to me

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

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

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

'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! This error message will resonate with anyone that has to go to work.
15. Nowhere is safe from Windows

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

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

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 ridiculous. 18770 characters would take about 45 minutes to type!
19. Make space for space

Deleting stuff to make space to delete stuff seems insane, or just very Windows.
20. How small do disks come?

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

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?