Computers and humans are so different. While computers are infinitely faster at processing information, they run into trouble if they try to stray from their course. These “fast idiots” contrast to people, who can’t think as fast as machines but can adapt much more easily.
These relations have produced some hilarious situations where novice users failed to grasp the basics of using Windows. On the other side of this are error messages. When a computer runs into an unexpected scenario, it usually throws up a message box for the user to review.
While these can provide information about real issues, a lot of the time they’re paradoxical, funny, or just plain stupid. Let’s enjoy a look at some of the silliest and stupidest error messages that Windows has produced.
1. The Internet Has More Users Than Just You
Anyone who’s used the internet for more than five minutes knows that most activity online isn’t private. That doesn’t stop internet Explorer (IE) from pointing out the obvious, though:
This error typically pops up upon a new IE installation. You’ll usually see it when searching Google or Bing for the first time. As it kindly points out, when you put something online, some other user, somewhere, might be able to see it. Imagine that! Thankfully, you can check the Don’t show me this message box and IE will spare you the reminder in the future.
This error might have been more fitting in the early days of the internet, but it continues to lurk around in IE nowadays. It’s still important to stay secure online, so be sure to review the guide to avoiding internet surveillance.
2. Windows Error Reporting Will Report an Error
Whenever a program crashes in Windows, it usually asks you to submit an error report so that you can pretend that Microsoft is looking for a solution to your exact problem. However, what happens when the error report runs into an error?
So now, the program reporting the error has hit an error, but don’t worry. Windows will let you know if a solution pops up. How it will reach that solution is unknown, though, since an error is preventing it from finding that solution. Hopefully, we don’t hit another error or, worse, a BSOD like SYSTEM_SERVICE_EXCEPTION.
3. This Might Take a While
Whenever you move some files, Windows provides a helpful dialogue box to estimate how long the transfer will take. Sometimes, it’s not exactly accurate.
Don’t worry, your gigabyte and a half of data will be all moved in just over 127 years. Hopefully, you’ve designated a successor to oversee its completion, although it’s more likely that the operating system will just stop working before then. More likely even, Windows will interrupt it with an update and restart.
4. False Alarm
There are enough error messages in the world that provide info about actual problems. This particular message isn’t satisfied with that, though, and instead gets you all worked up for nothing:
Most people will see the Error header, accompanied by the big red X, and assume that something went wrong. But don’t worry! We just wanted to give you a scare — and let you know that everything was successful. Why even have a message box about a success in the first place?
5. Unspecified Potential Security Flaw?
There’s nothing quite like an error message that’s so vague and unhelpful that a user has no choice but to ignore it. Here’s one such message:
What is the average person going to do with this? Not only is the security flaw unspecified, but it’s only a potential flaw. Does that mean by clicking Yes I’m rolling the dice on my security? Messages like these result in people clicking Yes as fast as possible to clear the annoying box and get back to what they were doing.
6. Cannot Delete a File, Please Delete Files
It’s not rare to see errors when deleting a file, but this one is bizarre enough to raise some eyebrows. If you try to delete a file, Windows may bark at you with this:
That’s funny, Windows. I was trying to delete a file to free up disk space, but now you’re telling me I need to free up disk space by deleting other files. Why we can’t delete this specific file to free up that space is a mystery nobody knows.
7. We’re Going to Need a Longer Password
We know that a longer password is more secure, but this is taking it a bit too far.
Some Windows 2000 users found that the OS wouldn’t accept anything less than an 18,770 character password. Don’t even try to sneak that 18,760 character password by Windows.
Even better, Windows wanted to enforce security by making sure that this mega-password was different from the last 30,689 passwords. What are the chances of duplicating over 18,000 characters (about 9,300 words!)? Can a password manager even hold a password that long? One reddit user estimated that it would take about 45 minutes for an average typist to enter this many characters.
As explained by Microsoft, this arose from a bug with MIT Kerberos domain authentication, which they fixed with Windows 2000 Service Pack 3. Microsoft also helpfully pointed out that “the number of required characters changes from 17,145 to 18,770 with the installation of SP1.” This provided a much-needed explanation to people who were wondering why they suddenly had to add an extra 1,625 characters to their passwords.
8. We Can’t Open Programs When Shutting Down
Software developers were creating error messages so awful that Microsoft had to step in and create a guide to effective error messages. The first “Hall of Shame” message they criticize is this:
This error is a perfect blend of unnecessary and annoying. It lets the user know that a piece of software couldn’t launch because Windows is shutting down. Of course, the user initialized the shutdown, so they don’t care that a program can’t launch. Even worse, this message prevents Windows from shutting down until the user closes it, so if you walk away, your computer could be sitting there waiting to shut down for hours.
The best option would be to avoid an error message altogether. We’re glad that we can take the opportunity to poke fun at this one, though.
9. Vista Is a Problem
Windows Vista wasn’t exactly the finest version of Microsoft’s operating system. While it’s a common joking point among computer users, we wouldn’t expect Microsoft to say anything too bad about Vista.
But lo and behold, here’s Windows letting us know that Microsoft Windows Vista caused a problem! The window lets you know that a solution is available that will solve this problem, but the best solution was probably to stop using Vista.
10. Something Happened
Here’s one that’s more recent. When upgrading to Windows 10, you might have encountered this helpful message:
Just in case you weren’t sure if something actually happened, it’s both the title and body of the message. We can’t imagine how this message was helpful for the development team, let alone for the user. Was the “something” our name being chosen in a giveaway?
Thankfully, you can fix this upgrade issue with relative ease.
11. No Keyboards Here
You’ve probably seen “press any key to continue” messages at times. Usually they’re not a problem. But what happens when Windows recognizes that you don’t have a working keyboard, and gives you a recommendation to fix this?
Er, if the keyboard isn’t responding, how will you know that I’ve pressed a key? Is this a test to see if I’m gullible? I’m not going to press anything.
12. Insert Disc Into Windows Phone
This one isn’t technically a Windows error since it occurred on a Windows phone, but it’s still pretty funny. While normal users probably wouldn’t ever hit this error, those tinkering with their Windows Mobile devices sometimes came across this error:
— mikko @ #slush19 (@mikko) January 11, 2013
You might see this error on a Windows desktop installation with corrupted files, but it’s the recommendation that’s funny. Does my phone have a slot for discs, or do I need to purchase an adapter for that?
Error Loading Errors
It’s fun to joke about computers being silly. These errors might be frustrating when you encounter them, but when you take time to think about what they (fail to) tell you, the humor comes through. Hopefully, developers can learn from these and create error messages that aren’t as cryptic or useless.
Did you know that you could bypass the Windows 98 login screen through a printer? Check out throwback Windows 98 bugs for more laughs.
We’re sure that there are many more errors that could be added to this list. What are the funniest errors you’ve encountered in Windows?