The 12 Most Ridiculous Windows Errors of All Time
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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” 6 Human Jobs That Computers Will Never Replace 6 Human Jobs That Computers Will Never Replace Read More 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 Why Does Windows Crash? The Top 10 Reasons Why Does Windows Crash? The Top 10 Reasons Oh, great. Another blue screen, boot issue or frozen screen in Windows. Now you have to restart and lose most or all of the work you’d been trying to accomplish. It’s frustrating both because of... Read More , 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:

IE See Information Warning

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 Avoiding Internet Surveillance: The Complete Guide Avoiding Internet Surveillance: The Complete Guide Internet surveillance continues to be a hot topic so we've produced this comprehensive resource on why it's such a big deal, who's behind it, whether you can completely avoid it, and more. Read More .

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?

Windows Program Reporting Error
Image Credit: Gizmodo

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 How to Fix Error Code 0x800F081F in Windows 10 How to Fix Error Code 0x800F081F in Windows 10 Error code 0x800F081F is one of four possible error codes that all point to the same underlying issue. Here's how to troubleshoot and fix it. Read More  or, worse, a BSOD like SYSTEM_SERVICE_EXCEPTION How to Fix the System Service Exception Stop Code in Windows 10 How to Fix the System Service Exception Stop Code in Windows 10 The System Service Exception error in Windows 10 includes a variety of causes. Here's why it happens and how to stop it from happening again. Read More .

3. This Might Take a While

Whenever you move some files 5 Ways to Transfer Files From One Computer to Another 5 Ways to Transfer Files From One Computer to Another Need to transfer files between separate PCs? Here's how to do that quickly and easily, using both hardware and software. Read More , Windows provides a helpful dialogue box to estimate how long the transfer will take. Sometimes, it’s not exactly accurate.

File Transfers on Windows Vista
Image Credit: TechBlog

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:

Windows Error Success
Image Credit: E A via Flickr

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:

Unspecified Security Flaw
Image Credit: Zusch Login

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 5 Ways to Delete a File in Use in Windows 5 Ways to Delete a File in Use in Windows Windows Explorer thinks the file you're trying to delete is still open, but it's not? Locked files are a common problem. Fortunately, it's easily solved in most cases. Read More , but this one is bizarre enough to raise some eyebrows. If you try to delete a file, Windows may bark at you with this:

Error Deleting Files
Image Credit: TechV.com

That’s funny, Windows. I was trying to delete a file to free up disk space 6 Ways to Free Up Space on Your Windows Computer 6 Ways to Free Up Space on Your Windows Computer Clutter can be a big downer on productivity. Over time, files get lost, programs go unused, and suddenly, your once spacious hard drive is packed with useless things and you have to clean it up.... Read More , 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 How to Create a Strong Password That You Will Not Forget How to Create a Strong Password That You Will Not Forget Do you know how to create and remember a good password? Here are some tips and tricks to maintain strong, separate passwords for all of your online accounts. Read More , 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.

Error Long Password
Image Credit: TechChunks

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:

Error Failed Shutdown

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 Is Windows Taking Forever to Shut Down? Try This! Is Windows Taking Forever to Shut Down? Try This! You’re just turning your PC off; how hard can it be? Shutting down is a complex process and much can go wrong. If your Windows 7, 8.1, or 10 gets stuck, check out our troubleshooting... Read More . 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.

Problem Caused by Vista
Image Credit: Quora

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:

Something Happened Error
Image Credit: reddit

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 6 Common Windows Upgrade Issues & How to Fix Them 6 Common Windows Upgrade Issues & How to Fix Them Upgrading Windows 10 can cause a number of complications. We show you what to watch out for and how to prevent or fix issues. Read More 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 Oops, I Did It Again: 7 Keyboard Shortcuts Users Keep Hitting By Mistake Oops, I Did It Again: 7 Keyboard Shortcuts Users Keep Hitting By Mistake It happens even to the most experienced of users: the accidental keyboard shortcuts. No matter how often you use your computer, weird things can start happening when you’re going too fast, when you lean on... Read More , and gives you a recommendation to fix this?

Keyboard Error
Image Credit: Goliath

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 Why You Should Upgrade to Windows 10 Mobile and How to Do It Why You Should Upgrade to Windows 10 Mobile and How to Do It Windows 10 Mobile has finally been released to the public. Provided your phone is supported, you should upgrade. Here's everything you need to know about upgrading from Windows Phone 8.1 to Windows 10 Mobile. Read More sometimes came across this error:

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 How to Fix the WHEA Uncorrectable Error on Windows 10 How to Fix the WHEA Uncorrectable Error on Windows 10 Some Windows crash errors are more cryptic and therefore more difficult to troubleshoot. The WHEA Uncorrectable Error is one of those. Read More 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 3 Windows 98 Bugs Worth Revisiting 3 Windows 98 Bugs Worth Revisiting Is it just nostalgia that keeps me attached to this OS, or was Windows 98 actually worth remembering? This operating system released 15 years ago had its ups and downs. Critics have been pretty harsh... Read More 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?

Explore more about: Troubleshooting, Windows 10, Windows 7, Windows Mobile, Windows Phone, Windows Vista, Windows XP.

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  1. mike
    December 14, 2017 at 10:48 pm

    I know this is an aside, but spot lights a facet of this whole message topic.

    I was working at a bank, testing their new and improved teller software and I discovered an error message that was a long line of profanity. There is a little history here. When I worked in the software industry it was a challenge for programmers to try and slip in "Easter eggs." Little artifacts a programmer could point to as an ego boost. One example was a guy programmed a little golf putting green flag in certain areas of a macho kill them all game program. God mode in games started when a programmer forgot and left them in a game, they were intentionally inserted to give testers a helping hand to test certain features originally and were supposed to be removed. When the game industry found out the users loved them these "features" became part of newer games.

    Now, back to the profane error message. While it was technically accurate the nature of the language was....at best lewd, well the programmer was fired and the message changed. I suspect he didn't think it would be found until after the program was issued and he was long gone. I don't know if he had a beef with management or just bad taste, but it did garner a lot of laughs in the test department. You know bankers are a real "button down" lot.

    So, when you go about your daily chores, look closely at "messages" and look for artifacts, they are still there and even in new software there are "cheeky" programmers inserting them. Often the messages have hidden meanings and the logos have inserts that when expanded will yield a cartoon character and all sorts of other things. All manner of things can be found with a little creative digging, such as odd key strokes etc. In one place what appeared as an extra period was a cartoon of the "keep on trucking guy."

    So stay sharp, you may find one of these sly artifacts or off key messages.

  2. John K.
    November 21, 2017 at 2:41 pm

    My favorite of all time was "Error: This error should not have occurred."

  3. Kendrick G.
    December 1, 2016 at 4:08 pm

    The "Keyboard Not Detected" error isn't actually that dumb. If it's a false alarm, you can just press a key and it'll know your keyboard is connected; if it's not, then you need to plug your keyboard in.

  4. Jeff B
    November 29, 2016 at 2:35 pm

    My favorite two windows errors messages:

    1) Any network related error messages that ask the user to get help from their system/network administrator. While that is fine for the office PC (where you typically have an an IT person/staff), but it is stupid for the home PC that you are trying up out of the box [Sorry, I don't have any children to serve as Tech Support]. I have go to the bathroom and ask the person in the mirror what to do.

    2) Any Windows error message that presents you with a long hexadecimal error number and tell you to go online and look up the error code to determine how to resolve it. How is that useful? The best example of this was when I setting a laptop to run the Win10 Technical Preview (Win 10 Beta). I was presented with a blue screen with an hex number and instructed me to look up the code online. Fortunately, I had other computers at home because the error code ended up indicating that the computer was not able to connect to the internet due to a networking configuration issue. ... If I only had one PC at home I can only wonder how I would be able to figure that out based on the hex number displayed on the screen :(

    • Ben Stegner
      November 29, 2016 at 4:47 pm

      I agree, and the top one is frustrating when you ARE the IT person! Sometimes you try every little thing and still get stupid errors that tell you to contact support. That doesn't help when you are support.

      Not having two computer can cause a big problem when troubleshooting, that's for sure.

  5. Robert
    November 28, 2016 at 12:29 am

    you overlooked on #7. typos, Since you can't see what you are typing. So figure 18 HOURS if you are lucky to log in.
    I had just the opposite problem with windows 95 running on a virtual machine. You touch a key and 50 of them pop up in the password box. Login bypasses all the settings you can enable to slow keystrokes down.

    • Ben Stegner
      November 29, 2016 at 4:46 pm

      Ha, I guess I assumed that everyone would be a perfect typist when typing in 18,000 characters!

      Oh, that's weird. Were you able to log in like that?

  6. Andrew
    November 27, 2016 at 10:16 am

    For:
    "6. Cannot Delete a File, Please Delete Files"
    I am pretty sure that this happens when Windows wants to copy the desired files to the recycle bin. As there is not enough space on the drive to copy the file there then the operation fails.

    And for:
    "9. Vista Is a Problem"
    The error states that Windows Vista has reported an error with a driver. This means that Windows Vista has caused the problem but the resolution involves installing a driver suitable for Windows Vista as stated in the window...

    • Ben Stegner
      November 27, 2016 at 6:15 pm

      I think you're right, but the fun is in the wording for #9.

    • Doc
      November 29, 2016 at 8:40 pm

      That can't be true, since every drive letter (partition) has its own "Recycle Bin" so that files don't have to be moved from one drive to another to recycle them (which might take the 120+ years to move. :) Windows combines all its "recycle bins" into one "bin" so that you don't have to go to each drive letter to empty it.

  7. Rikaz Sheriff
    November 26, 2016 at 6:40 pm

    OMG this was hilarious and really took me back to the 90s.

    • Ben Stegner
      November 27, 2016 at 6:15 pm

      There are lots of great errors from the '90s, but plenty from recently, too!

  8. Andrew
    November 25, 2016 at 11:59 pm

    NT4 once told me you must change your password, then when I went to change it, told me you do not have the authority to change your password.
    While I support both options, surely they're MUTUALLY EXCLUSIVE.

  9. Bruce Epper
    November 25, 2016 at 10:42 pm

    Number 6 makes sense. That message only shows up when files are going to be dumped into the recycle bin. In that case, a *copy* of the file is put into the recycle bin then the original is deleted. The disk cleanup button is there and works because it deletes the files rather than putting them in the recycle bin. Using shift-delete will always avoid this message.