The 6 Biggest “Oops!” Moments in Microsoft’s History

We’ve grown to appreciate the success of Microsoft’s Windows 7, but no one – not even Microsoft fanboys – can say that the company has actually done its homework before releasing every product. Some would say that Microsoft has made too many mistakes to continue as a prominent company, but there are those with a more realistic argument that every company has its share of blunders. We’ve already discussed Microsoft Bob in a previous article, so we’re not including it in today’s list. We’d like to say that this was perhaps the biggest failure in Microsoft’s history, but we can’t be the judge of this. We’ll leave it up to you to decide. Have a look!

1. DOS 4.0, or MS-DOS


Yeah, we know that the Disk Operating System (DOS) wasn’t invented by Microsoft, but they made their own version of it to suit their file system and structure. Released in 1988, MS-DOS was a very strong improvement over previous versions of DOS. Even with the improvements, Microsoft introduced new bugs into the system, making it difficult to operate and frustrating for most people who used this software on a daily basis. First of all, hardware communications were terrible. The RAM component was highly volatile, making innocent people lose all of their data at times that they tried to access files larger than 32 MB. The disk corruption implicated would cause users to lose everything, with an inability to recover.

2. Internet Explorer


There’s a reason why people call Internet Explorer “one of the most amazing tools to download [insert other browser here].” First outdone by FireFox, and later outdone by Google Chrome, Internet Explorer has become quite an unpopular application for users of Microsoft Windows.

The most important, and perhaps most obvious, reason Internet Explorer was a failure has to do with security measures implemented in its code. It has more lax security than other browsers do, allowing ActiveX controls to perform acts of atrocity that allow a user to easily fall victim to browser hijacking and infections that don’t involve any action on the user’s part. In some cases, you’re on the chopping mill as soon as you enter a website.

If you’re a web programmer, you’ve probably encountered times when everything on the site you’re working on works in every browser except Internet Explorer. That’s because its interpreter doesn’t completely conform to the World Wide Web Consortium (W3C) standards.

There’s a reason why a large number of people use Google Chrome, FireFox, Safari, or Opera.

Editor note: The above claim is best suited for IE 6, 7 and 8. IE 9 (and 10) has been doing well since its release. and is adhering more closely to the Web standard.

3. The Zune


Here’s a fight that Microsoft gave up on. The Zune was supposed to be the “iPod Killer” that would revolutionize the MP3 player market. Unfortunately for Microsoft, the iPod Touch already came out and, well, revolutionized the MP3 player market. To make things worse, Apple was already preparing to release the iPhone while the Zune was being developed.

That left the Zune behind as an intriguing toy and an embarrassment to the company. The Zune Marketplace also bordered on a failure, and was discontinued, soon to be replaced with a service for XBox Live.

4. Windows 2000


A lot of people like to rag on Microsoft’s Windows Millenium Edition (ME, or otherwise called “Mistake Edition”), which was rightfully named the 4th worst tech product of all time at PC World magazine. However, many people underestimate the potential of Windows 2000 in taking that spot, as the operating system had many of the core issues that Windows ME had. Not only was the operating system released too close to the release of Windows ME, but it also had tons of security vulnerabilities that Microsoft had to patch up.

A total of four service packs were officially released for Windows 2000, and one more service pack came out unofficially. The service packs chiefly addressed all the holes this operating system had in it, making it look like a lump of Swiss cheese. To top it off, the United States Department of Homeland Security was compromised due to one of these security flaws, leading to a major media scandal about Microsoft’s incompetence at the time. Other organizations falling victim to this were the New York Times, CNN, and ABC.

5. Microsoft’s Failure to Acknowledge Linux as a Major Driving Force


Linux is a competitive operating system, period. It’s competitive not only for the fact it’s free, but it’s also a very versatile OS that allows you to make modified versions of it and redistribute them as you’d like. Microsoft did not consider this a very big selling point for the OS, and thought that Windows will remain the dominant operating system on the market regardless. A little after that attitude became clear, Linux became an operating system used in up to 85 percent of all the world’s super computers.

Linux represents all that is altruistic and collective in technology and innovation. If Microsoft wants to make a significant impact and continue to control a big piece of that pie, it will have to move its act into Linux. So far, we understand that Microsoft is beginning to jump into Linux development to help encourage interoperability between the two operating systems within a server environment.

Hopefully, Microsoft can also build some bridges by involving itself more deeply in the Linux project.

6. Windows Vista


Granted, Windows Vista actually created lots of improvements in security and resource management, but it exaggerated a tad.

First of all, Microsoft introduced User Account Control (UAC, also known as “Useless Account Control”).

Then, we had Superfetch, which was something carried onto Windows 7, but less volatile. Superfetch would pre-fetch the memory necessary to run a program before you even started it. This reserves a space for programs you use frequently so that they would be able to run very quickly. While that was the goal, nothing was accomplished in Windows Vista short of making the computer run worse than it would have with Windows XP, even on higher-performing machines using the recommended system specifications.

Lessons Learned

While many people would argue that Microsoft is still the company it was in 2007, others believe that it has gone in another direction with Windows 8. Despite the fact that its interface design is a little rough around the edges, the core of the operating system is much stronger than Windows 7. We can certainly hope that fewer of Microsoft’s ideas hit the Recycle Bin in the future.

Is there anything we didn’t mention that you think you can contribute? Let us know in the comments section below!

Miguel Leiva-Gomez Miguel Leiva-Gomez

Miguel has been a business growth and technology expert for more than a decade and has written software for even longer. From his little castle in Romania, he presents cold and analytical perspectives to things that affect the tech world.


  1. Regarding Vista, I’d recommend this article:

    “Vista Annoyances Resolved” is written by Koroush Ghazi and documents the misconceptions over Vista and how to solve these ‘problems’. But more importantly, he compares the release of Vista to XP and shows that XP garnered exactly the same criticism as Vista did when it was released over a decade ago. Having a go at Vista has been the latest fashion for members of the FUD Factory for a long time now, but if you actually check out some stats and facts you’ll see that Vista was definitely not a ‘tech flop’ as it seems to be in the minds of users relying on bloggers for their information.

    1. Vista was a component that many people upgrading from XP couldn’t really handle. I’ve used Vista for a long time and was actually very happy with the OS. However, I couldn’t deny that even 4 GB of RAM wouldn’t satisfy its hunger, even in a 32-bit environment and barely running any applications. The most important part of Vista was its ability to fetch up applications on the fly and its increased ease of use. However, Windows 7 was set out to fix all that was wrong in Vista, as there were several people who refused to upgrade because of how they’ve seen other machines not get along with the OS.

  2. Regarding the first item, even the title is wrong. The first MS-DOS was released in 1982, and MS-DOS 4.0 was released in 1988. It was primarily the work of IBM.

    I have no idea what this might mean: “hardware communications were terrible. The RAM component was highly volatile…” Huh?

    1. It was referring to the fact that MS-DOS 4.0 was released in 1988.

      Back in those days, there was a RAMDisk. MS-DOS 4.0 didn’t support a file system in that component larger than 32 MB. Does this clear something up? I’m not sure what’s so confusing about that.

  3. Wow what a terribly researched article. The bulk of the facts are inaccurate and the conclusions fatuous. For example I can assure you MS never underestimated Linux (apple, google, Firefox yes, but linux no). Windows 2000 was a great server and workstation OS far superior to NT 4. Service packs are std fair for all products, one could sayapple does them all the time and charges for them… Oh and zune marketplace is alive and we’ll on my PC and Xbox and windows phone.

    1. Currently, the CEO of Microsoft is Steve Ballmer. He calls Linux a “cancer.” So much for never underestimating Linux.

      Windows 2000 was a wonderful OS, which is why it had to have thousands of fixes released for it within the first 3 years of its distribution. These aren’t opinions. Granted, it was a step up from NT4, but it was no XP. I never praised Apple, but yes, Apple has done tons of its own blunders, which is something mentioned in the article.

      This isn’t an attempt to smear Microsoft. It’s simply reflecting on past mistakes the company ITSELF admitted to doing, and going forward with how the company learns from them and evolves.

      The Zune Marketplace, by the way, is still alive, but is to be discontinued soon. The Zune itself is already discontinued. The project has been scrapped, and even Bill Gates mentioned that he is not pleased with how the device evolved. 
      It’s getting rather tiresome to deal with people who think that this is a smear attempt. If anything, Microsoft is a pretty steadfast and sturdy company for overcoming some of these blunders. I actually laud their effort and call both Apple and Microsoft pinnacles of today’s technology in many occasions. None of the companies deserve anything but the utmost respect for what they have accomplished, sometimes even mutually.

  4. I think you could definitely add the irritating ribbon interface introduced with Office 2007 to the Oops! moments. This has brought only frustration and waste of time due to hard to find ‘advanced’ functions – not to mention the new longer and incoherent keyboard shortcuts. Unfortunately this is in perfect concordance with today’s trend of priviledging shiny looks over usability, with only basic and casual users in mind…

    1. To be sincere, it’s not as big a blunder as other things that Microsoft introduced. We’re talking about system-wide calamities or things that cost the company millions of dollars for nothing. Office 2007, although kind of clumsy, didn’t cost the company its reputation. And to be sincere, I actually love the interface in Office 2010, although I could understand why others would be frustrated.

  5. MS-DOS, only a failure if you didn’t know how to use it. MS-DOS is also the reason for CMD existing on 2000 – W8 (and Power shell on server editions). Imagine a Windows Server 2008 R2 that wasn’t core… waste of power. Most of the MS-DOS commands still exists in today’s Windows CMD versions and has come in handy for me on more occasions than I dare count.

    IE, complete failure if they stopped evolving it in 2005, they didn’t. They merely paused it. IE 9 (and IEX for W8) has really struck the nail. And you don’t see Mac’s offering another browser at the first start?

    The Zune. I must admit the device in it self being a failure. BUT Zune (application) has really evolved into a powerful cross-platform monster, to the likes that haven’t really been seen before. Before you say iTunes…. not really cross-platform…

    Saying WIN2K is a failure, is the same as postulating Homo erectus was a Darwinian setback. Although WIN ME, was buggy, sluggish and downright wrong, it would still mean the development of a new disk format, the NTFS. Which in term also meant a general update on system specs and the likes.

    MS not recognizing Linux, is a complete heap of nonsense. They are on the top-ten list of contributers.

    Vista is ALMOST a homerun on the failure side. Although it offered the vision of W7 and heralded the implementation of TxF (NTFS 6.0). Windows vista also showed the world what could really be done when using vector grapics that would not congest the GPU (compared to competition). While you where dead-on with Superfetch/prefetch, it still remains as a feature in W7, but it targets much more mundane tasks, such as search features and calls.
    BTW: UAC is what keeps half of the viruses at bay dummy.

    I had my say, and somebody had to say it. I would still like to add, that while much of your criticism is much on-par with the global consensus, much of it is due to mis-information and blind ignorance. It’s not something I’d expect to hear from someone that has (apparently) studied MS. I think Failure and success is a matter of perception.

    But I think we can agree to disagree?

    Ps. Me calling you a dummy, is a case of stating the obvious (like “duh”)

    1. Actually, we are on par with what you said here. Read the article again, my friend :)

      We’re really agreeing with most of these things. I’ve mentioned that Microsoft was the seventeenth in another article on this site. The problem is that Steve Ballmer goes around saying that “Linux is a cancer” and it’s got the entire computing community on a rage fit against MS. In reality, though, Bill Gates has always recognized the validity of Linux in the big scheme of things.

      Zune’s only problem, besides being a piece of hardware that quickly got outdated, was the fact that it wasn’t marketed enough, and was completely phased out by everyone else using their beloved iPod Touch.

      There are still so many holes in W2K, btw, that I just finished using a remote access exploit to get into a test computer just for old time’s sake, even with SP4 installed in it. NTFS was an awesome advancement, though! This article is only dedicated to the oopsy things, but is far from a smear attempt, believe me. It was simply just looking back, laughing as friends, while keeping our eyes on the horizon that waits for us. Microsoft, I feel, will be a huge part of the future of technology for many decades to come. And I hope it can introduce its spunk once again. W7, by far, is my favorite operating system aside from CentOS. :)

    2. About UAC, btw, I don’t think it’s necessarily stopping much, because it still gives the end user the choice to run applications. Half of viruses isn’t enough, sincerely. Without UAC, most computers can run well with an anti-virus solution. However, I’ve created small pieces of experimental malware that have passed:

      1: UAC
      2: Microsoft Security Essentials
      3: NOD32
      4: Avast!
      5: McAfee

      I haven’t tested others, but I felt it’s enough of a proof-of-concept that computers are safest when the user uses common sense and tools like Virus Total. But yes, however minimal, UAC does put something on the table in W7, as opposed to Vista.

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