Microsoft’s Greatest Failures

Behind every successful company there’s always a few mishaps it would rather everyone forgot. Microsoft, despite being the top name in desktop computing, isn’t immune to the laws of failure, so we thought we’d have a look at a collection of some of the Redmond company’s greatest failures.

To be fair to Microsoft, you could easily apply the old adage of breaking eggs to make an omelette. The company has of course made some significant moves in the past, pushing the model of desktop operating systems from simple, flat windows to the fine specimen that is Windows 10; and let’s face it, Windows 10 isn’t too bad.

The company has, along the way, come up with a few stinkers, but to get to the rock solid OS that is Windows 10 the designers, developers and software experts, have pushed the envelope and tried new elements. These new elements haven’t always worked, but at least they’ve tried. The same can be said for other departments within the company. However, that doesn’t stop us from having a giggle at some of the flops Microsoft has produced.

Windows ME

Let’s begin by addressing the elephant in the room: Windows ME. Released in 2000, this is an operating system that Microsoft would really like to brush under the rug, and wipe everyone’s memory of such a thing ever happening. It was terrible. Oh boy, was it terrible.

Windows ME, Millennium Edition – or Mistake Edition – started life on September 14th 2000, as a follow up and final 9x edition of Windows to the incredibly good Windows 98 SE. ME was supposed to be the one OS to finally bridge the gap between consumer editions of Windows and the business stability of the NT kernel. Unfortunately, things didn’t go quite to plan and the connecting project, which would have brought the NT code into the mainstream consumer systems, was eventually dumped. Interestingly, the code that was worked on would eventually be used once more in the Whistler project, which ultimately became Windows XP.

Windows ME, despite being rushed to the shelves, did promise a better overall system than the current consumer edition, Windows 98SE. Microsoft bragged about faster boot times, better support for the emerging USB devices, better support for scanners and printer, better support for online connectivity and collaboration as well as network technologies, improved power management, and far better media resources. What the users got though was something rather different.

Windows ME was plagued with problems from the moment you put the disc in the drive. The installation routine was buggy, the initial setup was buggy, the initial login was buggy. If you somehow managed to escape the Blue Screen of Death during the setup, then you would soon discover an operating system that crashed randomly, didn’t install the right drivers, and somehow managed to wipe and corrupt software that was installed on another drive.

After only a year of being made available, the plug was pulled on ME and quickly replaced by the immensely better Windows XP. Microsoft then did the digital equivalent of taking the failed OS out into the desert and introduced it to the business end of a loaded gun. To use a quote from the Urban Dictionary. “If someone IMs me, Windows ME crashes. If I open a webpage, Windows ME crashes. If the phone rings, Windows ME crashes. If a butterfly lands on a flower in the rainforest, Windows ME crashes.”

Windows Vista

Windows XP was a damned good operating system. Stable, quick, and perfect for gaming on. In the work place you could throw anything you want at it, and it took it on the chin. Its successor, however, wasn’t so good.

Windows Vista appeared on the scene early 2007, and it was sold as a bright, bold and very new approach to the tired and worn desktop model. ‘The wow starts now’ was the slogan Microsoft was bandying around before the official launch, and from what the consumers saw, it did look rather impressive.

Sadly, as soon as you got your copy of Vista home and inserted into the CD drive is when the problems started. Vista struggled on even a decent specified machine back in 2007, and in a world where most of us don’t own £1,500-plus computers, this meant that Vista didn’t really like being installed an anything other than a high-end performance box. Black screens, spinning mouse cursors, load times that would seriously take minutes, and elements of the desktop that refused to load, were the order of the day for most folks. As such, Vista became the rod in which to beat Microsoft.

It didn’t help that computer shops and retailers were running adverts claiming that their systems were ‘Vista-free!’, or ‘We’ll remove Vista for free!’. Soon enough, Vista was dumped in favour of Windows 7, where Microsoft reversed most of what it had done and returned to a more familiar design and setup.

Interestingly, Vista did pick up after you applied a few service packs and tweaks. But it was too little, too late for this dead-on-arrival OS.

Surface RT

Microsoft’s Surface tablets and laptops are, beyond the Xbox, one of the company’s most successful hardware lines. However, the name Surface didn’t always have the Midas touch for Microsoft.

The Surface RT was a hybrid tablet, and the first ever personal computer designed in-house by Microsoft. On paper it was a great concept, but it failed due a couple of major features that forced Microsoft to eventually go down a different route for its Surface line of technologies.

The first issue was that the Surface RT used an ARM processor, which although kept the costs down, did prove to be something of a developmental headache for the company. The second element, is the use of Windows RT, a much scaled down variation of Windows 8 that was developed for use on ARM architecture devices.

While there are many ARM-based devices in frequent use: phones, tablets, Raspberry Pi and so on, using one in a product from a company that also produces the world’s most used office productivity suite wasn’t such a good idea; especially considering there wasn’t really any good backward compatibility with Windows apps. This meant the Surface RT was somewhat limited, and customers felt that all they had was a trendy-looking paperweight.

Windows RT, now discontinued, was met with a lukewarm reception by many. Its performance was awful, its store was bleak, it wasn’t stable enough for other big companies to develop for, and such, it was quietly swept under the carpet.


Microsoft really dropped the ball when it came to mobile devices. The Surface RT, Kin, the Windows phone, and in particular, the Zune.

Launched in 2006, nearly five years after Apple had released its iPod, the Zune was much too little too late. In the eyes of the media, bad timing on the part of Microsoft, poor marketing, and a lack of motivation from the developers were to blame for the failure of the Zune. Low quality, and a sparse library of music were what most of us thought of the Zune within a few weeks of its release.

With Apple the king of the MP3 market, the Zune didn’t stand much of a chance. The company managed to drag out four generations of the product before finally sealing the coffin on the Zune in 2011, a mere five years after it was first released. A sad failure for Microsoft, and a costly one too, with the loss of an estimated $290 million.


An odd one, the Microsoft Kin, that was released in May 2010 and discontinued in July of the same year. Indeed, three months for a device that cost the company upward of $240 million and ate into the Xbox budget. If there was ever a poster child for a failure, then the Microsoft Kin would be it.

The Kin and its Kin OS, based on Windows CE, didn’t even make it over to Europe, and it didn’t go down too well with its target audience – who were already knee deep in iPhones and Android devices – at the cost of around $130 per clam-shaped device.

The Kin certainly wasn’t one of Microsoft’s finest hours.


Back in 1995 Microsoft made the mistake that a lot of big companies make: assuming everyone is stupid. Essentially, BOB was an interface designed to help novice computers users navigate and use their systems. With BOB were a number of companions, such as Rover, who provided speech bubbles to help you guide yourself around the OS.

BOB managed to get to version 1.0 before he/it was discontinued, and it’s not surprising either. With a UI that looked like something from an early LucasArts Point-and-click adventure, this ‘helper’ software was an enormous resource drain and was frequently criticised for patronising the user instead of actually helping them.

Yep, although a nice idea, BOB was an embarrassing failure for Microsoft.

Windows Phone

Based on Microsoft’s previous mobile device fails, you would have thought the company would finally get the hint and leave the mobile market to the likes of Android and Apple. But no, instead it launched the Windows Phone.

Released in 2010, the Windows Phone and its OS, Windows Phone 8.1, didn’t fare too well. The device did manage a five year lifespan from first to final releases, but at an estimated cost to the company of over $7.6 billion – which also included the purchase of the Nokia assets – the Windows Phone is by far the most expensive failure the company has ever developed.

Windows Phones just didn’t hit the mark with the mobile community. While they looked decent enough, and in some instances they worked perfectly well, it was simply too late for Microsoft to join in with the other names. The take up on Windows Phone was poor, to the point where many mobile stores were offering a free Xbox with every Windows Phone purchase.

To the future

For every Windows ME there’s a Windows 7, and although Microsoft has had its share of poor judgement calls in the past, the company does seem to have reigned in most of its odd-ball projects; concentrating on Xbox and Windows 10 development mainly, together with the successful Surface brand. Thankfully, its server models are fairly strong, so despite the billions lost in failures, it still has enough in the coffers for a few more decent additions to the family.

But time will tell. Who know, we could add a few more in the next ten years.

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David Hayward

David has spent most of his life tinkering with technology, from the ZX Spectrum, getting his hands on a Fujitsu VPP5000/100 supercomputer, and coding on an overheating Raspberry Pi. He's written for the likes of Micro Mart, Den of Geek, and countless retro sites and publications, covering reviews, creating code and bench testing the latest tech. He also has a huge collection of cables.

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