The biggest Microsoft failures ever


One of the largest multinationals ever, Microsoft is known all over the world, thanks in large part to the huge success of its Windows operating system that greets millions of PC users every morning.

Founded in 1975 by Bill Gates and Paul Allen, the company has had its ups and downs through the years, but with a profit to date of over 18 billion, you’d have to say that there have been slightly more ups. Windows, Office, Xbox and, more recently Office 365 and its Azure cloud platform have been huge success stories. 

As with any success story (which isn’t yours), it’s often more fun to look at all the moments it hasn’t all gone to plan. So let’s all try to bolster our lagging self-esteem, and forget our own inadequacies for a few minutes, as we look at Microsoft’s biggest failures.

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Windows Vista

OK, time for a bit of a classic fail. You know it. It’s everyone’s least favourite OS of the naughties – Vista. Windows XP had been hugely successful since its 2001 launch but we’d waited a long time for the successor operating system. And Microsoft seemed to be having some problems with it. 

Released onto the masses in January 2007, Microsoft hoped Vista would be a hit as it aimed to be a highly secure, and speedy OS. As it turned out, it didn’t appear to be any more secure than previous OSes, and it also suffered from compatibility and performance issues – older PCs struggled under its graphical demands – making Vista slow and unwieldy.

Uptake was subsequently slow, and those who did take the plunge were thanked with crashes and general instability from the OS. Even with the Service Pack updates, which made things a little more bearable, Vista never managed to shift the egg from its face. A pretty poor show all round. Thankfully Windows 7 saw a return to form. 

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Microsoft Kin

The flop of the Microsoft Kin, although perhaps not a huge surprise, was quite a kick in the teeth for the Redmond-based giant. Its sales ended rather abruptly with the handset being taken off the shelves after just 3 months (from May to July 2010). The Kin didn’t even make it to Europe.

This decision to axe quite so quickly could have been down to Microsoft wanting to concentrate on the then imminent Windows Phone 7, but this theory is being kind to a handset that clearly did not appeal to its target market – hip teens and twenty-somethings.

It’s not altogether clear what caused the failure of the Kin, but a mixture of delays due to prevarication over the OS used, and subsequent lack of the important budget pricing by the agreed carrier, meant that this wasn’t one of Microsoft’s finest hours.

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BOB 1.0 (Yes, that was the only version)

No, BOB didn’t fail due to its really bad name – although it probably helped (a good, solid name if you’re a homo sapiens, but not so great for a piece of software). No, the name was a symptom of a wider issue – a poor concept executed poorly.

Released in 1995, the BOB user interface aimed to offer a non-technical option for those new to the whole computing thing.

The clever folk at Microsoft made a mistake a lot of clever people make, which is to think that everyone else is stupid; the only possible explanation for the development of this condescending/patronising UI. Yes, people at the time wanted something easy to use and effective – that’s nothing new – however, BOB was better suited to infant school children rather than adults.

It never got updated from version 1.0. BOB, no-one likes you and wherever you are, stay there and don’t come back.

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Windows Phone (and buying Nokia’s phone business)

Windows Mobile was the OS which Microsoft shoe-horned in from the early Pocket PC device to fit with smartphones. It wasn’t very good. But then Microsoft did something unthinkable – it designed a properly good mobile OS, called Windows Phone. It was still based on Windows Mobile, but it had the still-great tiled interface you can see above. 

Trouble is that when Microsoft announced Windows Phone 7, Android and the iPhone had already taken hold – it was several years too late. Few phone makers wanted to pay Microsoft for the software while Android was funded by increased eyeballs on Google sites and services. Because others failed to take up Windows Phone, Microsoft bought Nokia’s phone division to make its own smartphones. This was also a total failure. It had to write down a loss on the acquisition of $7.6 billion. 

There was a Windows 10 Mobile version of Windows Phone in 2015, but it wasn’t until 2017 that Microsoft finally started recommending that people use Android or iOS instead. 

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Zune Player

The Zune player is a bit of a strange one, as it was a pretty competent all-round media player for a time when we didn’t stream everything on our phones. However, Microsoft completely failed to capitalise, resulting in poor sales.

Launched in late 2006, Microsoft clearly had hopes that it would be a competitor to the iPod; research group NPD stated in 2009 that it had a depressing 2 percent share of the media player market – very much in the shadow of the iPod’s 70 per cent.

Zune never had a UK launch – indeed, it was never made officially available outside of North America. 

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Office Assistant (Clippy)

The Office Assistant was part of Microsoft Office versions 97 to 2003, and after poor feedback Microsoft turned the default to off. And it was taken out completely by the time Office 2007 came along.

The failure of this feature in Microsoft Office was possibly not so much down to the fact it was entirely unhelpful, as we’re sure it could well have guided a few people through tasks not yet known. However, the one thing you can’t deny is that Clippy as he was dubbed, was bloody annoying.

It is possible that Clippy has been blamed for more causes of office rage than any other contributing factor, and subsequently, Clippit is a failure for the simple reason that nobody likes being told what to do by a paperclip – especially a smarmy virtual one.

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