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Top 10 worst Microsoft products of all time

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31 Oct 2009, Shaun Nichols  , V3

Last week, in honour of the Windows 7 launch, we covered Microsoft's biggest successes in the computing field. This week, in the interest of balance, we're looking to the company's dark side.

Every company has its hits and misses. Microsoft, however, seems to have a tendency to miss a lot more often than other companies. Perhaps it's because the company has been so big for so long, or perhaps it's because people are always so eager to point out the faults of the Redmond giant. But no matter what the reason, Microsoft's list of flops is long and legendary.

So this week, we count down 10 of what we think are Microsoft's biggest duds. It's been a tough one to write, not because of a shortage of candidates, but because we had to hold ourselves in check. We've suffered through all of these examples and the temptation to rant has had to be curtailed. We've managed to keep it under 5,000 words - just - but if time had permitted we could have doubled that.

EncartaHonourable mention: Encarta
Iain Thomson: In under 24 hours Encarta will be no more, except for the Japanese version which gets a stay of execution. So let's dance on its grave a little.

Encarta was one of those 'seemed like a good idea at the time' things. I suspect more than a few Microsoft staffers grew up with a full set of the Encyclopaedia Britannica and loved them dearly. I'd also suggest that someone looked at the thousands of dollars that the Britannica crew were charging, and figured they could get a slice of that pie.

The result was Encarta, and it was about as much a threat to Britannia as Bambi to Godzilla. Encarta was clunky, badly written and had more than a few inaccuracies. It was also a sizeable bit of software and was pricey for what it was.

But what really killed Encarta was Wikipedia and the power of crowds. Wikipedia beat off a host of researchers and software engineers because nothing commercial can overcome people doing something for fun.

Shaun Nichols: It's a bit ironic how Microsoft, a company known for wiping out countless numbers of competing products from smaller vendors, is now being forced out of this market by a project created almost exclusively by small and independent groups. Wikipedia may have its faults, but you have to applaud it: if nothing else, it has got rid of Encarta.

Still, it seems that Britannica can't be too far behind. Unfortunately the encyclopaedia vendors took far too long to move from the CD-ROM to online services, and as a result users stepped in and created Wikipedia. It's a bit of a shame, because Wikipedia is flawed, and multimedia encyclopaedias did have uses in a number of areas.

Hopefully, somewhere down the line, somebody will relaunch another encyclopaedia service to keep Wikipedia on its toes. We shall wait and see.

Ms-deweyHonourable mention: Ms Dewey
Shaun Nichols: A few years back, Microsoft was looking for a way to boost interest in its MSN Search service. One of the ideas was an interactive search site dubbed Ms Dewey. The live-action search allowed users to submit queries which would be answered by a wise-cracking actress.

Unfortunately, the idea of a pretty lady who would answer all your questions caused almost everyone who used the site to revert to the intelligence level of a 14 year-old boy, and most of the time on the site was spent asking dirty questions. Things only got worse when some of the steamier early work by Janina Gavankar, the actress who played Ms Dewey, began to surface.

The site didn't last very long, as Microsoft could not have been thrilled by the reception it got. The company had hoped to create a cute little marketing gimmick that would bring more attention to its search service. Instead, the campaign ended up looking at best amateurish and at worst a bit sleazy.

Iain Thomson: Actually Shaun, I think there's more than a little of the teenaged boy in many people in the technology field. Look at previous female personifications brought to life on the computer: they are all failures and seem to have come from the bottom of a teenager's sock drawer.

You can't condemn Ms Gavankar for some of the schlock she's done early in her career; we've all done things we aren't proud of (see number five of this list for example). I thought she did the job rather well. The problem is that the job itself was a duff one.

Apparently the Ms Dewey search idea wasn't Microsoft's but came from its advertising agency. I can believe it. The whole concept seems perfectly suited to people who know very little about computers and their users, and was probably inspired by a liquid lunch and a generous helping of Columbian marching powder.

Dos10. MS-DOS 4.0
Shaun Nichols: In last week's Top 10, we named DOS 5 as one of the 10 best releases from Microsoft. It was a nice example of just how good DOS could be when done right.

This week, we take a look at just how bad DOS can be when it's done wrong. DOS 4 was released in 1988 and soon became known as one of the all-time worst versions of the operating system.

DOS 4 was riddled with bugs, and in many cases, applications could not run on the product. As Windows was still in its infancy, many users still made heavy use of DOS and this was a pretty big problem. In 1989 Microsoft rolled out the 4.01 update, thus providing an early case for the concept of waiting a year on any Microsoft software update.

Iain Thomson: DOS 4 was so awful it nearly got me to by an Apple – yes, it was that bad. I think Microsoft was just trying to do too many things at once. It was still locked in a battle with Digital Research for control of the DOS market, but was also getting into bed with IBM to develop OS/2, albeit half-heartedly.

Microsoft even ran ads saying DOS was dead after version 4 but, based on the operating system's performance, there were many users willing to bury the thing.

It was phenomenally buggy, and crashed more often than a blind stock-car racer. I think I spent more time in the late 1980s watching the computer boot up and then freeze than doing anything useful on it. Our university IT department eventually caved in and reverted to DOS 3.

To make matters worse Microsoft didn't fix the most obvious problems for a year. It's no wonder so many people left their PCs in the bin and went over to Apple.

Ie5-logo9. Internet Explorer 5
Iain Thomson: There was some intense discussion about what version of Internet Explorer we were going to include. I was tempted by IE6, since it hung around like a bad smell for five years while Microsoft gallivanted off doing other things.

But instead, we opted for IE5 for the part it played in Microsoft's history. IE5 was pivotal in Microsoft's plans to tie the browser so tightly into the operating system that it would give the company the whip hand and ensure that if you used Microsoft you also used IE.

It was a shameful piece of anti-competitive practice, and one that is only now being sorted out to the satisfaction of some regulatory bodies. No-one knows which bright spark at Redmond decided on the strategy, but in my opinion this looks like a Ballmer move; he's always been a little too aggressive when it comes to business strategy.

The courts examined this case very closely. At first Microsoft said that IE5 couldn't be removed since it was an integral part of the operating system. The prosecution then wheeled out a version of Windows that did just fine without it. Eventually the US courts decided that Microsoft had done wrong and the company narrowly missed getting broken in two.

Shaun Nichols: The problem with IE5 wasn't just that it was a bad product, but that it was a bad product which a great many people were stuck with. Firefox had yet to truly emerge, and Opera was toiling in anonymity. For most of the users out there, it was IE or nothing.

Fully aware of this, Microsoft went ahead and did little to nothing. It wasn't until Firefox started knocking on the door that the company really got off its butt and significantly improved the browser. And it wasn't just users who suffered. As Iain noted, IE5 was bundled with Windows as a free component.

Seeing as how much of the internet was just coming of age around that time, Microsoft gave itself an unfair advantage that wiped Netscape out once and for all, but also kicked off the landmark anti-trust case that hounds Microsoft to this day.

Windows95-desktop8. Windows 95
Shaun Nichols: Windows 95 was supposed to be the killer operating system for the PC platform. As the emergence of the internet and sophistication of the home computer was bringing many first-time buyers into the market, Microsoft took aim at this growing user base by promising a sleek, easy-to-use operating system. What they got instead was a textbook example of why people loved to hate Microsoft in the 1990s.

Touted as a major leap in computing prior to its release, Microsoft spent hundreds of millions of dollars to promote the system, using publicity stunts such as projecting the Windows 95 logo onto the Empire State Building.

Unfortunately, Windows 95 wasn't as revolutionary as some had hoped. Emerging hardware standards such USB, AGP and Intel's P6 architecture had little or no support in early versions of Windows 95, and it wasn't until 1997 that all of the kinks were ironed out.

Of course, not long after that Windows 98 came along and replaced Windows 95 anyway.

Iain Thomson: The launch of Windows 95 was a huge deal and the biggest marketing campaign in Microsoft's history. However, one man was distinctly unimpressed: Douglas Adams.

Among all the hoopla, Adams wrote a brilliantly savage takedown of the operating system and hit the nail on the head. Windows 95 did what Apple had done for years, and did it worse. That didn't stop him selling software for the system but it was a welcome note of logic.

Windows 95 just wasn't that good. The GUI was clunky and you needed top-of-the-range kit to run it at a speed approaching usefulness. But that didn't matter to most customers because it finally made the PC as easy to use as an Apple.

Shaun has it right to an extent, in that Windows 98 was the operating system Windows 95 should have been. But this ignores the fact that, by the second edition of Windows 95, it got a lot better, and lasted on some corporate systems for years.

Zune7. Zune
Iain Thomson: Apple's iPod basically created the mass market media player industry. It had cool players and the software to back it up. So naturally, Microsoft wanted to get in the game and suck up some of that lovely revenue.

However, Microsoft seems to have missed one of the essential laws of the technology industry. Many companies have their cool moments. Apple is probably the most commonly called cool, but Sony, Nokia, Cray and even IBM have had their stylish moments. But Microsoft is not, and never will be, cool. It's the IT equivalent of your dad's fashion sense; elasticated trousers are very sensible but they'll never grace a Milanese runway.

That aside, the Zune was also an awful bit of kit. It was tied to Windows, for a start. Maybe Redmond decided that no Apple user would abandon their iPods, but making it impossible for them to do so was just plain stupid.

Then there were the other features. The FM radio was a nice idea, but it had a tendency to drain the battery on early models. Wi-Fi was an excellent addition that could have won over more than a few iPod users if only Microsoft hadn't crippled it.

Then, to add insult to injury, the device was limited to the US market. It was a year after launch that the company started sales in Europe. If someone had visited the US, bought one of the devices and then bought it back to Europe, they'd find the company putting blocks in their way to using it. Truly, the device from hell.

Shaun Nichols: I've always said that the Zune didn't fail because it was a bad product, but because it wasn't a superior product. There were gripes about the Zune, but then there were also some strong points.

In reality, when the Zune and iPod were stacked side by side, the Zune didn't wither away in comparison. Unfortunately for Microsoft, 'comparable' just didn't cut it. The iPod was at the height of its popularity, and users were in love with the combination of iPod and iTunes.

Simply put, there was no 'killer app' that gave anyone a reason to dump the iPod. Internet Explorer had the tie-in to Windows. The Xbox had a pack of highly-popular exclusive games and online play. The Zune had none of these, and users really had no appreciable reason to switch over.

Microsoft-bob6. Bob
Shaun Nichols: Few products are more synonymous with Microsoft's shortcomings than Bob, the ill-fated navigation system that was bundled with Windows 3.1 and 95.

At first glance I wanted to put it much higher on this list, but Iain had some very compelling reasons to move it down, the first being that he can fire me and the second being that Bob was hardly a mission-critical component. Faced with this excellent reasoning, I conceded and we placed Bob in sixth.

The concept behind Bob was to provide an easy-to-use interface for beginners and first-time PC buyers. With memories of command-line systems such as Unix and DOS in the mind of most casual users, Microsoft figured that a simplified interface would help sell more machines. As is often the case with Microsoft, however, a good idea didn't translate into a good product.

Bob came off as a bit of a boob, so to speak. The application required relatively high hardware features for the day, meaning that the low-end machines of many first-time buyers couldn't run it. On top of that, Bob was a bit too simple, and after a short time even the most inexperienced user wanted to turn it off and actually use the rest of their system.

For anyone who had spent any significant amount of time with a PC, Bob was seen as little more than a children's toy, and having friends see you using it was akin to riding a bike with training wheels.

Not long after its release, Bob was discontinued and Microsoft wisely did what it could to erase him from the collective memory of the computing world.

Iain Thomson: Oh come on Shaun, you know your job doesn't depend on the list, it depends on your arguments and the ability to take a punch to the jaw. But, while Bob was a monstrous screw up, there were more deserving cases to go higher on the list.

Bob is legendary in computing circles for being so hideously bad that it has been almost airbrushed out of Microsoft's history. It had an interface that a child would love but the average consumer hated. You can't take a system seriously when it's got sections run by Chaos the Cat and Scuzz the Rat.

On one level, however, Bob was a major success. The future Mrs Gates was on the team that created Bob, so I'm sure Bill remembers it with fondness.

Activexcontrolvb5. ActiveX
Iain Thomson: OK, confession time. About 15 years ago I left journalism and its triumph of salary miniaturisation and went into public relations. One of my jobs was to launch ActiveX into the UK market with a straight face. Needless to say, it wasn't long before went back to journalism.

ActiveX makes the list because it was poorly thought out and Microsoft was so slow to fix many of the problems. In some ways ActiveX is blamed unfairly for many of the flaws in IE. But it did fall down in some important ways.

Primarily ActiveX was very easy for adware companies and malware writers to subvert. Yes, that was down to those companies but Microsoft provided the framework and assumed that users were savvy enough to spot a bad ActiveX control. They couldn't, and the results were horribly bad for many users.

Having these problems was bad enough, but Microsoft's attitude ranged from sticking its fingers in its ears and shouting 'La, la, la we can't hear you', to the kind of grudging fixes that infuriated users and delighted those trying to subvert Windows.

Shaun Nichols: As with a great many things, ActiveX was a good enough idea that had a highly unpleasant side effect. The ability to integrate third-party applications with the web browser was a pretty neat idea, unfortunately it also opened a Pandora's box of security issues. Sort of like a weight loss pill that causes you to turn orange and grow a third arm out of your chest.

You see, by adding components to open third-party applications from the browser Microsoft allowed web pages to access those applications through the browser, and access to all of the security vulnerabilities within the browser.

Suddenly, malware writers could not only exploit vulnerabilities in the browser itself, but they could use ActiveX plug-ins to access and exploit the vulnerabilities in other applications, such as Word and Excel. If you do get your system compromised through Internet Explorer these days, there's a fairly good chance that you have an ActiveX plug-in to thank.

Vista4. Windows Vista
Shaun Nichols: Vista itself doesn't get placed higher on the list because its failures weren't entirely the fault of the operating system itself.

Vista really did contain some cool new features and important security improvements over Windows XP. Unfortunately, they weren't nearly enough to justify the amount of time, money or hype given to the release.

The other problem was that Vista had big shoes to fill, and Microsoft simply did not deliver. As with other Windows updates, Vista had its share of bugs and compatibility issues. Not too bad in the grand scheme of things, but a major gaffe when you consider that Microsoft had spent years hyping Vista and had promised that it would be the biggest thing since Windows 95.

Vista was supposed to be the most important Windows update in more than a decade. As it turned out, the update was so bad that many people refused to install it, opting instead to stay with the ageing Windows XP.

Iain Thomson: It was Microsoft that doomed Vista before it was even released. The company spent so many years telling us how good it was going to be that the actual product was an understandable anticlimax.

Vista was originally promised for 2003/4 and kept on getting pushed further and further back. Now, in the past Microsoft has pre-announced software to stifle competition, such as in the days when it was fighting for the DOS market with Digital Research. But with Vista there was no such need.

Microsoft also mucked up by announcing all the great new features Vista would have, and then dropping them as deadlines slipped and the market grew more and more impatient. It was a recipe for disaster.

As for the launch itself problems began to emerge quickly. Driver support wasn't there, the multitude of options was confusing and it needed a huge amount of hardware support. I'd no more consider running Vista with less than 2GB of RAM than I would turn up at a press conference without a notebook and a cynical attitude.

Nevertheless, I think we're seeing a Windows 95 situation here. After the service packs, Vista wasn't as bad as it had been. But it's a measure of how deep a hole Microsoft recognised it was in that it got Windows 7 out so quickly.

Windowsvistacapable3. Vista Capable
Iain Thomson: Microsoft was very late getting Vista to market, years late as it turned out. But when it finally was due, Microsoft realised it was going to miss the all important last quarter of the year.

Lots of PCs get bought in the run up to Christmas, and Vista wasn't due until January 2007. This understandably made a lot of hardware vendors very unhappy, since it was clear that consumers weren't going to buy a computer if they had to buy a new operating system a few months later. So some bright spark came up with the Vista Capable and Vista Ready campaigns.

If your computer was labelled Vista Ready then customers knew it would run Vista easily, and Vista Capable would also be able to run the software, if not as well. To seal the deal, buyers got a voucher for a free or reduced-cost upgrade to Vista once the operating system was out. Job done, and one analyst reckoned the company saved over $1bn with the campaign.

However, this cunning plan was fatally flawed. Vista demanded a lot of hardware to run and some Vista Capable machines could run only the most basic version of the new operating system, and even then at the speed of a drunken snail. Naturally, people were upset and some folks sued. The result was the public opening up of a slew of emails that proved highly embarrassing to Microsoft.

It seems some senior Microsoft staff knew from the start that some of the machines being sold as ready for Vista were nothing of the sort. In addition some hardware vendors were furious that Microsoft had downgraded the hardware needed to be Vista Capable to please Intel.

The courts are still ruling on this one, so we'll see how it turns out. But it was hardly Microsoft's finest hour.

Shaun Nichols: We actually decided to separate Vista and Vista Capable on this list, because we felt that each of the screw-ups deserves to be recognised on their own merits. And I would argue that the roll-out of Vista was a far bigger disaster than the operating system itself.

Perhaps the biggest gripe about Windows Vista was the 'Vista Capable' criteria. The company figured that it could help users avoid many of the headaches that had been associated with previous versions of Windows and offer a simple 'yes or no' label.

The only problem was that, well, Microsoft couldn't give a simple 'yes or no' answer on Windows Vista because there were so many different vendors building PC hardware and several different versions of Windows Vista with varying hardware requirements.

To make matters worse, there are now parties who suggest that Microsoft was not only misguided with the programme, but downright deceptive. It's bad enough that Microsoft is having to pump up Windows 7 as the operating system that Vista should have been, but it will only get worse if the company is found to have lied to customers on top of that.

Clippy-letter2. Clippy
Shaun Nichols: Bob was regarded as one of the more amusing failures in Microsoft's history. An early attempt to simplify computer use, Bob was instead received as an annoying gimmick that drove people crazy.

You would think that after such a fiasco Microsoft would learn its lesson, but no. With the bitter taste of Bob still lingering, Microsoft set out to create an even more useless, intrusive and irritating piece of idiotware: Clippy. The infamous animated paper-clip shipped with Microsoft Office 97-2003 had a six-year run which tortured users and gave office supplies everywhere a bad name.

Think of the annoying salesperson who pops up behind you and repeatedly asks if you're finding everything OK, or the guy who stands over your shoulder while you're fixing something in the garage and offers unwanted advice. Clippy was like both of those people, combined with an irritating children's cartoon character. Obviously, when you're on a deadline and rushing to finish a business report or term paper, nothing is more helpful than an annoying cartoon paper clip popping up on the screen and offering to help you write up your grocery list.

Thankfully Clippy was killed off in the most recent versions of Office. Hopefully Microsoft has finally learned its lesson and we won't have to deal with an even more annoying animated utility in the future, but I'm not optimistic.

Iain Thomson: Microsoft has never released the name of the person who came up the idea for Clippy, and for good reason. Several million computer users would be after them with murder in their hearts and police wouldn't have to look far for a motive.

I swear IT administrators got more calls about Clippy that any other piece of Microsoft kit. The overwhelming question was how to turn it off before people snapped and took a chainsaw to their PCs. It was a nadir in stupid software.

You have to wonder what Microsoft was thinking. Maybe there were some science fiction fans at the company who liked the idea of a computer helper. But Clippy wasn't a HAL or other advanced AI system. It was AD – artificial dumbness. It's still a running joke in the industry and I hope it remains so; that way no company will be so stupid as to do it again.

Windowsme1. Windows Me
Iain Thomson: When we decided to do this list I was dreading the argument with Shaun. I know he hates Vista and would want it for the top spot, but I felt we'd be not just flogging a dead horse but jumping up and down on the tins of dog food it had become.

As it turns out, he wasn't keen to have Vista on the top spot either and we quickly agreed on the winner, if that's the word. Windows Millennium Edition (Me) was an absolute dog of an operating system and even now is mocked as Microsoft's lowest point in operating system design.

To start off with the operating system was, in my opinion, the most crash-prone piece of software I've ever had the misfortune to run. It was as unstable as a Hollywood starlet with substance abuse issues, and many users got used to saving everything every five minutes just in case. IT administrators hated it for this reason and point-blank refused to roll it out in more than a few instances.

Then there were the compatibility issues. To speed up the boot time Microsoft limited access to DOS, but this also made some popular applications incompatible with the operating system. The system restore feature was a nice idea, but most users assumed that documents would also be restored, which wasn't the case, and occasionally even found the system restored deleted malware.

There was a widespread view that Me was a cash-in product, something Microsoft had stuck out there early to wring a bit more cash out of the Windows 9x line before moving over to XP. That may or may not be true, but it was certainly not a polished product and did wonders for sales of Apple's iMac.

Shaun Nichols: When users restored their systems with Windows 98, the software would occasionally also reinstall malware which had previously been deleted. Amazingly, the fact that it would deliberately reinfect your computer was not the worst thing people remember about Windows Me. That should tell you all you need to know right there.

Windows Me was one of those releases that Microsoft really should never have let off campus. After the first few tests, which no doubt showed that the system was incredibly error-prone, someone in the higher ranks of the company should have pressed the panic button and sent everyone back to the drawing board. It's hard to imagine a Steve Jobs or a Larry Ellison letting a dog of this calibre ship as a final release.

Last week Iain suggested that every other version of DOS was poorly built and worth skipping. I would suggest that the same holds true for Windows: 3.11 was a landmark release, Windows 95 not so great, Windows 98 much better, Windows Me was notably terrible, Windows XP very good, and Vista a train wreck. The good news is that, if history is any indication, Windows 7 shouldn't be so bad.

Do you agree?

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