Top 10 Worst Microsoft Products Ever

Officially known as the “Office Assistant,” Clippy was an early attempt by Microsoft to introduce primitive AI suggestive technology into its office applications. Shown on screen as an animated paperclip, this assistant would provide suggestions or attempt to “help” you while you worked in Microsoft Office. Although the intent was admirable, Clippy quickly became far more annoying than helpful. Knowledgeable users would often be interrupted in the middle of their work to be asked if they needed help, when they clearly were fine on their own. With the release of Office 2007, Microsoft finally put Clippy back in a desk drawer, never to be seen again.

Thanks to the miracles of the internet, the ability to download pirated software has never been easier. As a result, companies like Microsoft have tried putting safeties in place to prevent such theft. Windows Genuine Advantage was a means of detecting illegal copies of Microsoft Windows running on a PC. Spun to customers as a way to ensure their PCs were fully licensed, the program backfired in a spectacular fashion. Anything from firewall software to a simple Windows update could trigger a false-positive, rendering the PC barely usable by most. Microsoft moved on from the original iteration of this tool after Windows 7.

Back in the 1990s, the internet was still relatively new to consumers. Given that most people’s center of entertainment was in front of a television, many thought that’s where the internet should belong as well. WebTV Networks created WebTV which allowed people to use the internet on their television. Microsoft bought the service and in 2001 rebranded it as MSN TV. As history has now shown us, the future of internet use was never going to be in front of a TV set. Despite the low price point, mass adoption was never achieved, and Microsoft finally shut the service down in 2013.

The success of fitness devices like the FitBit inspired many companies to follow suit with similar options. The Microsoft Band was a short-lived attempt at an advanced fitness device that was worn on your wrist. Compatible with iOS, Android, and Windows Phone OSes, it seemed like a natural extension of Microsoft’s technology. The first iteration sold out very quickly giving Microsoft hope that the product had a future. But with the release of Band 2, things slowly went off a cliff. Between the high price point, lack of features, and a plethora of well positioned competitors, the software company gave up on the product only two years after its initial release.

PC or Mac? Apple or Android? Coke or Pepsi? It seems the market will often steer towards two major brands which consumers then choose between. Windows Phone was an attempt by Microsoft to try and surpass their two biggest competitors. Through several iterations of the Windows Phone platform, Microsoft proved they couldn’t take a desktop OS and put it on a smartphone. With Windows 8 having been a colossal failure, copying that interface to their mobile platform didn’t help increase their adoption rates. Combine that with the sheer base of users Google had, even the acquisition of Nokia and their release of the Lumia line couldn’t help them reach the top of the market.

Long before the days of Microsoft Windows having a “Start Menu,” users really just saw a collection of icons and folders on a screen. Microsoft Bob was an early attempt to change that. Instead of icons, Bob presented an interactive living room of sorts. Scattered around the room were things like a rolodex, a clock, pen and paper, and even a calendar. Clicking on the various items would then launch a corresponding application. It also featured animated cartoon characters to help you, which eventually did inspire the aforementioned Clippy. As creative as it was, Bob’s hardware requirements and goofy interface doomed the product. The lights on the Bob’s room interface went dark less than a year after release.

It may have been the most popular browser at the time of its release, but that doesn’t necessarily mean it was a success. Released in 2001, Internet Explorer 6 at its peak had about 90% of the market share for web browsers, mainly due to being included with every version of Windows. That amount of users helped illuminate countless security flaws and inconsistent behavior that plagued the software. Repeatedly slammed by developers, IE6 was notorious for its incompatibilities with industry standards that more advanced browsers were already supporting. Numerous dangerous vulnerabilities in IE6’s security would sometimes take months to fix, leaving users exposed to would-be hackers. By 2008, support for IE6 across the web began to drop, signaling the end of an era.

What is the most infamous failed Microsoft operating system? Windows 8? Windows ME? Not quite. Of all the operating systems the company has released, Windows Vista would have to be considered the biggest failure on the OS side. Intended to be the well anticipated follow-up to the highly successful Windows XP, Vista never stood a chance in comparison to its elders. Plagued by a long and difficult development cycle, Vista received mixed at best reviews upon release. Some of the biggest criticisms lay around hardware requirements, the new UAC system, and countless other new “features.” Everyone was happier when Windows 7 finally replaced it in 2009.

Unless you’ve seen one on the “Guardians of the Galaxy” movies, it’s very likely you’ve never heard of the Microsoft Zune. Introduced in 2006, the Zune was meant to be a direct competitor with Apple’s iPod. Unfortunately, Apple’s stronghold on the portable music market pretty much doomed this from the beginning. It was a case of Microsoft trying to play catch up with a device that users didn’t want and an interface they weren’t interested in. Microsoft tried their hand again in the music space with Groove Music, but that came and went even quicker than the Zune did.

Never heard of the Microsoft Kin? Don’t feel bad. Nobody else has either. Released in the summer of 2010, this attempt at a social networking device originally lasted for 48 days. Portrayed as a messaging and social device, its integration with social networks was feature deprived, and didn’t come with any native instant messaging software. Adding insult to injury, there was no calendar to manage your social life, or contact list app to store your friend’s details. They revamped and relaunched it again in December of 2010 but even their new “n” line of Kin devices could make it through another year.

Have you ever used any of these Microsoft products? Give us the lowdown in the comments below.