Simultaneously one of the most successful and reviled technology companies in the world, Microsoft has had a lot of ups and downs over its 40 year history, to say the least. Known primarily for their Windows operating systems, which remains the dominant OS of the world’s computers, Microsoft has dabbled in everything from software to video games to mobile phones. The company is currently in the middle of a brand resurgence thanks to restructuring efforts under the leadership of CEO Satya Nadella and is poised to release the hotly-anticipated Windows 10 later this year. Every new tech release is a gamble, but it’s unlikely that Windows 10 will find itself in the same company as these 10 infamous blunders.

10. Windows 8

Credit where credit’s due: Windows 8, released in 2012, is actually a solid operating system with a number of technical improvements over Windows 7, including better performance and enhanced security features. The problem is that all of these good components are hidden under a confusing and inefficient user interface. Windows 8 utilizes a tile interface designed to mimic the experience of touch devices like smartphones and tablets. While this sort of UI works well for small screen touch devices, it doesn’t translate well to the personal computer market. Windows 8 was too different from previous Windows products, prompting Microsoft to release a number of improvements with its 8.1 update that restored some classic Windows functionality. Although Windows 8 was a sales success, its follow-up, Windows 10, is set to arrive sans-tiles later this year.

9. Blue Screen Presentation

Microsoft has had its share of hilariously ironic snafus over the years, but the infamous blue screen of death that sabotaged Windows ’98 live demo sits comfortably at the top of the list. The poor presenter’s “whoa”  is a perfect example of a man poking fun at the sheer terror he’s surely feeling (it doesn’t help that his boss is on stage with him). The best part though has to be Bill Gates trying to save face by quipping that, “this must be why Windows ’98 isn’t shipping yet.” Yes, there’s nothing quite like having your product fail on live TV to assuage any doubts about its reliability.


8. Tablet PC

Microsoft has been having lots of success in the tablet market with its sophisticated Surface Pro, but things didn’t start out so well for the software juggernaut when they introduced the Tablet PC back in 2001. The problem with this early model is that it didn’t play to the strengths of the tablet market, as it was too similar to traditional desktops to make it a worthwhile investment for most consumers. It also didn’t help that the price was supremely high, going for $2000 and up in most cases. This was definitely a case of Microsoft putting the cart before the horse, so to speak.

7. The Xbox One Annoucement

Microsoft’s Xbox division has been largely successful since it first entered the home game console market in 2001. After two hardware generations of knowledge-building and learning lessons, you would think Microsoft would have known the right moves to make when it came to announcing its third console, the Xbox One, in May 2013. You’d be wrong. The whole conference was a PR disaster, as each new feature (always-online requirements, forced Kinect integration, elimination of used games) was met with disdain from the tech community. Thankfully for everyone, Microsoft soon took the hint and eliminated most of the unpopular features from its new console, but their initial blunder translated into weaker-than-expected sales for most of the console’s first year on the market.

6. Clippy The Office Assistant

When Microsoft Office 97 was released, it came with an on-board assistant called Clippy, an anthropomorphic paper clip designed to provide helpful hints to the user. Unfortunately, Clippy turned out be more annoying than helpful, popping up incessantly to provide assistance that was largely unneeded. Thanks to criticism from consumers and even Microsoft’s own employees, Clippy was put out to pasture in 2001 and eliminated as an Office feature altogether in 2007.  Fortunately for Clippy fans (there have to be some, right?), the infamous paper clip was featured as a running-gag in Microsoft’s interactive tutorial for Office 2010, the appropriately titled Ribbon Hero 2: Clippy’s Second Chance.

5. Games For Windows Live

Xbox Live is generally considered a prime example of how to do a game networking system right, which makes it all the more baffling that Microsoft largely blew it when it came to offering a similar experience for PC games. Game for Windows Live was an initiative started in 2007 that offered features like cross game friendlists, matchmaking, and achievements. The problem was that, rather than improving and streamlining the user experience, GFWL ended up being more of a hindrance than anything, with stuff like installation issues, corrupted save files, and regional restrictions making the initiative very unpopular with players. Thankfully, the domination of Valve’s Steam service and Microsoft’s own methods of sabotage (Xbox Live, not Windows Live, was integrated into Windows 8 — confusing? You bet!) largely eroded this failed online service’s impact, with speculation that it’s only a matter of time before Microsoft shuts it down completely.

4. Internet Explorer 6

The entire Internet Explorer brand has the unenviable reputation of being the worst internet browser available and most of that hate can be attributed to the blunders of IE6. Released in 2001, IE6 was so full of security issues it prompted PC World to claim, “[it] might be the least secure software on the planet.” Microsoft was also famously complacent about contributing significant updates and improvements to the software, as they had such a dominant hold on the browser market at the time. Unfortunately for Microsoft, this complacently allowed better browsers like Mozilla’s Firefox and Google Chrome to gain market share, with Explorer going from around 90% in the mid-2000s to 28% in 2015.

3. The Zune

There’s a reason Apple’s iPod became synonomous with portable mp3 players and Microsoft’s Zune did not: sales. The iPod has lifetime sales of around 385 million (and the iPhone has almost doubled that at 726 million). Exact sales figures for the Zune are difficult to come by, but the device only had about a 2% market share before it was discontinued in 2011. Unlike most blunders though, the Zune’s failure didn’t come down to its quality, as it was actually a very capable media device. Some critics have even made the claim that the Zune, despite being a flop, actually helped Microsoft recover from an innovation tailspin, which would explain the company’s resurgence over the last half decade.

2. Microsoft Kin Mobile Phone

If you’ve never heard of Microsoft’s Kin line of mobile phones, you’re probably in the majority, as the brand was extremely short-lived with only 2 months on the market in 2010. The main problem with the Kin is that it existed in a weird liminal space — too underpowered to be considered a full smartphone, but too capable to fit into the traditional mobile market either. Microsoft wound up learning from the mistakes of the Kin in its much better realized Windows phone line, which haven’t exactly been a sales marvel, but are still worthy alternatives to iPhone and Android devices.

1. Windows Vista

Microsoft is synonomous with its Windows operating systems and there have been some notable ups and downs over the brand’s decades-long hold on the computer market. Vista, the successor to the popular, well-liked Windows XP, represents the biggest misstep the Windows brand has ever had. Vista was released in early 2007 and quickly garnered widespread critical disdain thanks to issues such as its high price, demanding system requirements, and lack of compatibility with various software and drivers. Vista also suffered from a lack of support from IT departements who saw no real reason to eliminate the reliable XP from businesses. Vista was so bad that a follow-up, Windows 7, was released less than 3 years later in order to address all of Vista’s issues.