Windows Vista

Microsoft introduced the widely hyped successor to Windows XP in January of 2007, and that was the high point for the OS. Consumers knocked it for its spotty driver support and intrusive security measures that interrupted even the most routine operations. Businesses, meanwhile, shunned Vista on concerns about incompatibility with older applications and horsepower requirements that were beyond the typical office PC. Microsoft hurried Windows 7 out the door in October 2009 in hopes the market would forget about Vista as quickly as possible.
BOB

Turns out most adults would rather learn to use a computer interface themselves rather than enlist the help of the childish, annoying, and at times condescending icons that were the hallmark of BOB-a Windows overlay that turned the desktop into a virtual house. Objects in the house were metaphors for common apps like word processors and spreadsheets, and goofy animations like Rover the dog helped the user find them. BOB debuted alongside Windows 95 and was shelved within two years (though Rover was reborn as Windows XP's canine search assistant).
SPOT Watch

The knock against a Microsoft-powered wristwatch-unveiled by Bill Gates at CES in 2003 -- was that only a computer geek would want one. And, uh, that turned out to be true. Despite Gates' prediction that Windows and spinoffs like Smart Personal Object Technology (SPOT) would ultimately provide the interface for a number of consumer products, from toasters to TVs, it remains mostly a desktop-bound OS.
KIN

Microsoft earlier this year sought to reach the social networking generation with the KIN One and KIN Two phones. The devices offered a unique interface that featured an always-on connection to sites like Facebook and Twitter. But critics knocked the KIN line for its expensive data plan and inability to run third-party apps. As one reviewer put it, KIN was just Windows Mobile with "a Susan Boyle makeover." Microsoft pulled the plug in early July after less than two months on the market as prices for the devices fell to one cent on Amazon.
Tablet PC

Call it the iBad. Microsoft launched Windows XP Tablet PC Edition in 2002 with an eye to gaining first mover's advantage in the slate market. But the platform proved premature. Shaky handwriting recognition, limited functionality, and expensive components made it a niche product at best for hardware partners like HP. Said Windows guru Paul Thurrott at the time of launch: "I strongly urge any potential customers to seriously consider how, when, and if they would ever actually use the tablet-based features of this product." Not many did.
UltimateTV

Microsoft hoped to be an early pioneer in the DVR market along with Tivo and ReplayTV, and anted up with UltimateTV in 2000. But the offering lacked Tivo's intuitive functionality while Microsoft also failed to score deals with major cable providers. Distribution was limited to DirecTV, a pact that died when EchoStar, with its own DVR technology, sought to acquire Microsoft's partner in 2002. UltimateTV vanished soon after.
Zune

Redmond's hardcoded software DNA appears to limit its chances of making a splash in the consumer device market. The best evidence is the Zune MP3 player. Despite years of investment and the recent opening of its own app store, Zune continues to be an afterthought in a market dominated by Apple's iPod. Though perfectly functional, the Zune lacks the iPod's "je ne sais quoi" appeal and as a result holds less than 3% of the MP3 market.