Microsoft's 13 worst missteps of all time

DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

Over the years, Microsoft's made some incredibly good moves, even if they felt like mistakes at the time: mashing Word and Excel into Office; offering Sabeer Bhatia and cohorts $400 million for a year-old startup; blending Windows 98 and NT to form Windows 2000; sticking a weird Israeli motion sensor on a game box; buying Skype for an unconscionable amount of money. (The jury's still out on the last one.)

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Along the way, Microsoft has had more than its fair share of bad mistakes; 2012 alone was among the most tumultuous years in Microsoft history I can recall. This year you can bet that Redmond will do everything in its power to prove 2012 naysayers wrong. To do so, Microsoft must learn from the following dirty baker's dozen of its most dreck-laden decisions, the ones that have had the very worst consequences, from a customer's point of view.

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Microsoft misstep No. 13: DOS 4.0In July 1988, IBM and Microsoft released IBM DOS 4.0, and the wheels fell off with data-eating bugs, corrupted disks, and mismanaged memory. Fingers have been pointing ever since. Microsoft's side says IBM botched the testing; IBM's side says Microsoft shouldn't have expected IBM DOS 4.0 to work on non-IBM hardware.

IBM shipped the partial-fix IBM DOS 4.01 in September, but Microsoft took two more months to ship the clearly identified, and differentiated, MS-DOS 4.01. Many people who bought new computers in late 1988 insisted on DOS 3.3, not 4.0 or 4.01. Customers didn't know what to make of the new versions and largely stuck with the devil they knew, 3.3.

Microsoft misstep No. 12: The evil cuties Bob, Clippy, and RoverSymbolized by a big yellow blob with nerdy glasses, Microsoft Bob -- code-named "Utopia" -- stands as the quintessential Microsoft failure by which all others must be measured. In a departure from the menu-based interface for Windows 95, which was released seven months after Bob, Microsoft Bob's main screen looked like a cartoon living room, with graphic links to a word processor, finance application, calendar, Rolodex, checkbook, and other programs. Click on the grandfather clock's face and the calendar program appeared. Click on the envelope and the email program sprang to life -- Bob cut a special deal with MCI Mail whereby, for just $5 per month, a Bob owner could send up to 15 emails per month, absolutely free.

Customers could add tiles, er, shortcuts to new applications installed on their Bob-ified computer, and the shortcuts' pictures would appear in the immersive Start menu, uh, cartoon living room, inside picture frames or shipping crates. The living room could be personalized with various colors, decorations, and themes. Stop me if this sounds too familiar.

The eponymous Bob himself looked a lot like Bill Gates -- at least, as much as a smiley face with glasses can resemble the world's greatest philanthropist. Microsoft Bob shipped with cartoon helpers bearing distinctive appearances and personalities: Scuzz the Rat ("Couldn't care less about you. Seldom offers help."); a dog named Rover ("Easy to work with, friendly and helpful. Tries to be your best friend."); Chaos the Cat; Digger the worm; Shelly the turtle; Java the coffee-swigging dinosaur; and a half-dozen more.

Released in 1995 and abandoned in 1996, Bob didn't live very long, but he left quite a legacy -- I mean, in addition to his obvious design influences on Windows 8.

The Rover cartoon helper in Bob appeared, unchanged, as the Search Companion in Windows XP's Windows Explorer. Rover and his similarly designed cohorts -- Merlin the magician, Earl the surfer, and Courtney (the courtesan?) -- offered to help perform local searches on the Windows XP desktop.

More insidious, a perky offshoot known as Clippy "It looks like you're writing a ransom note. Would you like help?" appeared in Office 97. Clippy (and the Dot, Hoverbot, the Einstein-reminiscent Genius, Scribble the cat, Power Pup, Links the cat, Rocky the dog, and Will as in Shakespeare) shipped with Office 97, 2000, and 2003, only to be tossed out on his curled ear with the arrival of Office 2007 and its equally cloying Ribbon interface. I note in passing that Steve Sinofsky was in charge of those Clippy-fied versions of Office.

Another big legacy for Microsoft Bob: Melinda French, product manager for Microsoft Bob, became Mrs. Bill Gates in 1994, while development on Bob was in its final stages. Melinda's a very private person, a driving force for the Bill & Melinda Gates Foundation. Even the people who put together their wedding had to sign NDAs.

Microsoft misstep No. 11: Zune, Kin, Courier, Windows Mobile, and missing the consumer mobile boatThese days, most consumers figure that Apple created the tablet market with its first iPad. Not true: Microsoft has been nipping around the fringes of the tablet market for years. You may not know that Apple had an earlier failure -- a portable of sorts, if not a tablet. In 1989, Apple revealed its first portable computer: a 4-inch-thick, 16-pound behemoth dubbed "Macintosh Portable." The lead-acid batteries had to stay in the machine because it wouldn't run directly on AC power. And it cost only $6,500.

After the luggable MacBrick and the Sony Walkman, but before the iPad, came Apple's iPod, and that's where Microsoft's Zune enters the picture. Apple scored big successes with the iPod in 2002 and 2003. Microsoft started designing the Zune -- portable player, Windows software, music service to compete with the iPod and iTunes -- around the same time. By the time Zune came to market in 2006, Apple already had the iPhone under development. The iPhone ultimately rolled over the iPod, the Zune, and just about every piece of portable consumer electronics ever made. After years of sales that hovered near zero, Microsoft officially killed the Zune in June 2012, with the Zune services side morphing into Xbox Music and Xbox Video -- two products best known to Windows consumers for sporting their own tiles on the Windows 8 Metro Start screen.

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