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

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Microsoft didn't just miss the boat with Zune. It watched and waved and heckled as the boat roared past. In 2007, Steve Ballmer told USA Today, "Now we'll get a chance to go through this again in phones and music players. There's no chance that the iPhone is going to get any significant market share. No chance. It's a $500 subsidized item. They may make a lot of money. But if you actually take a look at the 1.3 billion phones that get sold, I'd prefer to have our software in 60 percent or 70 percent or 80 percent of them, than I would to have 2 percent or 3 percent, which is what Apple might get."

Of course, Apple's income from the iPhone currently exceeds Microsoft's income -- from all sources.

Ballmer was right about one thing. We got a chance to watch consumer markets unfold with phones and music players. Zune failed miserably. Windows Mobile accounted for 15.7 percent of the U.S. mobile market in January 2010, according to comScore, but in two years Microsoft's flagship mobile product slipped to 3.9 percent. Outside the United States, Windows Mobile never amounted to half a hill of beans.

Then there was the Kin, the short-lived square-ish mobile phone with social networking aspirations. In a move reminiscent of "The Cat in the Hat," in 2010, we were offered Kin One and Kin Two. Like Thing One and Thing Two, the Kin was locked in a software box -- a client-server architecture that didn't allow third-party apps -- although the hardware was based on an ARM design. Verizon started selling Thing One and Thing Two in May 2010; 48 days later, Verizon gave up and sent all of its unsold Kins back to Microsoft.

Last month, Wired ran a series of leaked internal Microsoft videos that show pre-release testing of the Kin, and the results were devastating: Testers couldn't figure out how to perform even the most basic functions. If you bought a phone, you would expect to be able to make a call with it, right? Silly mortals. Heaven only knows why Microsoft continued the project.

Then there's the tablet debacle. Bill Gates talked about the Tablet PC in his Comdex Fall 2000 keynote, and Tablet PC general manager Alexandra Loeb gave the details in a Microsoft press release from November 2000:

No compromises. Immersive. Twelve years ago. Thankfully, she didn't mention "fast" or "fluid."

The first Windows XP Tablet PC Edition tablets appeared in 2002 and drew loud applause from a small group of fans, along with skepticism from many corners. Ultimately, the market spoke. Windows Tablet PC hardly rates a footnote.

Did Microsoft learn its lesson? Consider that in 2006, Microsoft hooked up with Intel and Samsung to work on Project Origami, the Ultra-Mobile PC (UMPC) effort that culminated in a small handful of touch-sensitive machines, some of which ran Windows Tablet PC Edition. Slow, clunky, battery-deprived, and almost universally despised, the Origamis hardly broke the consumer surface.

Then came the Microsoft Courier, arguably Microsoft's most innovative mobile device to date: dual 7-inch touchscreens, hinged in the middle as a book; high-resolution (for the time) camera. Nobody knows for sure, but reports say it would've weighed about a pound, sported Wi-Fi, an inductive charger, and a Home button, driven by an ARM Nvidia Tegra processor. The tile-less Infinite Journal interface would look more like a diary and offer touch or stylus access to a contact list, task organizer, free-form drawing program, email, browser, and maybe even an e-reader.

Reports of the Courier began circulating in 2008, just after the Origami went down in flames and shortly before rumors started leaking about the iPad. As best as anyone can tell, the project was killed in 2010, soon after the first iPad shipped. Ballmer spiked it in a shoot-out between the Courier's biggest proponent J Allard and Steve Sinofsky, who was busy consolidating his vision of Windows 8 on a tablet and didn't want to get sidetracked (or sideswiped) by the Windows CE-based Courier. Ultimately, Sinofsky won, the Courier died, and both J Allard and his boss Robbie Bach left Microsoft shortly after, a brain bust that has significant repercussions to this day.

Does Microsoft "get" consumer mobile? A couple of decades and multiple billions of dollars later, that's still a pertinent question. You can draw your own conclusions.

Microsoft misstep No. 10: Bad Windows: Do they run in cycles?Windows has had some great runs: Windows 3.1/Windows for Workgroups 3.11, then Windows 95 drove most of the computing world for years. Windows 98 came on strong, and Windows 2000 drew some converts.

But then it all went to Hades in a handbasket. Windows Mistake Edition (officially called "Me" for no discernible reason) was like a Windows 98 service pack, with a couple of features and a lot of bugs thrown in for good measure. Windows Me was, deservedly, the last version of Windows based on the old Windows 9x kernel, which at its heart ran on DOS.

Whistler, better known as Windows XP, came as a breath of fresh air. Built on the Windows NT kernel, XP's reign ran unopposed from its release in 2001, until the appearance of Vista in 2007. Segue to the hisses and boos.

Vista, I'm told, is still listed in the Encarta dictionary as a profane word (or it would be, if Encarta hadn't bit the bucket in 2009). Released to businesses in 2006 and consumers in 2007, Vista tried to improve on XP's security, but only succeeded in alienating an entire generation of Windows users.

Then came Windows 7, and all was right with the world once again. Proponents of the "good Windows, bad Windows" analysis claim that consumer versions of Windows run from great to lousy and back again. That's certainly a discernible trend from Windows 98 onward.

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