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Microsoft's 13 worst missteps of all time

Woody Leonhard | Jan. 15, 2013
DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

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.


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