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 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.

Microsoft misstep No. 9: Windows Ultimate

Windows Vista shipped in several versions, the most extravagant of which was Windows Vista Ultimate. Combining all of the features of Vista Business and Vista Home Premium, it also added the exclusive Windows Vista Ultimate Extras.

Ahem: "Windows Ultimate Extras are programs, services, and premium content for Windows Vista Ultimate. These features are available only to those who own a copy of Windows Vista Ultimate."

That's the promise. The reality was less impressive. Ultimate contained Windows DreamScene, a handful of videos to be used as desktop wallpaper; Hold 'Em Poker; three extra sound packs; and a puzzle game starring a robot -- and was later released free. The, uh, loyal Microsoft customers who spent an extra $100 for Vista Ultimate got burned big time.

Microsoft learned its lesson. Windows 7 Ultimate, under Sinofsky, only promised -- and delivered -- a combination of all the features in Win7 Home Premium and Professional. The loyal customers were never compensated.

Microsoft misstep No. 8: Windows Genuine Advantage

What does the then-richest software company in the world call its copy protection scheme? Why, "genuine advantage," of course.

In the halcyon days of Windows 95, 98, and 2000, anyone installing Windows had to provide a serial number. The serial numbers weren't checked against a master database, so the same serial number could be used to install multiple copies of Windows.

With the consumer version of Windows XP, Microsoft added a validation step, where a specific serial number was matched against a key constructed from serial numbers from PC components. The resulting combination is checked against a central database. Changing your motherboard or network card, or in some cases other combinations of hardware, triggered a revalidation. Fail the validation, and Windows wouldn't work -- you had to call Microsoft to beg for forgiveness.

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