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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

Predictably, the validation servers borked; false positives came to light. Microsoft got caught shipping data from unsuspecting PC users to the Microsoft servers once a day. Windows Genuine Spyware became the nom de guerre.

Howls, lawsuits, threats, cracks, and generally furious customers eventually drove Microsoft to backtrack. Reduced-functionality mode evolved into a paper tiger, with harmless balloon notifications about ungeniune wayward ways, and an irritating tendency to turn the desktop wallpaper black.

In Windows 7, WGA became Windows Activation Technology, no doubt to avoid the venom aimed at its predecessor. The newly renamed copy protection scheme retains its toothless nature, even in Windows 8. Microsoft can learn from its mistakes.

Microsoft misstep No. 7. Branding

I don't understand why Microsoft has such a terrible time with branding.

Some of the customer-confusing moves are just silly. In 1991, Microsoft jumped Word for Windows from Version 2 to Version 6, with no intervening version numbers. Word 2.0 was part of Office 3.0, but Word 6.0 was part of Office 4.0. When Microsoft released Office 95, it increased the version numbers of all of its components to 7.0: Word 7.0, Excel 7.0 (also called Excel 95; there was no Excel 6), PowerPoint 7.0 (there were no Versions 5 or 6), and Schedule+ 7.0, which morphed into Outlook.

Some of the branding is worse than silly. Stupid changes made years ago continue to confuse Microsoft users today. Consider how many email clients Microsoft supports at this moment. I can think of seven:

I could rant about most of those branding missteps, but allow me to concentrate on the last one. Can you believe that Microsoft intentionally threw away the name "Hotmail" -- one of the most widely recognized brand names in the world, right up there with Coca-Cola and McDonald's and Toyota and, yes, Microsoft -- turning it into something absolutely nobody understands?

That's worse than crazy. It's self-destructive.

Case in point: Microsoft's attempt to create a database of user IDs and associated data, including individuals' financial information. It all started with Hotmail: sign up for a account, and Microsoft stored the information you provided.

Then your Hotmail account suddenly became a Microsoft Passport, a fancy name for a single-login authentication service that Microsoft hoped would take over the Internet: Everywhere you go, the marketing material touted, you could log on with your Hotmail account, er, Microsoft Passport.  And if you put your credit card info into Microsoft Wallet (earlier called Passport Express Purchase), buying items anywhere on the Web would only take a couple of clicks.

The privacy groups went ballistic -- like the Joker, only less civilized.

Microsoft bobbed and weaved. To its credit, Microsoft hired one of its most vocal critics, to put reasonable limits on privacy incursion. The name of the service changed -- branding and rebranding as Microsoft Passport Network, MSN Passport, .Net Passport, Windows Live ID. Now we know it as a Microsoft account, and it's baked into Windows 8. The personal financial information came and went, and the terminology/branding seems to have stabilized: If Apple can have one Apple ID or Google a single Google account, you can certainly have a single Microsoft account -- if you can figure out how to get your old Zune, ZunePass, Xbox, and Windows Phone accounts switched over to a Microsoft account.


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