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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Hardware manufacturers had a different process for activating machines before they shipped. Volume licensees were given serial numbers that worked in bulk.

Windows XP SP1 cut customers some slack: It added a three-day grace period, so you could continue to use your Windows PC for three days while trying to get it reactivated.

Then the offal hit the fan. Over the course of several years, in many confusing steps, Microsoft rolled out its Genuine Advantage program to all Windows XP and later versions.

The earliest versions of WGA included a program called WGA Notifications that runs whenever you log on and validates your Windows license. They also included an ActiveX control that validated your license every time you tried to download specific Microsoft products, including Internet Explorer 7 and Microsoft Security Essentials. You were also prohibited from using Windows Update to get security patches (although you could download Critical patches manually). WGA reached its nadir in Windows Vista, where failing the WGA check meant your machine was put into "reduced-functionality mode," where you could go onto the Web for an hour at a stretch, before Windows locks up.

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:

  1. Outlook (Versions 2003, 2007, 2010, and 2013 all look and act differently)
  2. The Outlook Web App, which doesn't look or act much like Outlook at all
  3. Windows Live Mail -- formerly Windows Live Mail Desktop, now part of Windows Essentials, formerly part of Windows Live Essentials
  4. Windows Mail, which shipped with Vista, but looks and acts much like Outlook Express
  5. Outlook Express, shipping with Windows XP and still supported
  6. The Windows 8 Metro immersive modern Windows Store Mail app, which comes with Windows 8 (in spite of the name, you don't download the Windows Store Mail app from the Windows Store)
  7. Hotmail Outlook.com
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