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2007: Vista's woes continue with WGA problems
Besides widespread security problems, Windows XP had been burned badly by piracy. One of the most important additions in Windows Vista was a new anti-piracy infrastructure that mixed product activation and ongoing validation to verify that an installation was valid ("Genuine," in Microsoft's curious marketing-speak).
The Windows Genuine Advantage program was an absolute mess in 2007, with many innocent customers finding themselves accused of piracy when they installed a new program or changed a hardware device. A Microsoft Knowledge Base article early in 2007 admitted: "This problem does not occur because of an issue in the installed program or device driver. This problem is caused by a system problem in Windows Vista."
By 2008, most of the user-hostile problems in WGA had been resolved and the system worked as intended. But the damage was done.
(For a depressing history of Vista's anti-piracy initiatives, see "Microsoft finally earns a passing grade (barely) for WGA.")
2008: Apple's 'Get a Mac' ads take dead aim at Microsoft
Apple's "Get a Mac" campaign started with TV ads in 2006, but it hit its stride in 2008 with a series of ads that mercilessly and effectively lampooned the problems of Windows Vista. One of the most direct was the "Calming Teas" ad, shown here. PC, played by John Hodgman, showed off his “Vista-stress-releasing bath salts and calming teas like Crashytime Chamomile and Raspberry Restart…”
2009: Windows 7 is the anti-Vista
In 2007, I wrote about the many problems of Windows Vista in a post titled "Vista isn't Me2, it's Win95 + 12 years." In that post, I offered a prediction: "If history repeats itself, Microsoft will release its next Vista update in 2009 or 2010, after a low-profile, secretive beta cycle, and it will be greeted as finally delivering on the promise of what Vista should have been all along."
That's pretty much exactly what happened. Under the leadership of new Windows boss Steven Sinofsky, Microsoft released Windows 7 right on schedule. OEMs were prepared this time, and there were few underlying architectural changes to cause problems. Windows 7 wasn’t perfect, but it was greatly improved over Windows Vista. And that "evolutionary" release was enough to make it one of Microsoft's biggest successes ever.