2004: Windows Genuine Advantage. Understandably, Microsoft hates it when people pirate Windows. So it added multiple copy-protection measures such as activation and validation to Windows XP and Windows Vista. Collectively, they're known as Windows Genuine Advantage, which the company touts as a benefit to properly licensed users. But WGA asks paying Microsoft customers to jump through piracy-detecting hoops. Worse, it's been known to accuse them of stealing Windows and shut off functionality.
What it should have been called: Snarky answer: Windows Genuine Disadvantage. Serious one: Windows Anti-Piracy Technology.
2004: PlaysForSure. This logo program for services and devices that used Windows Media DRM may have been the single most inaccurately named item in the history of personal technology. The name exuded hubris, but PlaysForSure tracks often FailedToPlay on PlaysForSure-enabled devices--and, of course, they didn't play at all on the world's most popular MP3 player, arch-rival Apple's iPod. For Pete's sake, they didn't even play on Microsoft's own music player when it appeared. By the time Microsoft shut down the PlaysForSure-powered MSN Music service, it had already rolled PlaysForSure into the blandly named Certified for Windows Vista program, which doesn't promise much of anything.
What it should have been called: MusicCripplingWindowsMediaDRM. Or just plain Windows Media, which is what PlaysForSure was beneath the patina of marketing hype.
2006: 2007 Microsoft Office System. When Microsoft announced Microsoft Office 2007 in February 2006, it started calling the overall Office platform the "2007 Microsoft Office System," even though individual versions, such as the alarmingly wordy Microsoft Office Professional Plus 2007, kept the year at the end of the name. At the time, a Microsoft representative explained the distinction to me, but I barely comprehended it even then--it was as if the company wanted Windows 95 to be called 95 Windows in certain instances. Then there was the superfluous "system" on the end, which reminds me of how the Disney company insists on calling Disneyland the "Disneyland Resort."
What it should have been called: Microsoft Office 2007. Actually, that's what everybody outside the city limits of Redmond does call it.
2008: Windows Live Essentials: In September 2008, Microsoft announced that it was stripping three of Windows Vista's applets--Windows Mail, Windows Photo Gallery, and Windows Movie Maker--out of Windows 7. They would live on, but as free downloads, known collectively (along with other apps such as Windows Live Writer) as Windows Live Essentials. But doesn't the fact that Microsoft unbundled these tools from Windows prove that they're not essential? Bonus annoyance: Microsoft's decision to identify these downloadable freebies' under the Windows Live rubric (which usually applies to Web services) makes it even harder to define just what Windows Live means.
What it should have been called: I'm not sure that anyone gains anything by giving these applets a collective name. But something along the lines of Windows Bonus Material or Windows Extras would work.
Next: Six runners-up.