2001: HailStorm. Hail isn’t exactly a form of weather resplendent with positive associations: It kills crops, damages cars, blinds drivers, and is downright painful–and occasionally deadly–to people unfortunate enough to get pelted by it. Yet that’s the codename that Microsoft chose to associate with the plans it unveiled in 2001 to deliver an array of Web services and to store consumers’ personal information for use with Microsoft and third-party offerings.

The notion of Microsoft controlling so much private data proved instantly controversial; the company changed HailStorm’s name to .NET My Services, and then put the whole idea on hold And yet HailStorm wasn’t so different from services that Microsoft, Google, Facebook, and others offer today. I can’t help wondering whether it would have fared better if it hadn’t had a name that suggested a violent weather disturbance descending from the heavens to afflict us mere mortals.

What it should have been called: Microsoft Passport–a name Microsoft gave its online ID service even before it announced HailStorm–wouldn’t have been bad. Today, however, Microsoft Passports are known as Windows Live IDs (presumably to distinguish them from all those Windows IDs that have died).

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.

Runners Up: Six More Unfortunate Microsoft Names

Chkdsk. Even in the DOS era, it was unclear why the name of this venerable disk-checking utility skipped all its vowels; even with the eight-character filename limit it could have at least been Checkdsk or Chekdisk. Today, there’s no excuse for not calling it CheckDisk.

All Microsoft products called Messenger. Not that it’s inherently bad name. But there’s Windows XP’s Windows Messenger; there’s the unrelated command-line utility called Windows Messenger Service, famous mostly for being a security leak; and there’s the old MSN Messenger, which was renamed Windows Live Messenger in 2005. That’s at least two Messengers too many. To its credit, though, Microsoft didn’t change “Messenger” to “Message Explorer.”

Microsoft Office Word. And Microsoft Office Excel, Microsoft Office PowerPoint, and Microsoft Office Access. With Office 2007, Microsoft stuck in a superfluous “Office” in the middle of some of the best-known names in the history of software. Nobody noticed. Basic rule of thumb: If your customers don’t realize that you’ve changed your product’s name, you’ve failed.

OneNote. Merriam-Webster tells me that “one-note” means “monotonous.” Microsoft’s handy note-taking application deserves better.

The Road Ahead. Published in 1995, Bill Gates’s best-selling book famously didn’t predict the rise of the Internet, thereby utterly failing to live up to the visionary promise of its title.

Windows 95: Yes, seriously: By the time it finally shipped, 1995 was two-thirds of the way over, leaving the blockbuster new version of Windows sounding slightly stale from the get-go. And it ushered in the era of consistently inconsistent Windows names, from additional year-based ones (Windows 98, 2000), to inappropriately highfalutin’ modifiers (Windows Millennium Edition, Windows Vista) to mysterious acronyms (Windows XP).

Are there other tech-product names you find annoying and/or inaccurate–from Microsoft or from other companies? Or maybe even names you think are really good? Sound off in the comments.

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