4. Microsoft Word 6.0 for Mac (1994)
The product: Microsoft and Apple may be the tech world's most inveterate archrivals, but that hasn't stopped Microsoft from being a major developer of applications for Apple's computers. It released Word for Mac in 1985--two years after the first version of the word processor appeared for Microsoft's own MS-DOS--and it sells an updated version of the application to this day as part of Office 2008.
The bad things: Word 5.0 for Mac, which shipped in 1991, had been a well-reviewed hit. But for the next major upgrade, Microsoft decided to focus on creating a Mac version of Word that matched the features of Word for Windows. So it abandoned all the work it had done on the previous Mac edition in favor of a version that was based on Word for Windows. The result? Word 6.0 felt like a bloated, buggy invader from the Windows world--even the keyboard shortcuts had changed. Mac fans went berserk, and version 6.01 didn't do much to calm them down (scroll to page 29).
The aftermath: Microsoft learned a lesson. Word 98, version 6.0's successor, was a strong enough app that Macworld named it and the rest of Office 98 as its Software Product of the Year. "[For] the first time in a long time," the magazine enthused, "Microsoft seems to actually understand what the elegance of the Macintosh is all about." The company also split Mac development off into its own group, the Mac Business Unit, shielding it from the unhealthy, Windows-centric influence of the rest of the Office team.
5. Starfish Sidekick 99 (1998)
The product: No relation to the T-Mobile smartphones--which have problems of their own--Sidekick was an early PIM. Debuting in 1983 as the first blockbuster product developed by1980s software wunderkind Borland International, it later traveled with Borland founder Philippe Kahn to his new company, Starfish Software.
The bad things: By the late 1990s, many PC users were ticked off over bloatware--software that bulged with nonessential features and gobbled up excessive disk space. Kahn responded with the appealing-sounding concept of "slimware." But Sidekick 99 wasn't just slim; it was positively emaciated. Aside from some new PDA syncing features, almost all of its changes involved removing features. Though the program was a trim 6MB in size, it had lost the earlier Sidekick's phone dialer, many of its importing and exporting features, its ability to output HTML calendars, and even its spelling checker. No wonder the predecessor, Sidekick 98, felt like the upgrade.
The aftermath: Six weeks before Sidekick 99 shipped, Kahn sold Starfish to Motorola, which said it would use the new acquisition's mobile-synching technologies to "create a new generation of wireless devices that exchange information with each other as well as with a wide array of information sources, including PCs, the Internet and wireless service providers." Instead, it didn't do much of anything with Starfish. And poor Sidekick got lost in the shuffle: The dumbed-down Sidekick 99 was the sad final version of a venerable PC mainstay.
6. Netscape 6 (2000)
The product: Before the rise of Microsoft's Internet Explorer, Netscape Navigator was the king of browsers and had introduced most of the computing public to the World Wide Web. And once Microsoft began pouring resources into IE, Navigator stood as its fiercest, most formidable competitor.
The bad things: Somewhere along the way, Netscape got so distracted by side issues--such as its enterprise software efforts and its purchase in 1998 by AOL--that it forgot to pay attention to its namesake browser. Engineers worked on Netscape 6 (which dropped the "Navigator" from its name) for a ridiculous 32 months before releasing it in November 2000. The first version of the browser built on the open-source Mozilla code base, Netscape 6 looked attractive and loaded pages quickly, but it was plagued by bugs and slow load times, prompting even long-time Navigator loyalists to abandon ship. Netscape eventually polished up the browser, but it was too late: By then, Internet Explorer's market share surpassed 90 percent.
The aftermath: Netscape 6 eventually bequeathed its flagship status to Netscape 7, which in turn gave way to Netscape 8. In 2007, AOL released Netscape Navigator 9--yes, the "Navigator" returned--but announced later that year that it was killing the browser. Still, the story of Netscape has a happy ending, in a roundabout way: The hugely popular Firefox is based on a modern version of the same open-source Mozilla code that powered the underwhelming Netscape 6.
7. Intuit TurboTax 2002 (2002)
The product: Taxes are unavoidably...taxing. But Intuit's TurboTax has long been the best-seller among applications designed to make paying Uncle Sam a little less arduous.
The bad things: By its very definition, tax software tends to be something that people pay for and then use only once. In 2002, Intuit decided that too many folks were skipping the "pay for" part, so it hobbled TurboTax with a product-activation scheme designed to defeat piracy. The security process required users to run a second program--one that prevented them from installing TurboTax on more than one computer and that sometimes failed to grant paying customers access to the software, period. The hassles prompted a class-action suit, and rival H&R Block ran ads touting the lack of copy protection its competing TaxCut software.
The aftermath: Despite the controversy, Intuit insisted that it was merely defending its intellectual-property rights, and refused to back down. But only for awhile: In May 2003, it announced that it was dumping product activation. The company apologized to users for having inconvenienced them, but it also conceded that the anticopying technology hadn't generated increased sales as anticipated. TurboTax remains DRM-free to this day, though more and more users pay for the piracy-proof Web-based version rather than for the boxed software.
Next: Treo 650, Hotmail, and iMovie '08