8. PalmOne Treo 650 (2004)
The product: The Treo--the telephonic scion of the pioneering PalmPilot PDA--wasn't the first smartphone. It was, however, the first on that nailed the concept, starting with the Treo 180 in 2002 and continuing through a series of increasingly powerful and refined models manufactured by Handspring, and then PalmOne (which later reverted to its original name, Palm).
The bad things: In 2004, the Treo 650--successor to 2003's Treo 600--added a higher-resolution screen, Bluetooth, a better camera, and a removable battery. The new device sold well and received good reviews. But it also presented users with an unappetizing platter of hassles. For one thing, the new nonvolatile file system allocated space less efficiently than the previous file system had, leaving the phone with only 23MB of available memory--a fact that some purchasers discovered only when they learned that the data they tried to transfer from their Treo 600 wouldn't all fit in the new model. Treo 650 owners wound up receiving free 128MB SD Cards by way of compensation, but many still complained of crashes. And some found that defective SIM trays on the 650 caused spontaneous rebooting.
The aftermath: Palm continued to sell Treos (including both Palm OS and Windows Mobile models), but the brand had lost most of its luster. Today, Palm quietly offers one last Treo model, but it has bet the future of the company on the WebOS-equpped Pre and Pixi. May they age more gracefully than the once-beloved Treo did.
9. Hotmail (2007)
The product: Founded in 1996 and owned by Microsoft since 1997, Hotmail is the original free Webmail service, and it remains one of the world's most popular ways to send and receive e-mail.
The bad things: In 2005, Microsoft began beta-testing an all-new version of its e-mail service, initially code-named "Kahuna." The service's look and feel were reminiscent of the company's Outlook e-mail client, and Microsoft announced that it would retire the Hotmail name in favor of Windows Live Mail. Unfortunately, many users found the new interface cumbersome and liked the old Hotmail--including its moniker--just fine. In short, they were far less enthusiastic about the changes than Microsoft was.
The aftermath: One benefit of lengthy beta-testing periods is that companies have more time to undo unpopular decisions--even ones they've been proudly trumpeting. In February 2007, Microsoft announced that Hotmail would be changing its name to...Windows Live Hotmail. And by the time the company began rolling out the official version in May, it had also decided to leave the old Hotmail interface in place as the default. The new interface it had been toiling on for so long became strictly optional.
10. iMovie '08 (2007)
The product: Apple's decade-old video-editing package is one of the stalwarts of the company's iLife suite, whose excellence is one of the most compelling arguments for buying a Mac. Over the years, iMovie has also influenced plenty of video editors for Windows.
The bad things: To hear Steve Jobs tell it, iMovie '08 started out as a side project by an unnamed brilliant Apple engineer but was so impressive that it became iMovie '08. It was less an upgrade from iMovie HD 6 than a new product that happened to be called "iMovie." It had a different interface and omitted scads of iMovie HD 6 features--you didn't even get a timeline of your movie. David Pogue of the New York Times called it "a step backward" and an "utter bafflement." And his assessment was polite compared to the response of some iMovie enthusiasts.
The aftermath: The chorus of disapproval over iMovie '08 was so deafening that Apple did something most unusual: It made the old version of the app available as a free download for disgruntled users. More important, the "brilliant engineer" (video-editing genius Randy Ubillos, we later learned) went back to the drawing board and came up with iMovie '09--an upgrade that earned positive reviews.
Former PC World Editor-in-Chief Harry McCracken now blogs at Technologizer .
Can you think of any other examples of tech products whose major upgrades turned out to be utter letdowns? Leave a comment and share the gory details.