Tech's all-time top 25 flops: No. 1 to 5
5. Digital rights management. Has any industry ever invested so heavily in a technology that its customers didn't want? Again and again, media companies keep racing to market with one new twist on digital copy protection after another, then offer up their own failures as "proof" that the market isn't ready for downloadable content.

It's strange, too, when you consider that every DRM scheme yet invented has been quickly compromised. Some experts believe that the whole concept of DRM technology is inherently flawed. Still, as encouraging as Steve Jobs' recent statements have been, it's difficult to speculate on when the media giants will give up on this harebrained idea. Greed is a powerful motivator.

4. Paperless office. Who needs paper? For years, office managers have been rubbing their hands at the notion that databases, spreadsheets, e-mail, and digital documents can replace traditional ledgers, forms, and faxes. But while saving the environment is a laudable goal, the truth is that it's actually harder to preserve digital records than the old-fashioned kind.

Increased regulatory pressures have helped fuel a cottage industry around information lifecycle management, but the real-life capabilities of these products are a far cry from their lofty ambitions. Meanwhile, digital record-keeping presents security and privacy risks unheard of in the days of locked filing cabinets. The paperless office may finally be here, but it's enough to make you wish for a good, old-fashioned memo pad.

3. iPod imitators. Apple has always been the underdog of the PC market. Maybe that explains the electronics industry's chronic habit of underestimating the iPod. Would-be competitors have come and gone, but go they do, swiftly, once customers get a gander at their second-rate hardware and atrocious interfaces. From Microsoft's ugly, feature-hobbled Zune to TrekStor's abortive plan to release a player under the cringe-inducing moniker i.Beat blaxx, it seems nobody can get it right, even with Apple paving the way.

Frustrated, SanDisk recently resorted to Swift Boat-style attack ads, referring to the Apple faithful as "iChimps." The question is, is it the iPod they hate? Or the millions of potential customers who refuse to settle for an inferior copy?

2. Windows Vista. What if you threw a party for the world's most revolutionary operating system and nobody came? Then again, by the time Windows Vista actually shipped, the "revolution" looked more like a failed coup.

Despite repeated delays, much-anticipated features such as WinFS and the Monad command shell never made it into the shipping version of Vista, even as its system requirements grew and grew. When the dust finally cleared, the new OS seemed like little more than a bloated rehash of Windows XP, touched up with fresh coat of 3D-rendered paint. Add sluggish performance, spotty driver support, UI annoyances, and a dubious application security model, and suddenly desktop Linux doesn't sound like such a crazy idea after all. Who knows what could convince risk-averse enterprises to make the leap to Vista now -- but hey, there's always Service Pack 1, right? Or maybe Service Pack 2.

1. Security. Computers influence every aspect of our business lives. We trust them implicitly to manage our records, compute our figures, and facilitate our communications. When will we ever learn?

Thirty years into the personal computer era, and it seems like security is only getting worse. Computer viruses and worms, though simplistic in comparison to any useful application, have proven as resilient as the common cold. The Web, e-mail, and instant messaging have given criminals unprecedented opportunities for fraud, scams, and electronic spying.

In 2007, corporations lost customer data to cyberthieves like never before. And today's vast digital repositories make for very juicy targets that can be copied onto a few DVDs slipped unnoticed in a jacket pocket. If auto manufacturers approached safety the same way that software makers handle security, we'd all be driving Ford Pintos and Yugos. And airline security would resemble the "systems" that buses use to catch fare-dodgers.

Now that we've built a digital world on an insecure foundation, the solutions for security are really hard – maybe too hard. We may just need to live with the fact that computer technology is largely unsecure, so caveat utilisator.

Top tech flops Nos. 21-25: PS/2, VR, compression wars, ...
Top tech flops Nos. 16-20: Copland, Gnu Hurd, Oracle Raw Iron, ...
Top tech flops Nos. 11-15: Palm OS Cobalt, Netscape 6, search engines, ...
Top tech flops Nos. 6-10: Itanium, Mac clones, e-currency, ...
Top tech flops Nos. 1-5: DRM, paperless office, iPod imitators, ...