These pivotal moments are the history you don't want to repeat (and, maybe, provide grist for mills of those who always say "I told you so!")

by Neil McAllister/InfoWorld

25. IBM PS/2. The original IBM PC hit the market like lightning in 1981. Unlike earlier IBM computers, it was built with off-the-shelf parts instead of proprietary components, making it the most affordable business machine yet. But by the late 1980s, IBM found itself edged out of the market by Compaq and the other PC clone makers. Its solution? Try again with proprietary components, of course!
The Personal System/2 series, introduced in 1987, was meant to be "software compatible" with the PC, but its Micro Channel Architecture made it incompatible with existing hardware. The clones had no such problem. Like the disastrous PCjr before it and the PS/1 series to follow, the PS/2 convinced customers that lightning would never strike twice in IBM's PC division.

24. Virtual reality. In 1982, the movie "Tron" imagined a man traveling the eerie internal landscapes of a computer. Fifteen years later, the technology arrived to make it happen -- sort of.
Building a spatial interface for the Internet was all the rage in the late 1990s, owing in part to VRML (Virtual Reality Markup Language). The problem was, it didn't make much sense. The Web put the world of information at your fingertips; leave it to software engineers to find a way to send it back down the street, across a bridge, and up two flights of stairs.
The concept lives on today in Second Life, which seems to think the problem is not enough advertising. But the truth is that mainstream users have never warmed to VR. Wake us up when we can ride real lightcycles to work and meet our clients on the Game Grid.

23. Compression wars. What do you do when another software company copies your code and releases an improved version of your own product? Sue them into the ground, right? That's what System Enhancement Associates (SEA) thought in the 1980s, when Phil Katz released a clone of SEA's archive compression program, Arc.
Katz's hand-optimized assembly language provided better performance than the original Arc, but because Katz had borrowed code from SEA's product, SEA successfully sued for copyright infringement. Customers, however, felt betrayed. They saw SEA as a bully trying to stifle Katz's superior software. When Katz came up with his own high-performance archive format in 1989 -- called Zip -- they ditched Arc in droves, and SEA's business never recovered.

22. Apple OpenDoc. Long before the Cocoa and Carbon APIs earned raves from Mac OS X application developers, Apple put its weight behind another innovative programming technology. Called OpenDoc, it was a way for developers to build applications out of lightweight, modular components. After all, what is a word processor but a text editor, a spell checker, a file manager, and a few other modules all thrown together? With OpenDoc, developers could mix and match, building their applications out of all the best bits.
Unfortunately, the concept never caught on. As it turned out, most applications weren't really as modular under the hood as they appeared on the surface -- and it didn't help that those so-called lightweight components turned out to be memory hogs that ran like molasses. After five short years, the book on OpenDoc was closed.

21. Push technology. In 1992, PointCast had a clever idea: Why not make it possible to view stock quotes, headlines, and other information in real time, without browsing the Web? Instead, the PointCast client would "push" the information direct to the desktop, all day long.
The idea spawned a horde of imitators. Unfortunately, no one foresaw the strain that all that pushing would place on the limited Internet connections of the time. Network managers banned the client, and modem-based home users balked at the ads being pushed to them along with their sports scores.
News Corp. once offered $450 million for PointCast. Two years later, the push craze had evaporated, and it sold for a paltry $10 million.

20. Copland. Some fumbles can be recovered. And it's true; today, Mac OS X is an impressive operating system. But imagine how much further Apple could have gone if it had delivered its next-gen OS when it originally intended to, back in 1995.

Copland was meant to be the modern successor to the original Mac OS, but years of political infighting had hobbled Apple's development department. For all its superior engineering talent, it became clear that it was impossible for Apple to produce a modernized Mac OS on its own. Instead, it would buy Steve Jobs' NeXT OS and use that as the basis for the Mac OS X that ultimately shipped in 1999 -- ironic, considering that Jobs had left Apple over political infighting a decade earlier.

19. Gnu Hurd. When Richard Stallman launched the Gnu project in 1983, his goal was to build the world's first completely free operating system: kernel, tools, utilities, applications, documentation, and all. Good thing he didn't start from the bottom up.
Almost 25 years later, there is still no Gnu kernel. The Hurd, as the proposed kernel is known, should have been the Free Software movement's crowning achievement. Instead it's become the poster child for collaborative software development gone wrong, topping the lists of vaporware year after year. And it's a shame -- because wouldn't it be great if there was a free OS kernel for everyone to use?

18. Oracle Raw Iron. What's the best OS for your database server? Should you run it on Windows? Linux? AIX? Something else? Back in 1998, Oracle's answer was none of the above! Instead, Larry Ellison promised an "appliance" version of Oracle 8i, called Raw Iron, that ran atop the bare server hardware. No longer would Oracle customers need to worry about a separate support contract with an OS vendor: Oracle would handle the whole show.
Behind the scenes, prototype Raw Iron boxes ran a custom version of Sun Solaris, but it didn't matter. Customers had seen through Larry's hand-waving, anyway. When nobody bit, the project was quietly shelved -- just a few years before the market for network appliances took off.

17. B-to-b e-commerce. As the dot-com craze waned in the early 2000s, venture capitalists clung to a last-ditch idea: If all those startup e-commerce companies weren't striking gold with the consumer public, maybe they could ply their wares to other, more established companies instead? They called it b-to-b e-commerce, and a generation of would-be digital disintermediators was born.
The problem was that few of their potential customers were interested in cutting out the middlemen -- not if it meant trading them for an unproven online startup with a tiny sales force and no real experience in inventory management. In the end, though, the b-to-b players did deliver some excellent deals -- when their assets were offered up at auction.

16. Apple Newton. It's no iPhone, but by some measures the Newton still beats the pants off any PDA since. Rabid fans wax nostalgic about the Newton OS, and breathy rumors of a new Apple PDA remain a staple of Macworld Expos. Alas, the Newton never had a chance. Introduced in 1993, the Newton MessagePads were bulky, with lousy battery life. While Palm and Microsoft's PDA partners were building devices that could actually fit in your pocket, Apple answered with a full-sized keyboard and a clunky clamshell for the Newton eMate 300 in 1997, then threw in the towel as its losses mounted.
It's a shame. With some software tweaks to suit business users, the iPhone and the iPod Touch could get Apple back in the game. But given the bad taste left by Newton, who'd be brave enough to suggest it to Steve now? (Besides us.)

15. Palm OS Cobalt. The only thing worse than giving up on a viable market is to win it totally, then run it into the ground. What else can be said about Palm? Its devices were revolutionary, its competition from Microsoft laughable. Then came years of mergers, acquisitions, spin-offs, and rebranding. All the while, the products stagnated. When Palm finally delivered its Cobalt OS in 2004, the purported successor to the aging Palm OS failed to win any licensees.
Now, Palm is resorting to a Hail Mary: The next Palm OS, we're told, will be based on Linux. But when it might appear is anyone's guess, and by then it won't matter. We'll all be too used to this year's Treos, running Windows Mobile.

14. Netscape 6. The turning point of the browser wars came in 1997, with the release of Internet Explorer 4. For the first time, IE was better than Netscape Communicator. Not only was it faster, but it had more features and better standards compliance.
Netscape should have struck back immediately, but instead it dragged its feet. As Microsoft pressed ahead with IE5, Netscape's open source Mozilla project foundered, producing nothing but buggy "preview releases." When Netscape 6 finally appeared, years later, it was a bloated, sluggish mess. The war was lost, and now even the Netscape brand is scheduled to pass into oblivion.
Ironically, the former Netscape Communicator suite lives on as an open source project, called SeaMonkey -- presumably because it sounded great at first, but the real thing is a disappointment.

13. Search portals. Where are they now? At the height of the dot-com boom, Web surfers had a plethora of search engines to choose from: AltaVista, Excite, InfoSeek, Lycos, and many more. Today, the major players of the past are mostly dead. A few have soldiered on, such as Ask.com, but only after repeated redesigns.
Chalk it up to old-fashioned hubris. Instead of concentrating on their search offerings, the first-generation search engines fell victim to the portal arms race. They built up dashboards full of sports scores, stock quotes, news headlines, horoscopes, the weather, email, instant messaging, games, and sponsored content -- until finding what you wanted was like playing Where's Waldo. Neither fish nor fowl, they became awkward combinations of search portals and general-interest portals. The world went to Yahoo for the latter. And when an upstart called Google appeared with a clean UI and high-quality search, users told the other engines to get lost.

12. IPv6. Few topics spark more debate than IT's equivalent of global warming. According to some experts, the question isn't whether we will run out of IPv4 network addresses, but how soon. And there's no Kyoto controversy here; federal policy already requires that government offices transition to IPv6 by 2008. So why is everyone still dragging their feet?
Quite simply, IPv6 is a fix for a problem nobody has yet. Stopgap solutions such as NAT, while infuriating to network engineers, have proven effective. And IPv6 offers no compelling features to offset the headache of implementing it. In other words, until someone offers the equivalent of carbon credits for networking, IPv6 is one truth that's just too inconvenient.

11. Microsoft Passport. We all have too many online accounts and too many passwords to go with them. If Microsoft wants to save us some hassle by remembering them all for us, why not, right?
But Web users didn't flock to Microsoft's single sign-on service when it went live, and neither did partners. The idea was good, but the implementation was lousy. First came public debate over privacy concerns. The discovery of security holes in the Passport software was just the final straw.
To be fair, Microsoft's competitors had no luck with the concept, either. As it turns out, people think handing over their personal security information to a third party as a way to save effort is a bad idea. Who knew?

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