we'd look back on the first hundred days and see if we can begin to find the answers to a few questions. Questions like: Are the new Pocket PCs really faster and easier to use? Are the new Pocket PC devices as small as their Palm counterparts? And the big question, are the new Pocket PCs a threat to Palm's dominance in the marketplace?

But before we tackle those questions let's review some PDA history.

Microsoft's history with PDAs began back in the early 1990s with exploratory devices called the WinPad and Pulsar, and an operating system called At Work OS. But it wasn't until the mid to late-90's, with the development of a new operating system called Windows CE, that Microsoft was poised to enter the PDA market.

In late 1996, Microsoft released Windows CE version 1.0, and third-party devices called Handheld PCs that used the new OS began shipping in early 1997.

By that time, Apple, whom some credit with starting the PDA craze when it released the first Newton in 1993, was nearing the end of its PDA life. Steve Jobs had regained control of Apple and was convinced that one of the keys to righting the struggling Apple ship was to concentrate on core products. And Newton was not a core product.

Apple discontinued the Newton in early 1998.

Some say Newton's demise was simply Jobs' way of embarrassing John Sculley, the man who'd coined the term PDA and who'd been an instrumental part of Jobs' ouster from Apple in 1985. But the early Newtons were plagued by handwriting recognition problems and hefty price tags; price tags which grew and grew over the years, as did the size of the devices. But what really spelled the end of the Newton was weak sales. Apple sold less than 300,000 of the devices and lost hundreds of millions of dollars in the process.

Meanwhile, in April 1996, Palm Computing, which was owned by U.S. Robotics at the time, released its Pilot 1000 and Pilot 5000 devices. A key selling point for the new PDAs was price. The Pilot 1000 sold for $299 and the Pilot 5000 sold for $369, far below the Newton MessagePad 130 ($799) and the MessagePad 2000 ($949). And the Palm Pilots were small, lightweight and simple to use.

The rest is history.

Palm sold millions of its electronic organizers, mostly to people looking to automate the tasks previously relegated to their Filofaxs, DayTimers and Franklin Planners.

Microsoft, meanwhile, had a different agenda than either Apple or Palm. While Apple was a hardware and software company that felt a PDA was a replacement for your desktop computer, and Palm was a hardware and software company that felt a PDA was an accessory for your desktop computer, Microsoft was neither.

Microsoft was a software company looking to license as many copies of its Windows CE operating system as it could. It envisioned Windows CE as an embedded operating system that could be configured for any consumer device. It toyed with the idea of creating its own handheld devices at first, but eventually decided to stick to its software roots.

In retrospect, this embedded OS philosophy is something that many industry experts believe is what has held Windows CE back in the handheld arena. Many believe Windows CE to be too big and too slow. In fact, Microsoft has made very few inroads in the embedded arena.

So when it came to handheld computers, Microsoft was forced to listen to manufacturers such as Hewlett Packard, instead of its own vision of a small, pen-based PDA, which dated back to the Pulsar. Instead, Microsoft heeded HP's request to include keyboard support in its new OS.

So in 1997, while Palm was gobbling up the PDA market, Microsoft's licensees were releasing larger, more expensive, keyboard devices to the market. They were gambling that Apple was correct--that consumers wanted a device that could do what a laptop could do, only smaller--and that it was either Apple's poor execution or its early entry into the market that caused it to fail.

But the gamble proved wrong. Consumers, it seemed, wanted exactly what Palm was giving them--a small, inexpensive, easy-to-use, pen-based device.

So in 1998 Microsoft and the Windows CE device manufacturers came out with smaller devices, called Palm-sized PCs. It was their second gamble. This time they conceded that people wanted a smaller pen-entry PDA, but they still believed that people wanted to do more with these devices--not simply PIM functions--or they eventually would.

So they built the new Windows CE Palm-sized PCs with faster processors, more memory and storage, and provided plenty of expandability into the world of peripherals and add-ons.

But there's one thing they lacked: market share. Palm had beaten them out of the gate and had grabbed more than 70% of the PDA market. More importantly, Palm had grabbed "mind share." The term "Palm Pilot" had become synonymous with PDAs, just as Kleenex had with facial tissues.

In early 1999, Microsoft tried color screens and faster processors, but nothing stemmed Palm's rising tide. By mid-year Microsoft faced another decision, and a reexamination of its second gamble. It decided to listen to the industry pundits who blamed Microsoft's do-everything OS strategy and the size and complexity of the Windows CE devices. It embarked on a rewrite of the Windows CE operating system that would make it faster and simpler. And they convinced the device manufacturers to design sleek, new devices with compelling hardware features.

On April 19, amid the noise of New York's Grand Central Terminal, Microsoft and its partners, Casio, Compaq, Hewlett Packard and Symbol, played what some say is its final card, the Pocket PC.

So was it worth the gamble?

One point of controversy and discussion has been the name used for the Windows CE-based devices. It's a well-known fact that Microsoft originally tried to use the name Palm PC. But Palm Computing, and its parent 3Com, filed a lawsuit to prevent them. Eventually the rivals settled their dispute out-of-court, a settlement which allowed Microsoft to use the clunky name Palm-size PC.

Coincidentally, Palm faced a product naming issue early in its existence when Pilot Pen Corporation asked Palm to stop using the name Pilot for its product.

But since the start, the moniker Palm-size PC was just too much of a mouthful, and not very catchy.

So when Microsoft set about on the OS redesign, they decided to address the naming issue. First, it dropped the tagline Powered by Windows CE for the catchier Windows Powered. Next, it ditched Palm-size PC in favor of Pocket PC.

Most people praised these actions, saying it is a good start toward eliminating the consumer confusion between Palm organizers and Palm-size PCs. Yet few journalists explored the deeper roots of Microsoft's product name game.

Microsoft had used the word Pocket in naming its software suite. There's Pocket Outlook, Pocket Internet Explorer, Pocket Access, Pocket Word, Pocket Excel, and Pocket PowerPoint (and the soon-to-be Pocket Money).

So why didn't Microsoft simply call it Pocket PC from the start?

Well, some say it's because Pocket PC was trademarked. According to US Patent and Trademark Office records, Pocket PC, Inc. of Treasure Island, Florida, was granted a trademark on Pocket PC in 1994. However, this trademark issue seemingly didn't stop several other firms, including Addonics and DIP, both of whom released products called Pocket PC.

But there's another catch. Pocket PC, Inc.'s trademark was granted for only 6 years, under Section 8 of the Lanham Act. In other words, it expired in 2000.

On January 6, 2000, the day of Microsoft's original Pocket PC announcement, the Internet domain www.pocketpc.com was owned by a small non-technology company. However, on January 7th, the domain registration was changed to Weinberg Legal Group, an intellectual properties and Internet law firm based in Phoenix, Arizona.

And on January 20th, Microsoft re-launched the site as its own.

So Microsoft finally had Pocket PC in its pocket. And isn't that where you keep the electronic wallet that Bill Gates always talks about?

Microsoft planned a huge product launch on April 19 at Grand Central Terminal in New York City to kickoff the new Pocket PCs. Journalists and developers were required to sign non-disclosure agreements to even steal a peak at the new OS or a new Pocket PC prior to the launch. And manufacturers promised to have devices in stores for consumers to purchase.

The idea was to create anticipation and excitement, and then be ready to deliver the goods. And it was all working fine until mid-March when the leaks began.

On March 19th, Brighthand.com released some pre-production pictures of the Compaq iPAQ Pocket PC that had been leaked to them from a source in Europe. And two weeks before the launch, pictures of the new Jornada 545 Pocket PC from Hewlett Packard made their debut in the May issue of Computer Shopper magazine.

And a week prior to the official launch, many users caught glimpses of both the HP and Casio Pocket PCs on the companies' web sites when they "live-tested" Pocket PC web pages late one night.

Still, this all served to create even more excitement in the PDA community.

Something remarkable occurred at the official Pocket PC product launch on April 19. Microsoft CEO Steve Ballmer acknowledged Microsoft's inability thus far to "inspire and excite" consumers with its Palm-size PCs.

"We've enjoyed some success," said Ballmer. "But not what we wish we had. We made some mistakes."

This dose of humility stunned a number of journalists and industry watchers, but when all was said and done that day there was a distinct aura of "nice devices, but let's see how they'll sell" amongst the attendees.

Casio and Hewlett Packard managed to get new devices on store shelves for the launch. But many consumers were disappointed when Casio's new Cassiopeia E-115 Pocket PC ($599) was simply the same old Palm-size PC form factor with the new Pocket PC poured inside. No faster processor, no sleek design, no USB. So while it's still an excellent device, it was not what consumers expected.

Hewlett Packard, on the other hand, unveiled a sleek new Pocket PC. The Jornada 540 series is approximately the size of a Palm IIIc but about 30% heavier. While it was a fetching new design, and HP added USB support and stereo sound, not much else changed about the Jornada from a physical standpoint from its Palm-size PC predecessor. But the new operating system did prove to be significantly faster and HP provided the best suite of additional software included with any PDA.

Hewlett Packard has reported extremely strong sales of the new device, but it has had difficulty fulfilling orders for its most popular model, the Jornada 548 ($599). This is due to the component shortage, which include the shortage of LCDs.

Compaq broke the most ground among device manufacturers with its new iPAQ H3600 series Pocket PC ($499). The iPAQ has become the PDA equivalent of the Cabbage Patch doll, with its overwhelming consumer demand and short supply, in part due to the same component shortages affecting HP.

And there's reason for the high demand. The iPAQ is fast (it sports a 206 megahertz Intel StrongARM processor), is as small and light as the Palm IIIc, and has a color

screen that's incredibly readable both indoors and outdoors. It's already been named Editor's Choice for best PDA by several computer and business magazines.

Yes, the new Pocket PC operating system is faster and easier to use. And, yes, the new Compaq iPAQ Pocket PC is as small as its Palm counterparts, while the Jornada is as small but not as lightweight.

Whether the Pocket PCs will be able to cut into the market share that Palm's managed to carve out over the past three years has yet to be seen. It will take creative and persistent advertising and compelling applications for professionals in vertical markets, including healthcare.

But the key to Pocket PC's hopes for success in the PDA marketplace is consumer "mind share" and that'll be the toughest nut to crack.

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