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Compaq's iPAQ PocketPC: The Multi-Purpose Multimedia Handheld

by Dale Dougherty

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As a Palm III user, the first thing I noticed about Compaq's iPAQ was the brightness of the color screen. I found it alluring and wanted to keep looking at it. I wanted to hold iPAQ and see how it felt in my hand. Just like that, I had a new interest in handhelds.

When the batteries died on my Palm III a month ago, I realized that I wasn't using it as much as I had been. My primary reason for using a Palm was to maintain a copy of my contact and calendar information; I used it as a PIM (personal information manager). I bought a modem for the Palm but I never found it useful for e-mail and Web browsing, largely because of the legibility of the screen. At the same time, my laptop was getting smaller and easier to carry around, so I found that I relied on it less as a PIM. Thus, I began allowing the Palm III to sit unused in my briefcase.

The Compaq iPAQ

The Compaq iPAQ.

I saw the iPAQ at BestBuy. I was looking to see if there were any new MP3 players on the market. (The original Diamond Rio I bought had died and I never replaced it.) The iPAQ was lightweight and slim and the chrome exterior was cool, almost slippery, in my hand. To begin using the iPAQ, I popped the stylus from its hole in the top by pressing a button. This relatively minor feature -- securing the stylus -- immediately appealed to me. I kept losing the pen on my Palm III. In a few seconds, I was able to launch the Windows Media Player and play a sample MP3 file. After a few minutes with the iPAQ, I was ready to buy it, purely on impulse, but they were out of stock at BestBuy. (I wondered if that was a good sign indicating unusual demand for the device or just unresponsiveness on the part of the store or the manufacturer.) Subsequently, I heard that the iPAQ was hard to find and that it was selling on eBay for twice the price.

So I was forced into doing a little online research. Having noticed the name "Pocket PC" on the chrome faceplate of the iPAQ, I typed in www.pocketpc.com and found a Microsoft site with a list of resources. As Rob Baldwin at Pocketnow.com points out in A Review of the Pocket PC operating system, the Pocket PC is the name used for the operating system, which is also known as Windows CE 3.0, and a class of hardware devices that includes not only the Compaq iPAQ but Casio's Cassiopeia E-115 and Hewlett-Packard's Jornada. (Note: The marketing folks at Compaq have decided to use the iPAQ name for a desktop series of computers as well as this handheld, so it's a little confusing. Technically, I have the iPAQ H3600.)

Here is a summary of the specs for the iPAQ unit:

I ordered mine online for $499 from Microwarehouse.com. It arrived the next day, and soon I had a new device to show to the other Palm users around the office. I found myself going through the following set of features when demonstrating the new device:

In short, the iPAQ is not just a PIM. It does everything that the Palm set out not to do, plus most of what it already does so well. Even so, with so much going on, the iPAQ retains its simplicity. Some of that can be attributed to how well the iPAQ integrates with the PC. There seems to be a close partnership between the PocketPC and the PC so that the handheld doesn't have to do so much work itself.

Why is it that the Compaq iPAQ can succeed today, unlike Apple's Newton, which many thought failed because it tried to do most of what a PC could do? The insight behind the Palm was to do a lot less: just focus on being a PIM. However, much has happened since the Newton and even the Palm were first introduced. While the PC has remained the same, we have seen a proliferation of small devices, including PDAs, but also cell phones, pagers, digital cameras, MP3 players, digital voice recorders, Gameboys, and specialty reading devices such as the Rocketbook. There seems to be an opportunity -- a new niche -- to begin combining some of these functions in a single device.

That is what makes the Compaq iPAQ Pocket PC a multi-purpose, multimedia device, taking it to a level of functionality above the Palm. This is not to say that the Palm is no longer viable. Undoubtedly, if you only wanted to manage your contacts, the Palm is a cheaper solution. The Palm's batteries last longer, and it is smaller. Similarly, if you want an MP3 player, there are better, cheaper options. But if managing your contacts and having a portable MP3 player are things that you want a handheld device to do, then the iPAQ makes a lot of sense, especially if you only have so many hands.

In the rest of this article, I'll take a deeper look into many of the features of the iPAQ and the PocketPC, pointing out differences between this device and the Palm.

PocketPC Software

The PocketPC operating system is Windows CE 3.0. The development trajectory for CE has apparently followed the same curve as Microsoft Windows, requiring three versions for Microsoft to get it right. It is another example of how Microsoft utilizes the time to observe and learn from a successful competitor. Just as Microsoft learned from Apple, while Apple appeared to stop learning, so too has Microsoft learned from Palm. There must have been a lot of Microsoft engineers obsessed with understanding the strengths and weaknesses of the Palm -- more perhaps than were doing the same task at Palm Computing. It's a credit to Microsoft's persistence that if they keep working on something, they will eventually get it right.

On the whole, the PocketPC seems right. Its interface is simple and reasonably transparent. It is so integrated with the desktop that life is made very easy for a Windows user. The iPAQ shows up in Windows Explorer as a mobile device, and its contents can be browsed as easily as the contents of a CD-ROM. I can drag and drop files and the ActiveSync program will take care of any file conversion. I contrast this with several fairly rough outings trying to place a copy of a document on my Palm.

Admittedly, if you don't like Microsoft, such complete integration of the PocketPC and the desktop will only give you reason to dislike Microsoft even more. It hardly seems fair that Microsoft can make a better device by successfully leveraging its desktop dominance, along with its complete control of the Web browser, not to mention its office productivity software. That all this goes into the PocketPC package represents a significant competitive advantage in the marketplace.

Instantly up and running

I had forgotten how liberating it is to have a computer start up instantly. There is no bootup process, no waiting for the iPAQ to get going. That kind of responsiveness is what makes a handheld like the Palm or the iPAQ so enjoyable and convenient to use. It is a small amount of time, but it gets you using a computer even when you only need it for a minute or two. I found myself using the iPAQ in unexpected situations because I had a few minutes to spare.

The other side of getting up and running instantly is that you can also shut down instantly. You can also yank the iPAQ out of its cradle without having to tell any piece of software that you are going to do so. This makes it convenient to grab the iPAQ and just go.

"It is much easier to imagine and understand a more enlightened, powerful Web if we break free of some of the world's current assumptions about how we use computers. When I want to interact with a computer, I have to wait several minutes after turning it on before it is ready to converse. This is absurd. These machines are supposed to be there for us, not the other way around. So let's begin our thinking about a new world by imagining one in which a computer screen is available whenever we want it."

-Tim Berners-Lee
"Weaving the Web"


Like a Palm, the PocketPC is a pen-based computer; you tap on the screen using a stylus or your finger. Here are several things a first-time user needs to know to use the PocketPC:

The iPAQ displays a customizable Today screen as the default startup window. The Today screen lists today's calendar appointments and summarizes active tasks and e-mail messages. On the Palm, I had to buy a third-party application (TealGlance) to have the same kind of single-screen summary of important information. From the Today screen, you can choose to create new documents, contacts, or messages.

The most basic elements of the Microsoft desktop are available in modified form, whether it's the File Explorer or applications such PocketWord and PocketExcel -- or the most aptly named Pocket Money. Along with Internet Explorer, these are applications with which users are already familiar.

There are several changes that Microsoft made to the CE with the goal of simplifying the user interface. These small changes represent a departure from the Windows desktop interface. I've already mentioned that the Start Menu is at the top of screen, an important change from the previous versions of CE, which had placed it at the bottom.

The most interesting change is that you don't really close an application once you've opened it. You just move on. Applications remain open, retaining the state you left them in as you switch from one to the next. The PocketPC is supposed to intelligently manage memory allocation, closing applications (and saving data) automatically to free additional memory. Still, old habits are hard to break. During my first few hours with the iPAQ, I was looking for Exit or Quit on application menus.

There are no cascading menus and no overlaying menus, which were used in previous versions of CE but were seen to be unnecessary clutter. You won't find a File menu in PocketWord. It uses an abbreviated menu at the bottom of the screen. New is the first option on the menu, which opens a new document.

The iPAQ buttons.

The iPAQ buttons can be set for customized functions.

The iPAQ has four application buttons on the front, all of which can be customized to any function. Of the pair of buttons on the left, one opens the calendar and the other opens the contact list. The pair of buttons on the right side are Compaq-specific "Q" buttons that provide two different lists from which to launch programs. In the center of both pairs of buttons is a larger navagation button with a flower-burst pattern that conceals a speaker underneath. The navigation button operates in four directions, which is useful for browsing a list or turning pages. It also can be pressed down to act on a selected item. This button is particularly useful for Pocket Streets, which can be used to navigate a map.

InSync with Outlook

The iPAQ cradle.

The iPAQ cradle.

Bottom edge of iPAQ.

Fitting the iPAQ into the cradle can be awkward as you have to align two separate openings.

The iPAQ fits into a cradle that attaches to a desktop computer via a USB port. The cradle also has a power cord and it recharges the iPAQ's lithium polymer battery. The cradle itself is overstylized for my taste. I'd prefer something less conspicuous sitting on my desk. Fitting the iPAQ into the cradle can be awkward as you have to align two separate openings.

ActiveSync is the desktop software that establishes a connection between the desktop machine and iPAQ and then automates the synchronization process. Synchronization will occur each time ActiveSync detects a connection with the iPAQ, and if the iPAQ remains connected, synchronization will happen continuously. This means updates are recognized immediately, if you're connected.

The bulk of synchronization activity is with Microsoft Outlook, which manages the calendar, task list, contact information, notes, and e-mail. If you are already using Microsoft Outlook, then synchronizing between the desktop and the iPAQ is very easy. If not, it's fair to say that Microsoft wants you to switch. Don't expect Microsoft to make much of an effort to support competitive products such as ACT. You will have to find a third-party solution to do this, just as I had to use Pocket Mirror on the Palm to exchange data with Outlook. In general, though, Outlook is a stronger, more complete personal information management program than the Palm Desktop.

ActiveSync does not make a complete copy of all Outlook data. For instance, it is set up to download only the two most recent weeks of calendar appointments along with all future dates. This minimizes the amount of information stored on the iPAQ, but it is configurable if you need to keep more.

Screen shot of ActiveSync.

Screen shot of ActiveSync.

In many ways, ActiveSync is the same kind of program as its equivalent on the Palm. But what's more surprising about the PocketPC is the number of other ways you can move information to your iPAQ without actually using ActiveSync. If you want to move files to the iPAQ, you will find that a connected iPAQ appears as a "Mobile Device" icon in the My Computer window. You can use Windows Explorer to examine the contents of the iPAQ and drag and drop files from the desktop to the device. It's almost wholly transparent. One disappointment, however, is that the Mobile Device icon does not show up on the Windows File Menu, which means you can't save a file directly to the iPAQ.

Screen shot of Mobile Device Folder.

Screen shot of Mobile Device Folder (click to enlarge view).

You can also use Outlook to transfer selected e-mail messages to the PocketPC. This is a very useful solution. I might like to take a few important messages from my Inbox and move them to the iPAQ, but I certainly don't want all my e-mail on the iPAQ. On Outlook's Tools menu, once you've installed ActiveSync, there's a new option, "Windows CE Inbox Transfer." You can select a message in your Inbox and transfer it to the handheld device. Then you can read that message in Pocket Outlook.

When we discuss the Windows Media Player, we'll see how to move MP3 files to the iPAQ.

Infrared connections

In addition to using the cradle, you can also use the infrared port to sync up with a laptop or other computer that supports an infrared interface. I have had several computers that support infrared, and I have tried syncing up via infrared with devices such as a digital camera and a Casio organizer, but I've never had much luck getting infrared to work reliably. Until now. I was delighted that I could establish a connection between my ThinkPad and the iPAQ over an infrared connection. Given that the cradle is somewhat large and awkward to carry, it is convenient to be able to sync up via infrared when my laptop is not at my desk and connected to the cradle.

The Palm, on the other hand, does not sync up easily with a laptop via infrared, although I believe there's third party software for doing that. The Palm has become famous among users for using infrared to "beam" information back and forth, such as swapping business cards. Without having read whether it was possible, I tried to make a connection with a Palm V user. Interestingly, the iPAQ seemed to recognize the Palm device, and somehow picked up the user's name and displayed it, but we weren't able to exchange any information. The Palm V didn't respond at all.

There is software called the Peacemaker from Conduits Technologies that is designed to solve this problem. The standard edition of Peacemaker, which is free, allows you to beam and receive contact information. The professional edition, which is available for a free 30-day trial period and costs $14.95, adds the ability to beam and receive tasks, appointments, and notes. I tried this program, and while I was successful at beaming a note to a colleague's Palm V, I struggled to figure out how to send contact information. However, beaming to a Palm eventually worked using Peacemaker.

There is really no documentation on the Conduits.com site -- I'd be willing to pay for the software if there were decent documentation. The instruction to perform a soft reset of the iPAQ without further information was worrisome and had me asking the question, "Is the ability to beam a Palm user worth potentially wiping out what I have on my iPAQ?"

Writing and drawing

The PocketPC's Character Recognizer is based on Jot, developed by Communications Intelligence Corporation. How this compares to the Palm character recognition system, known as Graffiti, is a little complicated. The default input mode for the PocketPC is lowercase, which is Jot-compatible. In lowercase mode, you can select options to allow single-stroke character input. You can change to uppercase mode, which is Graffiti-compatible. Remember, these modes refer to how you draw the letters, not the resulting output. I found uppercase mode easier to use, perhaps because I've used a Palm. Even so, I found that the PocketPC character recognizer was more adept at handling certain characters such as U and V; the Palm requires a U to have a tail to distinguish it from V. On the PocketPC, in uppercase mode, you can write a U with or without a tail.

To output uppercase, lowercase, or numerical characters, you draw the character in a specific region on the screen. Writing a character in the uppercase region, regardless of which input mode you are in, will output an uppercase letter.

The most distinctive difference in PocketPC's character recognition system is how characters are traced on the screen as you draw them; this allows you to see what you've written and makes it easier to draw more complex characters and punctuation symbols.

In some applications, such as Notes, you can draw on the full screen or write in longhand. If you choose "Recognize" from the Tools menu, your handwriting will be converted into type. Obviously, results vary, but I was pleasantly surprised. I found writing meeting notes in longhand to be much easier than input via the Character Recognizer. I liked that I could use Tap and Hold to bring up a menu of alternate choices for a word that had been recognized incorrectly. (What I wrote was recognized as Tava, but it did propose Java as an alternate, which was correct.)

You can also save your handwriting as a drawing, if you choose not to convert it in Notes. You can also mix drawings, character input, and handwriting.

In addition to character recognition, you can tap away at an on-screen keyboard.

Pocket Internet Explorer

The PocketPC offers Pocket Internet Explorer and works with AvantGo to provide mobile channels from a variety of sources. This section assumes that I'm using Pocket Internet Explorer without a direct connection to the Internet, and thus I'm using the synchronization process to download information to the iPAQ that I can read using Pocket Internet Explorer.

Using Internet Explorer on the desktop, the Favorites folder has a new subfolder named "Mobile Favorites." Adding a URL to Mobile Favorites will add that URL to the Favorites folder on the PocketPC. It doesn't, however, push the content to the handheld; it's really only synchronizing the list of URLs that exist on the desktop and the PocketPC. This is appropriate if you are using Pocket Internet Explorer over a direct Internet connection, but it's fairly useless if you expect to read the content offline.

To transfer the page itself, choose "Tools/Create Mobile Favorite" in Internet Explorer and specify the update schedule for the content.

If you save a document as an HTML file in Internet Explorer on the PC and drag it to the Mobile Device folder, you'll have to use File Explorer on the PocketPC to open it. I don't see a way to open a local file from Pocket Internet Explorer.

If you want to create Mobile Channels and grab content that is often intended for use on PDAs, you will use AvantGo. You'll need to set up an AvantGo account and select which channels you want. Once you set this up to synchronize, ActiveSync will talk to the AvantGo site and update content from these channels on your iPAQ. I set it up initially to fetch the daily New York Times headlines, Boston Globe sports, Salon, and The Economist. These channels are listed on the home page of the Pocket Internet Explorer. You can also add your own channels in the AvantGo service, but this content will not be specially formatted for a handheld.

In general, AvantGo works the same way on the Palm. The Pocket Internet Explorer is able to display richer content (color, frames, tables), but you are still dealing with a 240 x 320 screen region, which most pages are not designed for.

Microsoft Reader

As a publisher, I've had a personal interest in the development of the Microsoft Reader, software designed to make it easier to read books online. I was curious about how Microsoft Reader worked on this platform, and how it compared to the special reading devices such as the Rocketbook, which have not done so well in the market.

What I like most about the Microsoft Reader is its simplicity. Its interface is satisfyingly book-like, and it is not cluttered with menus and buttons the way that the Acrobat Reader is. There are a few "classic" texts available free for download or on the ActiveSync CD that allow you to test out the reader. There is also a "Pocket" version of the Encarta Dictionary. When it's installed, you can easily look up a word in any ebook, by selecting the word and using Tap and Hold to bring up a menu with the Lookup option.

When you find a ebook that you want to read on the iPAQ, you can simply drag and drop it into the Mobile Device folder or one of its subfolders.

I have spent several hours reading "Great Expectations" with Microsoft Reader and using Internet Explorer to read New York Times headlines. The difference between the two is the use of ClearType font technology in the Reader, which I'm not too clear about. In some ways, it improves readability. But the type is also a little fuzzy. The Reader does provide a fairly consistent interface for turning pages, and there are no ads! I have enjoyed the time I've spent reading on the iPAQ. I am familiar with arguments that people don't like to read on such devices. However, it may not be fair to compare ebooks straight up to print books. What I've found valuable is that if I have my iPAQ, I have some reading material always with me. Once recently, I had to wait ten minutes or so in the car for my son's football practice to finish. I wouldn't have thought to bring a book or magazine with me, but I had the iPAQ and I was grateful to be able to occupy myself by reading

Download The Jargon File by Eric S. Raymond and Guy L. Steele.

The 1.0 version of Microsoft Reader shipped with the PocketPC. Since then, Microsoft has made the reader available for desktop PCs. I downloaded it recently and bought an ebook at Barnes and Nobles. Unfortunately, the PC Reader is version 1.5, which supports Digital Rights Management. Since this is missing in the 1.0 version, you won't be able to read ebooks on the iPAQ that have been encrypted for sale. Microsoft is working on an update for the Reader, which is due later this year. Amazon recently announced that they will also begin selling ebooks that support the Microsoft Reader format.

I experimented with some tools for producing ebooks. Overdrive's Readerworks (www.readerworks.com) provides both free and professional versions of tools that will read HTML files and generate a Microsoft Reader-compatible book. The Microsoft Reader supports the Open-ebook standard, which is based on XHTML and CSS, although those files must be processed into an internal proprietary format (.lit) for distribution.

Windows Media Player

The Windows Media Player (WMP) allows the iPAQ to function as a portable audio player. It plays MP3 files and also supports a Microsoft format known as WMA. This format uses a different compression codec and generates a smaller file size than MP3.

Once you start the Media Player, it will continue to play in the background even if you go on to use other applications. Windows Media Manager for the PocketPC is available on the ActiveSync CD in the Extras folder; it can also be downloaded from Microsoft.

Screen shot of Windows Media Manager

Screen shot of Windows Media Manager (click to enlarge).

I began with several MP3 files which we produce for the Open Source Audio Roundtable. I successfully moved a 1.9 MB file to the iPAQ, and the Windows Media Player successfully played it. I moved two larger MP3 files (6.5 MB and 9.2MB) to the iPAQ but, while they were recognized as MP3 files, the player would not play them. I converted one of the files to the WMA format, reducing the 9.2 MB file to 4.6 MB in size, and it played well. My supposition is that there are undocumented restrictions on either file size or encoding formats for the Windows Media Player on the PocketPC. Nonetheless, the WMA format achieved a significant reduction in file size for these recorded conversations.

I downloaded the Windows Media Player 7.0, which is also an encoder. I was pleased to see a button labeled "Portable Device." That opens a view of the MP3 or WMA files on the iPAQ, and provides the ability to copy files from the PC or from the CD to the iPAQ. Anyone who has struggled with the Rio's software will be happy to see the integration of downloading files from the Internet or ripping files from a CD and moving them to a portable player all integrated in one software interface.

Space is limited on the iPAQ, once you have added your programs and such. To carry around a lot of MP3 files will not be practical without buying the CompactFlash adapter. The advantage of CompactFlash is that you can store files on a CompactFlash card and swap in cards with different playlists. (My experience with the Rio suggests that because it took a fair amount of time to download files to the device, I wasn't going to do that often. It meant I listened to the same six or seven songs repeatedly.)


iPAQ record button.

The thumb button for recording.

The iPAQ has a built-in microphone and a thumb button on the left side that can be used to start and stop recording. It's intended for short recordings such as notes and annotations.

The default settings for recording produced fairly poor results: low volume and crackly. There's an option for Microphone AGC (Automatic Gain Control); the option itself is a little hard to find. AGC is enabled by default but I got better sound quality by disabling it.


The PictureViewer application allows you to look at jpeg images. It's a good reason to get others eyeing this bright color iPAQ screen. I can see carrying a few family photos and such on the iPAQ.

If the image is too large for the screen, then you can pan and scan to see a portion at a time.

Because the iPAQ can be extended to use CompactFlash cards, and a number of digital cameras support CompactFlash, PictureViewer may provide yet another way to examine or present a personal photo collection.


I've ordered some of the accessories but they haven't arrived yet. So I don't have any firsthand experience.

The two main reasons for expanding the iPAQ are to increase the amount of storage available by adding CompactFlash cards or to make a connection using a modem or Ethernet card.

The iPAQ is expanded by buying a separate wrap-around sleeve that serves as a holder for CompactFlash cards. There is also a separate sleeve holder for PCMCIA cards. (The sleeve that ships with the iPAQ improves the grip when holding the iPAQ but otherwise has no functional purpose.) I look forward to seeing if a wireless PCMCIA card will allow me to connect the iPAQ directly to our wireless LAN.


For a detailed comparison of the color Palm IIIc and the PocketPC, see "There's a War Going on In Our Pants! (the Palm OS vs. Pocket PC)" written by the staff of Semper Aptus. See the head-to-head chart. The authors make a good point in that the monochrome Palm is faster and more efficient with a slower processor and longer battery life. It is designed to do less. Adding color adds complexity and saps power more quickly.

The PocketPC and the Palm

I know the Palm is designed to be just a PIM. But developers have been doing the most amazing things with the Palm to broaden its capabilities. A recent Harper's Index reported that a Starbucks locator is the most popular Palm application. (I haven't been able to track down the source for that stat; if you've come across it, let me know.)

As a platform, the Palm is perceived as extensible and open, a belief that has helped to create an active developer community. Palm's greatest asset may not be its hardware but this developer community. Perhaps the Palm as a device has not kept up with the developers who are extending it. The Palm needs to find a way to move beyond its original focus as a PIM. Otherwise it risks being upstaged by more capable, user-friendly devices such as the PocketPC.

Dale Dougherty is the editor and publisher of MAKE, and general manager of the Maker Media division of O'Reilly Media, Inc.

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