I've been a faithful user of Research in Motion's (RIM's) BlackBerry for many years and have enjoyed the fast and reliable email access that BlackBerry provides. When Microsoft introduced the upgraded Mobile Services in Exchange Server 2003 Service Pack 2 (SP2) and Windows Mobile 5.0 became available for a new range of Pocket PC hardware, I decided to investigate whether I should switch my loyalty. I've used both a Windows Mobile 5.0 handheld and a Windows smart phone as my primary messaging device. As you'll see, I found some notable differences between the Windows Mobile/Pocket PC and BlackBerry devices in how they perform messaging tasks and in some other areas as well.

Making the Switch
I moved from the BlackBerry to the Pocket PC by taking my Subscriber Identity Module (SIM)—the identification card that links your phone number to a network—out of the BlackBerry, inserting it into the Pocket PC, and powering up the device. Cell phone providers usually issue devices that are locked to specific networks, so it might not be possible to simply move your SIM if the device that you want to transfer your SIM to belongs to a different provider. Apart from the data held on the SIM (usually just contact information), you can't copy information from one device to another; you have to resynchronize with Exchange to download your email, calendar, and mailbox contacts to the device.

Before I moved over to the Pocket PC, I enabled my mailbox for mobile access, which you can do only as an administrator. On an Exchange 2003 server, you enable mailboxes to use Mobile Services by editing the user account's properties through the Microsoft Management Console (MMC) Active Directory Users and Computers snap-in, which Figure 1 shows. On Exchange Server 2007, you access mailbox properties through Exchange Management Console and you enable Exchange ActiveSync (EAS) from the Mailbox Features property page. Of course, Exchange 2007 supports PowerShell scripting through Exchange Management Shell, so I could have enabled my account with the Set-CASmailbox command, like this:

Set-CASMailbox -id Redmond
   -ActiveSyncEnabled $True

I also ensured that I knew the name of the Microsoft Internet Security and Acceleration (ISA) Server machine to which the Pocket PC would connect, so that my device could connect to my company's network and synchronize my mailbox. Finally, I installed the latest version of Microsoft ActiveSync onto my PC; the PC version of ActiveSync is required if you want to download software onto your PC, then transfer it to the Pocket PC. It's also easier to set up synchronization between the handheld and Exchange using ActiveSync on the PC.

Getting Email
Processing email is similar on Windows Mobile devices and BlackBerries. Windows Mobile devices provide a more graphical UI; BlackBerry users tend more extensively to use keyboard commands to navigate their Inbox, calendar, and other applications. Both types of handheld fetch the complete content of small messages and the first portion of larger messages; you can instruct the device to fetch the complete content and attachments if you want to read everything on the handheld.

I use a default message-download size of 5KB for my Windows Mobile device, which works well for almost all messages, even those that are part of a long email thread. I also changed the default time window for message storage from three days to one week to ensure that Microsoft Pocket Outlook held more of my Inbox on the device. These settings, which you can make through ActiveSync on the PC or the handheld, affect the amount of storage used on the handheld. You might need to add more storage to the device if you want to hold a lot of data locally. Windows Mobile lets you store attachments on a miniSD card, which allows more storage for messages.

On Windows Mobile devices, you can use Pocket Outlook to view the complete folder structure of your mailbox and select folders for synchronization to the handheld, as Figure 2 shows. Thereafter, Pocket Outlook will synchronize new items that appear in these folders, but it won't synchronize items already in the folders. Being able to synchronize selected folders to your handheld is an advantage for Pocket Outlook.

Both clients let you download attachments. BlackBerry Enterprise Server for Microsoft Exchange (BES) converts common document formats such as Microsoft Word and Microsoft Excel to a format that BlackBerries can read. Pocket Outlook doesn't have to convert common Microsoft Office formats because Windows Mobile includes versions of Word, Excel, and Microsoft PowerPoint. The BlackBerry fetches document contents as you request them; Pocket Outlook waits for the next synchronization cycle. You can also start synchronization manually through ActiveSync or Pocket Outlook; this is useful if you want to control roaming or data costs when you're away from your home network.

The BlackBerry supports a directory lookup against your contacts and against the Global Address List (GAL). The lookup feature completes a search of some 300,000 objects in less than five seconds. Windows Mobile includes a feature that provides similar functionality, as Figure 3 shows. Pocket Outlook often matched the BlackBerry in directory-lookup speed but occasionally took up to 30 seconds to perform a search.

The speed of message delivery to the handheld is similar for BlackBerry and Pocket PC, although the underlying infrastructure that you deploy to support mobile users influences delivery times because delivery speed depends on factors such as load placed on the servers and complexity of network connections. EAS groups messages for transmission to the Pocket PC, sending new messages only during synchronization rather than as they arrive in the Inbox. The BlackBerry processes new messages as they arrive, which puts a much bigger load on an Exchange server because it polls mailboxes constantly to discover new email, then extracts and transfers messages to the handhelds.

Other Messaging Options
Exchange-based messaging is important for the enterprise world, but Short Message Service (SMS) is also important, particularly for personal communication. BlackBerry's integration of SMS is better than Windows Mobile's because it treats SMS messages as just another message type and incorporates them into the BlackBerry's Inbox. Pocket Outlook stores SMS messages in a separate Inbox and outbox. Windows Mobile displays text from incoming SMS messages as a notification at the bottom of the screen. You tap the notification to see the complete message. If you want to send an SMS message, you have to select a contact, then opt to send an SMS message; it would be easier if the steps were more integrated.

You can use either handheld as your single communications device. However, if you want to use it as a phone, you'll probably find that a Windows smart phone is more like a standard cell phone.

Power Management
Even with heavy email use and a fair amount of phone use, my two-year-old BlackBerry lasts up to two full days and sometimes three without needing a charge. Because the capacity of a rechargeable battery to hold a charge degrades over time, the ability of such an old device to provide extended service is very good. By comparison, a Windows Mobile device is usually hungrier for power and exhausts its battery faster than a BlackBerry does. You can expect up to two days' use on the Pocket PC if you're careful to conserve battery use. Phone calls are the quickest way to drain the battery, but using features such as Windows Media Player (WMP) also drain power fast. Windows smart phones have a much longer battery life than Pocket PC devices and comfortably match the BlackBerry in this respect, even if they don't get close to the 14-day capacity boasted by some regular cell phones. You can recharge BlackBerries, Pocket PCs, and smart phones by connecting them via USB to your PC or possibly through an optional AC adapter.

On versions prior to Windows Mobile 5.0, you didn't want a Pocket PC's battery to run out because you'd lose customized settings and have to resynchronize data after you recharged the device. Windows Mobile 5.0 stores user settings and data in solid-state memory so they aren't lost even if the device completely loses power. The BlackBerry has traditionally been more resilient to power failure and doesn't require you to make as many tweaks after a recharge.

Input Flexibility
The BlackBerry 7100 marked a big change from the traditional BlackBerry keyboard because multiple letters are assigned to keys. However, the predictive recognition software does a good job of figuring out which letter you mean. You do everything on a BlackBerry through the keyboard or by navigating command menus with the thumbwheel.

Windows Mobile devices typically have more keys for individual characters and support a software keyboard, voice recording, block character recognition, and handwriting recognition. Windows Mobile also provides keyboard shortcuts, but you still need the supplied stylus or a pen (or a finger, after you lose the stylus) to get work done. Windows smart phones use the 12-key layout of standard cell phones, so it's more challenging to compose messages on them. After you get used to the predictive text engine, you can compose reasonably complex messages, but a device with an integrated full keyboard will always be better for answering email.

The version of Microsoft Internet Explorer (IE) supplied on the Windows Mobile platform is a real strength; I've used it to do things such as discover what time to catch a bus in Paris, find a hotel or restaurant phone number, check airline schedules, and more.

BlackBerry is a fast, straightforward, and powerful email client, but when you want to do more than email, you start to hit limitations not found on Windows Mobile devices. The BlackBerry uses a less-graphical interface than the Pocket PC and smart phone; the BlackBerry browser struggles with all but the simplest Web page. You can receive attachments on the BlackBerry, which BES interprets, but the native Office compatibility built into Windows Mobile does a far better job of displaying Office documents, as Figure 4 shows.

Trading Addictions?
For most of us, it takes time to get used to something new. As an experienced BlackBerry user, I had grown accustomed to a certain way of doing things. It took me time to figure out how everything worked on the Pocket PC, but the combination of the device, Windows Mobile 5.0, and Exchange 2003 SP2 convinced me that I could survive withdrawal pains and make the transition away from my BlackBerry. Windows Mobile gets even better with the next version, codenamed Crossbow, and the new devices that support Crossbow, especially when they work with the upgraded ActiveSync in Exchange 2007. The growing maturity of the Windows Mobile platform and the devices that it supports means that RIM has to innovate at an increasing rate to keep up—and that's good news for users.