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Old 09-14-2005, 07:00 PM
Jason Dunn
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Join Date: Aug 2006
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Default Picking the Right Email Strategy for Your Windows Mobile Device

Windows Mobile-based devices, both Pocket PCs and Smartphones, can be powerful tools for working with e-mail. If you're anything like me, you get a lot of e-mail every day, and managing the flow of e-mail when you're away from your desk is a critical task best accomplished with a Windows Mobile-based device. There are several options for working with your e-mail, including POP, IMAP, and Exchange ActiveSync. Each has specific advantages and disadvantages.

If your company only offers one option, this article may not be of much use to you�it's primarily geared for mobile workers who have the freedom to decide which of the three options works best for their needs. This article assumes you use some version of Outlook and a wireless connection to access the Internet from your device. Let's take a look at e-mail options, and when you might use each one.

POP/POP3 E-mail Accounts
POP stands for Post Office Protocol, and it's been around for a very long time. POP2 became a standard in the mid-'80s, but POP3 is the version most of us are familiar with, and it's still in use today. A history of POP can be found at the Wikipedia site. Today, if something refers to POP, it's really POP3. Microsoft Office Outlook Mobile supports POP, and odds are that if you have an e-mail account, it's going to be POP by default. Most Internet Service Providers (ISPs) offer POP e-mail accounts, and if you get set up with a Web hosting account you'll undoubtedly be able to use POP as an option. This doesn't apply to Web-based e-mail accounts such as Hotmail.

POP accounts in Outlook Mobile work fairly simply�clicking the Send & Receive button is all it takes�but they're also limited in functionality. When you check your e-mail, it's downloaded to your mobile device and a copy is left on the server. This cannot be changed. If you delete a message from your inbox, it will disappear from view on the mobile device, but it will still be on your desktop computer when you connect with your e-mail client. This can be avoided by emptying the Deleted Items folder on the device or by configuring Outlook Mobile to delete items immediately, but it's a bit of a hassle. Another limitation of POP is that it can't support multiple folders. Everything has to stay in your inbox folder, and you can't move e-mail to other folders on the server for archiving.

Although most e-mail clients (including Outlook) can be configured to leave messages on the server for x number of days, the vast majority of people using POP pull down e-mail to their local computer and delete it from the server. The net result is that all your e-mail is on your main computer in a single Outlook PST file, and only new messages are accessible on your Windows Mobile-based device. This means you have to protect that PST file from data loss.

POP e-mail really breaks down as a solution when you introduce a laptop alongside your desktop computer and try to keep your e-mail in sync between the two. For years I tried to do just that. I tried a variety of file synchronization tools to push my 2 GB PST file from laptop to desktop and back again, but they were all clumsy and slow. I purchased Outlook PST synchronization tools to keep the two PST files in sync, and suffered through all manner of bugs, crashes, and lost data. Outlook was simply not designed to be used in this way, and it shows.

If you have a single desktop or laptop computer and one mobile device, POP3 is a decent choice because it's simple to use. If you have the option, however, IMAP is a better overall choice. Read on to find out why.

IMAP/IMAP4 E-mail Accounts
IMAP, also known as the Internet Message Access Protocol, was designed by Mark Crispin in 1986. It's similar to POP in that it's a widely supported protocol, usable in Outlook and in Outlook Mobile on Windows Mobile-based devices. IMAP isn't as widely supported as POP, largely because it requires more server resources to support. Most ISPs do not offer IMAP as an option, but most Web hosting packages that include e-mail hosting will offer IMAP alongside POP. In fact, many e-mail accounts nowadays can be accessed via POP or IMAP, depending on how you configure your e-mail client. It's best to stick to one method rather than mixing them. IMAP is an improvement upon POP in many ways, but the core advantage is that all your e-mail remains on the server. If using POP results in all your e-mail being collected and held on the local computer in an Outlook PST file, IMAP is the opposite�all the e-mail stays up on the e-mail server. Copies are downloaded to your local computer and cached for offline use, but the server is where all your e-mail really lives. Another key advantage is that IMAP supports sub-folders, meaning you can sort and archive your e-mail, all on the server.

The advantages of this are immediately obvious when you configure Outlook on your desktop and Outlook Mobile on your mobile device so that you can access e-mail via IMAP�both devices show all the available folders, and download the e-mail you specify. The power of this solution can't be overstated. Whenever I set up a new computer or Windows Mobile-based device, I enter in my IMAP e-mail account settings. Within seconds I have access to all my e-mail, even though it's spread over dozens of folders. On a Pocket PC I can select Tools > Manage Folders and see all of my e-mail folders. By checking off the box next to the folder I want, I can download all the e-mail in that folder. This can be extremely useful if you need to access old e-mail sitting up on the server.

IMAP is not without its limitations�most IMAP accounts can only be accessed by one e-mail client at a time, so if you leave Outlook open at work and access your e-mail from a Windows Mobile-based device it may connect, then disconnect and give you an error statement about the account already being in use. And IMAP works only for e-mail, so it can't keep your Contacts, Calendar, and other Outlook data in sync.

There's also some peculiar behavior with Outlook Mobile and IMAP. When you switch to an IMAP account with Outlook on the desktop, it immediately connects and downloads all new e-mail as it should. It stays connected until you exit from Outlook, and any changes you make (moves, deletions, etc.) are tracked because you're connected to the server. However, Outlook Mobile doesn't automatically connect when you switch to the IMAP account. You'd think that tapping Send & Receive would be the right thing to do since that's what you do with POP e-mail accounts, but it's not: if you do a Send & Receive, Outlook Mobile will connect, grab your new e-mail, and then disconnect. Any moves or deletions you make will not be reflected on the server until you do another Send & Receive�and sometimes it doesn't work properly, resulting in duplicated and un-deleted e-mail when you start up Outlook or connect the mobile device to your e-mail account again.

Avoid this by tapping the Connect button when you want to check your IMAP account. Then you interact with your e-mail (read it, delete it, etc.), tap Send & Receive once, then tap Connect again to disconnect. Also, if you're connected to large folders Outlook Mobile sometimes disconnects randomly from IMAP. You need to watch the Connect icon and ensure you're always connected when making changes. Lastly, with IMAP folders containing hundreds of e-mail messages it will often re-download the same messages each time you connect. Based on my experience, IMAP works best on Windows Mobile-based devices when there are less than 200 messages in the folders you're synchronizing.

IMAP is a great solution if you want to access e-mail from more than one computer�for instance, a desktop and a laptop. I access my e-mail accounts from two desktop computers, three laptop computers, and two Windows Mobile-based devices, all using IMAP. It's less reliable on the mobile devices, and since it doesn't support Outlook data synchronization such as Calendar and Contacts, you still need to synchronize your mobile device with just one of your desktop or laptop computers. Now that ActiveSync 4.0 no longer supports wireless synchronization with a desktop computer, this means physically connecting your Windows Mobile-based device each time you want to sync�unless you're doing an Exchange ActiveSync, which is my preferred solution.

Exchange ActiveSync
Microsoft Exchange 4.0 was first introduced as Exchange Server 4.0 in 1996 as a corporate e-mail tool. It's evolved over the years to be a collaborative software server. The current version is Exchange Server 2003, and Service Pack 2 coming out later this year will add some compelling features, most notably Direct Push Technology e-mail support that puts Windows Mobile-based devices on a par with instant-messaging devices. Until fairly recently, Exchange accounts were the purview of employees of large corporations and something that most small business owners lacked. Many of the wireless synchronization features introduced in past versions of Windows Mobile required an Exchange account, so I felt left out until I discovered the marvels of a hosted Exchange account.

What's hosted Exchange? First, let's consider all the things you'd need to have in order to have your own Exchange account: a server, the license for Exchange, a special Internet access account (most ISPs ban people from running any type of server on consumer-level Internet access accounts)�and the knowledge and skill to install, configure, and keep an Exchange server up and secure. I tried setting up an Exchange server once, and simply didn't have the necessary knowledge to get it working properly. I must not be the only one who had trouble, because there are hundreds of companies out there that take the headache out of running an Exchange server. For a monthly fee, they manage the server, the configuration, and all the security. You simply synchronize with your server, and that's it. You get all the benefits with none of the hassle�that's my kind of solution!

I've tried two services over the past two years, and settled on a company named 4Smartphone in late 2004. Don't let that name fool you, their service works with both Pocket PCs and Smartphones. Their $6.99/month plan gives you both Windows Mobile and desktop Outlook synchronization and 1 gigabyte of space on their server for your e-mail and Outlook data. If you don't need to synchronize Outlook, for $3.99 a month you can get Windows Mobile-based device synchronization and Outlook Web Access (OWA). There are many other companies with hosted Exchange offerings, so pick the best one for your needs: an MSN Search query for the terms "hosted exchange" turns up some 103,000+ results.

Exchange really shines in multiple-device scenarios. I use several computers day-to-day, and having up-to-date information on all of them is critical. By having all of my e-mail and Outlook data (Calendar, Contacts, etc.) sitting on the Exchange server, I can keep all my devices in sync painlessly. If I'm working on my desktop computer and make changes to my calendar and contacts, then leave my office carrying only my Smartphone, I know that within a few minutes all those changes will be on my Smartphone. The side effect of this is that your Outlook data is protected from loss because it's on multiple devices. Having once lost a 2 GB PST file full of data, it's a comfort knowing my data is mirrored on five different computers and two different mobile devices.

Exchange and Outlook 2003 also have a fantastic offline cached mode. When Outlook 2003 is offline you can move, delete, read, respond, and change any piece of Outlook data�unlike IMAP where you need to be connected live to the server to really do anything. The next time you connect, all those changes are uploaded to the Exchange server and then mirrored when you connect your other devices.

Windows Mobile-based devices can be configured to synchronize on a time basis (i.e., every thirty minutes), or when new items arrive. That means when a new item arrives (say, a new e-mail message), the Exchange 2003 server sends an SMS message to your mobile device. That SMS message contains the command to start up an ActiveSync session on the device, which then connects to the Exchange account and pulls down the new e-mail. With the forthcoming Windows Mobile 5 devices, and the SP2 update for Exchange 2003, the scenario will get even easier: when a new e-mail arrives on the Exchange server, it's immediately pushed down to the device, just as with other instant messaging devices on the market.

The setup of a hosted Exchange is also amazingly simple�4Smartphone offers me a setup file that I can download. Once I double-click the file and enter my username/password, Outlook 2003 is automatically configured and all e-mail and personal data starts to download immediately. Outlook 2003 is required if you don't want to mess with VPN configuration, but most hosted Exchange providers give users a free copy of Outlook 2003 with the setup of their account.

As great as a hosted Exchange account is, there are still some baffling limitations. There's no way to sync Tasks as of yet (this is fixed in the upcoming Exchange SP2 release, but you need a Windows Mobile 5 device for it to work), no way to sync Notes, and no synchronization of documents or favorites. I'm hoping that future versions of Windows Mobile and Exchange Server will offer more options.

Despite these limitations, using a hosted Exchange account is one of the best technology decisions I've ever made. It allows me to use multiple devices, yet always be in sync and up to date. The freedom of not having to worry about whether or not a particular device is up to date is priceless, and has made my devices much more useful to me.

Windows Mobile-based devices make ideal tools for managing your e-mail�whether it's deleting spam so you'll come in to a clean Inbox at work, triaging and forwarding important messages while you're out of the office, or sitting down with a folding keyboard at the airport to really dive into all that e-mail. Once you start using your Windows Mobile-based device for e-mail it will become even more valuable to you.

It's important to understand that you can use these three options in tandem. Windows Mobile-based devices support up to eight e-mail accounts in Outlook Mobile, so you can have a POP e-mail account, an IMAP account, and a hosted Exchange account. In my case, I use my 4Smartphone-hosted Exchange account for my primary work e-mail, and four IMAP accounts�one for my personal e-mail, and one for each of my Web sites. You might use a POP e-mail account for personal e-mail.

In an upcoming article we'll tackle setting up a Pocket PC and Smartphone with an Exchange server, and what sort of issues and options you'll have.
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