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BlackBerry Wins Versus Windows Mobile For Google Apps Mail

After a flawed experience with one of the first Windows Mobile-based Motorola Q's, Microsoft outfitted me with a Samsung SCH-i760 smartphone which, from an industrial design perspective, is one of the best designs for a smartphone I've ever experienced (more on that in a second). Unfortunately, integrating WinMobile 6.0's version of Outlook with Google Apps-based Gmail was so problematic that I gave up in favor of a company-furnished BlackBerry. BlackBerrys are rumored to work well with Gmail. But is that really the case and why doesn't stuff like this just work? It's an interop nightmare.

Ideally, when you integrate your mobile device with your e-mail, it shouldn't be too much to ask to keep your folders in sync between the two. The same goes for the "state" of each e-mail item. For example, if I open an e-mail with my mobile device without deleting it, it should appear as though it we're opened when I look at it on my PC (and vice versa).

Likewise, I should be able to delete a mail on the e-mail client of my choice (Mobile Outlook or otherwise) using the client's method for deleting mail and everything should behave predictably. With Mobile Outlook and Gmail using the IMAP protocol (the only of the mail access protocols that supports folder synchronization), I can't use Mobile Outlook's delete command because that moves it to a folder called "Deleted Items." IMAP-based synchronization then forces the replication of that folder over on the Gmail side of things and unfortunately, Gmail's deleted mail folder is named something completely different: "Trash".

To me, interoperability problems like these are tolerable. I just worked around them. But most people would never put up with this sort of crap. It should just work (and work well for both e-mail and calendaring). But, what really got under my skin was the parade of error messages from Mobile Outlook that synchronization had failed and that I should check the settings to make sure I have them set correctly. Sometimes, it worked famously well. Other times, it would fail miserably, leaving a dialog box on the screen that would lock Mobile Outlook up until I manually cleared it (it should clear itself after some amount of time and simply retry).

I gave up. Windows Mobile, it was good to know ya.

Though it's the best thing going and Gmail is one of the few online e-mail services that supports it, IMAP is, for all intents and purposes, a busted protocol and there isn't much that Google or the various e-mail client providers (mobile or desktop) have done to overcome its weaknesses. Maybe the new version of Mobile Outlook on the newer smartphones (like the new Treo) works better. I kind of doubt it since the latest version of Windows Mobile isn't Windows Mobile 7 (due in 2009).

My sense now is that nothing mobile (BlackBerry included) will ever work as well with a Google Apps-based Gmail account as Google's forthcoming Android mobile OS probably will. Yes, I've heard the iPhone is worth looking into. If only AT&T offered a consistently good signal in my house. It doesn't. One important sidebar: when certain mobile devices work better with certain back-end services (e.g.: Windows Mobile with Exchange, Android with Gmail, iPhones with iTunes, etc.) and some of those choices end up aligned with specific mobile operators the way the iPhone is aligned with AT&T, it's a very bad sign that silos and walled gardens are forming. I'm praying the economic forces of openness will reign supreme. But it's not looking good.

All this said, I do have one thing to say about Samsung's SCH-i760 smartphone. With a regular phone keypad on top and a slide-away QWERTY keyboard underneath, the numeric keypad stays active when going into QWERTY mode so that I don't have to engage any FN or modifier keys to type numbers. I just move my fingers from the QWERTY keyboard to the numeric keyboard and back again. The design is brilliant and I'll be sorry to see that go.

BlackBerrys -- even the ones with the full QWERTY keyboard -- require you to press a key modifier button to switch certain buttons from letter to number mode. Thankfully, the BlackBerry often (not all times) intuits when it should automatically modify those keys (like when entering a phone number). Windows Mobile rarely did this (actually, this sort of keyboard intuition has always been one of the BlackBerry's most endearing features to me).

When my company-furnished BlackBerry 8700c arrived, the first thing I did was load it with a Gmail client that Google makes especially for the BlackBerry. I was very excited and looking forward to perfect interoperability. But I was crushed to find out that it only works with standard Gmail accounts and not Google Apps-based Gmail accounts. For Google Apps-based Gmail accounts, Google recommends using the mobile Web interface which isn't (and may never be) nearly as robust what an actual e-mail client can do (especially in a mobile browsing situation).

Unfortunately (because of the signal issues), all company-furnished phones are provisioned by AT&T (*sigh*). But fortunately, AT&T runs what I'm guessing is the equivalent of a BlackBerry Enterprise Server (BES) and it can be pointed at any online e-mail service, including the Google Apps version of Gmail.

A BES server is what many companies use to keep their users' BlackBerrys perfectly in synch with Microsoft Exchange or Lotus Notes e-mail and calendaring servers. For mobile operators, their BES (or BES-equivalent) does the same with the popular e-mail services like Yahoo and Gmail. In fact, whereas Gmail is very picky about how it is accessed by e-mail clients, requiring manual resetting of ports and such, I was simply amazed at how AT&T's Web site asked for nothing more than the address of the inbox I wanted to keep in sync and the password for the inbox. AT&T took care of the rest.

Well, almost.

Copies of certain e-mails that I draft are unpredictably replicated to my BlackBerry as though some of the contents (not all) in Gmail's Sent Mail folder belong in the Inbox on the BlackBerry side of things. At first, this was happening with all sent mail until I configured the BlackBerry to not include Sent Mail. But some of my Sent Mail still squeaks through and I haven't figured out why. Also, the "Opened" and "Unopened" states of my e-mail aren't correctly synced and I'm not sure why that is, either. But, overall, the situation is significantly better than it was on Windows Mobile 6.

If you've had a nightmare or total success being your own personal mobile integrator (or, you think I overlooked something in my criticisms), then please share your story with me and other InformationWeek readers by using the comments section below.

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