This shouldn't be surprising, but by mimicking its success with desktop versions of Windows in Windows Mobile, Microsoft has created a mobile OS that has many of the same strengths and weaknesses of its inspiration. Equally unsurprising, then, is the fact that Windows Mobile's greatest strength--the diversity of devices on which you can acquire the new system--is also its greatest weakness.

The solution to this problem should be simple, but it isn't. When Microsoft opted, at great expense both financially and to its credibility, to launch the Zune platform and undermine its years-old hardware, software, and services partnerships as a result, the company didn't exactly reap great success. In fact, if anything, Zune devices have accounted for a smaller share of that market each year since the platform has launched.

While the similarities between the MP3 player market and smart phone market should be obvious, I will also point out one big difference: The smart phone market is dominated by wireless carriers that largely determine which devices are put in front of customers. So there's an additional level of micromanagement occurring there, and another master for everyone to please. And outside of Apple, virtually all major league smart phone makers thus make specialty devices to appease each wireless carrier. So you'll see different Blackberries on AT&T, T-Mobile, and Verizon Wireless, each customized according to the whims of the various carriers.

Windows Mobile benefits from--and suffers from--this same issue. And while some may claim that this increases choice, the reality is that unless you happen to be in a timing sweet spot where it's inexpensive or free to actually switch carriers, you're really limited to the few devices that happen to be sold by the carrier you're stuck with. Literally, in my case. As an iPhone user, I'm stuck with AT&T.

You could search forever before you'd find someone credible willing to defend AT&T. (And one recent high-profile story in The New York Times doesn't count: That was clearly a BS attempt to drive readers to a story that everyone knows is untrue.) But this isn't about AT&T: When it comes to choice, the wireless carriers are all lousy. (And to be fair to AT&T, they do actually have excellent customer service, for whatever that's worth.)

Looking at Windows Mobile 6.5 in particular, here's how it breaks down as I write this. AT&T offers three devices, each of which has a different form factor. There's the HTC Tilt 2, which I'm currently testing, which features a pull-out hardware keyboard. Then there's a touch-only HTC PURE and a Blackberry-style iPAQ Glisten (with a small, hardware-based thumbpad). Sprint has a single device.T-Mobile? None. And Verizon has two, an HTC Imagio (basically their PURE) and a Samsung Omni II which, curiously, is touchscreen only, just like the Imagio.

So your choice isn't as great as you were led to believe. It's even worse when you consider that Microsoft (and thus Microsoft's partners) is actually selling two different versions of Windows Mobile 6.5, Standard and Professional. Speaking simply, devices with very small (320 x 240) screens typically (but not always) run Standard, which lacks virtually all the important new UI stuff that makes Windows Mobile 6.5 at least somewhat interesting. The Professional devices, however, include the touch screen capabilities, the new user interface, and so on. You really want to get the Professional version if you can.

There is a third route for Windows Mobile phones, of course, as there are for all smart phones. You can simply buy an unlocked phone, at great expense ($500-$600 oftentimes), from an online retailer like Expansys. When you do so, however, you have to be careful to buy the right type of device, since the wireless market in the US is currently split between CDMA (Sprint, Verizon) and GSM (AT&T, T-Mobile) type networks. The two are not compatible with each other, though GSM is pretty much the international standard. (Some CDMA phones, called "world phones," are sold with two antennas so you can use them in the US and internationally, though often at great cost.)

In November, I purchased an unlocked Acer smart phone from Expansys. And I'm currently testing an HTC Tilt 2 loaner device, courtesy of Microsoft. I do happen to be stuck on the AT&T wireless network right now--thanks, iPhone--so this limits my choices to what AT&T offers, or, if I feel like spending a lot of money upfront, whatever unlocked GSM devices are out there.

Both devices run Windows Mobile 6.5 Professional. The Acer is a touchscreen device, like the HTC PURE, and the HTC Tilt 2 is a thicker design with a large pull-out hardware keyboard. But both devices share a common design element, and it's one that places them well behind the iPhone from a usability perspective. That is, instead of incorporating a capacitive touch screen, as does the iPhone (and Verizon DROID and Palm Pre), all touch-based Windows Mobile 6.5 devices currently do not. These devices utilize a non-capacitive design that is harder to press and results in numerous mis-touches, where you actually intend to scroll through a list of icons (typically) but then it registers a touch/tap and launches whatever application or utility you happen to be trying to scroll past.

It's annoying, and while it does happen less frequently as time goes by and you become accustomed to the screen, it never actually goes away. This has such a negative impact on the user experience that I'd be surprised if many users didn't return these phones solely for this reason. Non-capacitive screens are so lousy, so unfriendly, that I simply must recommend that if you are going to get a Windows Mobile 6.5 phone, you should wait until a device with a capacitive screen appears. (The first, the HTC HD2, will soon ship from T-Mobile, and others are coming in the first half of 2010.)

[ Read more about Microsoft's plan to improve Windows Mobile this year. ]

And that means... Right. You should not be buying a Windows Mobile 6.5 phone right now. Period.

Well, there is one exception. If you're into the Blackberry-type experience, and don't mind being robbed of much of what makes Windows Mobile 6.5 interesting, there are a handful of devices--alas, not from all wireless carriers--that meet this need. (One example is the aforementioned iPAQ Glisten.)

I can't honestly recommend such a thing, and I certainly have no interest in such devices myself. I really feel that the new touchscreen Windows Mobile 6.5 user interface, particularly the new Zune-like home screen, is excellent. Yes, it's sitting on top of ancient underpinnings, with UIs that are old fashioned and not touch friendly. (For this reason, most Windows Mobile phones still ship with a stylus. Geesh.)

Windows Mobile 6.5: How does it compare?

To evaluate Windows Mobile 6.5 as it now stands, then, let's examine those qualities and capabilities that I previously identified as being central to any modern smart phone. For the most part, Windows Mobile meets the challenge, but it does surprise in a few areas too, both good and bad. Here's where we're at, circa early 2010.

Phone

While earlier versions of the Pocket PC system that preceded Windows Mobile treated phone functionality as an add-on of sorts, today's Windows Mobile 6.5 devices offers a more integrated experience, with Phone and Voicemail options right on the Home screen, quick access to Contacts from a soft menu on the Home screen, and a decent, touch-friendly Phone application. This latter app, however, doesn't stack up very well against the iPhone's Phone app, which provides a nicer, nearly full-screen keypad and simple access to favorite contacts, recent calls, the full contacts list, and voicemail.

To give you an idea of the differences, consider the iPhone's Phone Favorites screen. Instead of this handy interface, Windows Mobile provides Speed Dial, similar to the same feature on older phones, where you can assign frequently-called phone numbers to single digits. So to call the first name on the list, you could just dial "1" instead of navigating through a contacts list to find the right name. That's all well and good, but the iPhone Phone Favorites list is a lot handier, in my opinion, and doesn't force you to make weird name-to-number connections.

All in all, the Windows Mobile 6.5 phone experience is adequate.

Web browsing

Last year, Microsoft made a big deal out of its decision to port the Internet Explorer 6 for Windows rendering technology to Windows Mobile, and the resulting browser, which we'll just call IE 6M, is certainly a big step up from previous IE for Windows Mobile versions. That said, there are two glaring issues. First, IE 6 for Windows is obsolete, and Microsoft is actively trying to push its business customers away from this browser on the Windows desktop. And second, the WebKit-based browsers on iPhone and Android are arguably desktop-class and modern, and are much more sophisticated than Microsoft's offering.

It's not all bad, however. IE 6 for Windows Mobile does provide a first peek at the UI style that will grace future Windows Mobile 6.x versions, with big round and finger-friendly buttons, nice, readable soft menus, and a pretty nice way to switch between mobile and desktop-style web rendering. Instead of taking up valuable screen real estate with a toolbar of buttons and other doohickies (or keeping them at the logical top of web pages, as iPhone does), IE 6M hides most of the buttons when you're not using them, providing only a single menu-type button in the corner. Tap this, and the full complement of buttons appears--Back, Favorites, Virtual Keyboard, Zoom, and Menu, from left to right--as does the title bar and address bar. It's a nice design that really gets out of the way.

And unlike the iPhone, IE 6M actually supports Flash. Microsoft makes a big deal about this, as it should, though I have to say that the number of times I've come across an unusable Flash site on the iPhone over the past 2.5 years is pretty minimal: Maybe 5 or 10 times tops.

Where IE 6M sort of falls apart, of course, is that zoom functionality. Like Android's built-in browser, IE 6M doesn't support multi-touch pinch zoom effects, so you have to use an onscreen slider instead. This is harder to use and not as natural as the iPhone's zoom interface, which becomes second nature very quickly.

So, once again, Windows Mobile falls short, but we should give some credit to Microsoft for making up a lot of lost ground. This browser is at least usable; previously version of IE for Windows Mobile were terrible.

Email

Windows Mobile has always had decent support for email via its Outlook Mobile (previously Pocket Outlook) application. As you might expect, Windows Live Hotmail accounts are of course auto-detected. But it even auto-detects the settings for Gmail correctly (that is, as IMAP) without me having to fiddle with it, something that previously versions would have choked on. And Windows Mobile does a decent job of mixing different email (and contact) accounts together, not by providing access to multiple accounts inside the Outlook Mobile app per se, but rather via the neat "crossbar" UI used on the Home screen: Just scroll down to the email line and then move left and right across all the available accounts. That works nicely.

The way you manage email messages is still too ponderous, however, and this has been an Outlook Mobile problem for some time now. Let's say you want to move a read email out of the inbox. On the iPhone, as you view each message, you can very quickly archive a message (i.e. move it out of the inbox to some other folder) by tapping the onscreen Move button and then selecting the appropriate folder (All Mail, in the case of Gmail). It's fast and efficient. In Windows Mobile, it's neither fast nor efficient. You must tap the onscreen Menu button, then choose Move (or press M) from the pop-up soft menu, and then select the appropriate folder from the tree view that appears. The whole process kind of kills the efficiency of phone-based email management.

If you do use a Hotmail-type account, Windows Mobile is likely a better choice than the iPhone right now, though you can of course purpose a Hotmail-compatible email app for the iPhone if you want. Beyond that, the iPhone offers the superior experience.

Calendaring and PIM

Given Windows Mobile's PDA roots, you might assume that this system would offer a first class calendaring experience, and for the most part, you'd be right: If you're coming from Exchange or even a Google Calendar (via Google Mobile Sync) experience, it works wonderfully. Oddly and inexcusably, however, the Windows Mobile Calendar cannot sync with Microsoft's own Windows Live Calendar service, which makes this device curiously unsuitable for those who wish to fully utilize the software giant's solutions. I hope to see this omission fixed, but let's face it, it's been a year since Windows Live Calendar shipped. Shameful.

Media playback

Whereas the iPhone ships with what is arguably the world's best iPod in software form, Windows Mobile 6.5 comes with software that appears to be largely identical to the media player Microsoft first shipped in 2004 (see my review). Actually, it's not an exaggeration: The version of Windows Media Player included with Windows Mobile 6.5 is 10.3. Version 10 dates back to 2004, as noted above. Wow. The bad kind.

Messaging

Windows Mobile 6.5 sports old-school (i.e. Pocket PC-esque) looking Text functionality through the Messaging application. It supports both SMS (text) and MMS (multimedia) messaging, which is pretty much what you're looking for. (And it works with pictures, videos, and audio.) That it's integrated with voice mail is weird, but not disastrous.

App Store

Microsoft announced its Windows Marketplace for Mobile with much fanfare last year, and while the store can't compete with the iTunes Store from an apps volume standpoint, it does have an OK selection of apps, and one that is growing over time. As with iTunes, there are both free and paid apps, though it seems that some Windows Mobile apps are quite a bit more expensive than is the norm on the Apple side.

To gauge the effectiveness of the app selection, I took a look at the apps I actually use on my iPhone fairly regularly to see if there were Windows Mobile equivalents. The Windows Marketplace for Mobile did pretty well. I found Facebook, various Twitter apps, AP Mobile, a crossword puzzle app, and so on. Among the missing, however, were some apps I do really enjoy. A Kindle app. The New York Times. FlightTrack or any other kind of flight tracker. Any of the Rick Steves travel apps.

Obviously, there are mobile web equivalents for many of those. And as I noted, the Marketplace will grow over time. It doesn't have to equal the volume of apps on the iTunes Store (and it won't, of course), but it should at least be able to compete with the Android Marketplace. It'll get there.

I'll have more to say about Windows Marketplace for Mobile in the future.

Tethering

Unlike with the iPhone in the US, you can legally tether Windows Mobile phones through AT&T or any other carrier. This is basic functionality, and it's astonishing that AT&T hasn't moved more quickly to make it happen on the iPhone.

Choice

We've kind of beaten this one to death already, but suffice to say that choice is a double-edged sword for Windows Mobile. On the one hand, you do have a limited choice of devices, and from every possible wireless carrier, which is good. But the bifurcation of the product line into Standard and Professional editions is somewhat unfortunate, and confusing.

Upgrading

Because of Microsoft's relationship with the wireless carriers, Windows Mobile doesn't currently support a Windows Update-style system where the software giant can deliver true OS upgrades (like version 6.5.x or 6.6) directly to users. This is too bad, and something I'd like to see change. Apple regularly issues software upgrades, even major ones--Google does too, with Android. Windows Mobile should be no different.

Online backup and remote wipe

Microsoft offers a free and handy (if basic) My Phone service (see my review) that provides, among other things, extensive data sync between your phone and the cloud. So if you lose the phone or upgrade to a new one, getting everything back is a cinch. And I do mean everything: My Phone syncs contacts, calendar, tasks, text messages, favorites, photos, videos, music and documents. Pretty much everything but email. (And if you're doing email right, that won't be an issue anyway.)

It's hard not to compare My Phone to Apple's MobileMe service. And for the most part, the Microsoft service comes out ahead. It is free, after all. But there are some niceties to MobileMe that aren't present in My Phone. One of the more obvious, I suppose, is the Find My iPhone service, which helps you find a lost or stolen iPhone on a map, set a passcode remotely (so a thief can't get at your data), display a message on the home screen (so if it's found, a Good Samaritan can return it), or remotely wipe the thing, permanently removing all your data. Find My iPhone is really just an Apple friendly face on functionality that Microsoft has provided to corporate customers for some time. But Apple made it available to the general public, and added some unique functionality.

MyPhone offers a subset of this functionality to consumers via MyPhone. So you can find the device on a map, sort of: What it really shows is the location where it last synced with the MyPhone service. For a fee (via a premium version of the service), you get something closer to a "live" map of the device's location, and the ability to lock, erase, or ring the phone ... Maybe. It works only with certain devices and under certain conditions, according to Microsoft. It can't send a message to the lock screen, however.

To be fair, MobileMe is not "part" of the iPhone, and is something you must buy separately. MyPhone is a largely free service.

Advice and a look ahead

I've spent a torturous year trying to embrace Windows Mobile, first with version 6.1 and then with the more recent 6.5 release. But in its current form, I can't use or recommend Windows Mobile to anyone, even those people who are firmly in the Microsoft camp. The issue, ultimately, isn't so much the software itself, which is usually decent, but rather the lack of support, currently, for capacitive touch screens. This makes touch-based Windows Mobile 6.5 devices completely undesirable. And it's shame, because aside from some notable software problems--the lack of support for Windows Live Calendar, for example--the overall system is decent.

There are caveats, of course. There always are. If you're a business user, Windows Mobile has much to recommend it, and if you prefer the non-touch (i.e. Blackberry-style) form factor, there are various Windows Mobile 6.5 devices that will satisfy your needs. But these systems don't really offer a huge upgrade over previous generation Windows Mobile devices, as much of what is great about Windows Mobile 6.5 relates to its touch capabilities.

Even with new touch devices, of course, Windows Mobile 6.5 is a work in progress. And I suspect that as Microsoft improves this system over the course of early 2010, adding support first for capacitive screens and then for full touch access throughout the entire UI (and not just on the topmost screens), that Windows Mobile 6.5.x/6.6 will become something truly interesting.

Sadly, that's not the case right now. So I can't recommend Windows Mobile 6.5 to consumers, not yet. Not when there are better alternatives--iPhone and Android especially--and not when the current system is so unfinished. It will get there, and I'm looking forward to testing and using future Windows Mobile devices throughout the year. I think we'll have a different story to tell by the middle of the year.