Over two years, ago, in January 2007, Apple announced its first smart phone entry, the innovative and stylish iPhone (see my review). To say that the original iPhone--despite obvious and deep flaws, especially for Windows users--set the mobile industry on its head is clearly an understatement. But that first iPhone was just the beginning. Apple updated its iPhone software again and again, slowly at first, but more quickly and more promisingly over time, and released a second generation device, the iPhone 3G, in mid-2008 (see my review). It also released a phone-less (and, more important, contract-less) iPhone called the iPod touch (see my review), which is now also in its second generation (see my review). Between these hardware and software updates, the iPhone/iPod touch of today is a far more capable and complete solution than was that original device. Apple, clearly, has done it again.

But what about the Microsoft side? Surely Microsoft has done what it can to keep up with the iPhone, which brought smart phones to the masses.

Not exactly. Instead, Microsoft focused on its bread and butter business customers, offering such technologies as over-the-air (OTA) Exchange support and Outlook interoperability. But its software, both on the devices and the PC desktop, has been lackluster and utilitarian. Right after Apple announced the first iPhone, Microsoft began talking up Windows Mobile 6 (see my preview), which didn't start petering out with new devices until late 2007. By early 2008, with Apple talking up the iPhone 3G, Microsoft was pushing Windows Mobile 6.1, while new devices based on this version would again trudge into market later, at the whim of device makers and wireless carriers.

Where was the excitement? Depending on who you talk to it, the excitement was locked behind closed doors at Microsoft: Its Windows Mobile 7 system would be rewritten from the ground up and would blow the iPhone out of the water. Or it would be the same old thing with a slightly prettier new face. There were stories of internal rivalries at the company, each convinced that it has the answer Microsoft needed to address the iPhone and Apple's opening of a much, much bigger market for smart phones.

And then there's what's really happening. Yes, Microsoft will one day ship a Windows Mobile 7. But that release won't happen until the end of 2010 at the earliest, meaning we're looking at first half of 2011 for actual devices. That's two years from now. This year, Microsoft will instead ship an interim Windows Mobile version, Windows Mobile 6.5, which finally seems to address--at least in some ways--the needs of a consumer market excited by Apple quality and functionality. This OS will be bolstered by an online application store, called Windows Marketplace for Mobile, which is clearly inspired by the iPhone's popular App Store. And it will be backed by a free online sync service, My Phone, that is equally clearly a copy of Apple's Mobile Me service (see my review).

Yep, that's where we're at. Microsoft is copying Apple again.

Of course, this strategy has often paid off in the past. In fact, the entire PC market can be seen as the cancerous aftereffects of Microsoft's earliest example of Apple envy. The question here is whether it can work this time as well.

With that in mind, I will examine Windows Mobile 6.5, Windows Marketplace for Mobile, and My Phone extensively in the months ahead. This article serves only as an introduction, and is so often the case with previews, it comes before I've had a chance to actually spend time with any of these products and services. Expect my views to change over time.

Windows Mobile 6.5

Looking at today's Windows Mobile versions, a few obvious problems emerge. Here, I'd like to list some of those issues and discuss how Windows Mobile 6.5 does (or does not) appear to address them.

User interface

The Windows Mobile user interface is ancient and utilitarian, and dates back to the first Windows CE user interface from 1996. Microsoft has tried to address this with friendlier home screens in Windows Mobile 6 and 6.1, but let's be serious: These home screens only temporarily masked the ugliness of Windows Mobile, which would come the forefront the moment you dug deeper into the system. The iPhone instantly and inexorably made all other smart phone designs seem old fashioned by comparison, but that's even more true with Windows Mobile. It doesn't just need a makeover, it needs a complete rewrite.

What Windows Mobile 6.5 does. Windows Mobile 6.5 features yet another new home screen design but does not significantly alter the majority of sub-screens users will encounter in day-to-day use. That new home screen, as before, acts as a dashboard to the information that is most important to users (new email, calls, and so on). This time around, we get a nonsensical honeycomb design, apparently because Apple cornered the market on a clean grid of beautiful icons. Fair enough. But dive deeper and the ugliness returns.


Windows Mobile 6.5 offers a thin UI layer over the same old mobile OS.

Windows Mobile 6.5 also apes the iPhone's innate touch screen functionality in the same way that Windows 7 does on the PC. That is, instead of writing a touch screen OS from the ground up, Microsoft has simply adapted its existing OS by making UI elements like buttons bigger (and thus more touch-friendly).

Preliminary verdict. Windows Mobile 6.5 does not address the very real problems with Windows Mobile and instead provides yet another skin-deep UI change. More confusing: Microsoft already has a perfectly workable and attractive UI on its Zune devices. Why not just use that for Windows Mobile?

Web browsing

While Apple's Safari isn't exactly the compatibility king on the PC desktop, one of the iPhone's biggest successes has been getting people to access the Web with a pocket-sized mobile device. The reason Apple was able to do this is that Microsoft's entry, Internet Explorer, has been a sad joke on Windows Mobile since, well, forever. That Microsoft had a mobile browser years ago and did absolutely nothing worthwhile with it should make any potential Windows Mobile user reconsider things.

What Windows Mobile 6.5 does. Last year, Microsoft announced that it was working on a new Windows Mobile version of Internet Explorer. That browser will be included with Windows Mobile 6.5. That's good news. Its rendering engine, however, is based on the version of IE 6 that first shipped for PCs back in 2001, almost a decade ago. Sadly, that's good news too: Compared to what Windows Mobile users put up with today, IE 6 is actually pretty decent. It will even include support for Adobe Flash, a feature the iPhone version of Safari currently lacks.


Internet Explorer for Windows Mobile 6.5 seeks to provide a much more seamless browsing experience than its predecessors.

Preliminary verdict. This new version of Internet Explorer Mobile can't happen quickly enough, but then neither can the next version. Anything is an improvement over the old versions. Will it be enough to beat Safari on the iPhone? Honestly, I doubt it.

Choice

If ever there was a mixed blessing, it's Microsoft's decision to rely on a vast ecosystem of device maker and wireless carrier partners to bring Windows Mobile to end users. (This has actually dogged Apple somewhat too: Today, AT&T is still the iPhone's weakest link.) On the plus side, the variety of the offerings seems to provide a healthy amount of choice, and consumers can indeed choose between a number of device types, each with unique capabilities, pros, and cons. On the minus side, this choice also leads to confusion, because each of these devices has unique capabilities, pros, and cons. Different wireless networks perform differently in different places, and some work overseas, while others don't.

Worst of all, Microsoft's partners are slow. Every time Microsoft ships a new Windows Mobile version, it takes several months before the first devices based on that system appear. And even then, those devices aren't available on all carriers. It's much longer than a year before a decent selection of devices based on that new system are broadly available.

What Windows Mobile 6.5 does. Absolutely nothing. Once again, Microsoft is relying on its slow-moving partners to deliver Windows Mobile 6.5 phones. So even though the software giant will complete the OS this quarter, we won't see more than a couple of Windows Mobile 6.5 devices by the end of 2009. I hope they're available on the carrier I use.


Two of the first Windows Mobile 6.5 phones: The HTC Touch Diamond2 (left) and Touch Pro2 (right).

Preliminary verdict. There have been persistent rumors--which Microsoft just as persistently denies--that the software giant will build its own phone. And more than one Microsoftie has uttered the phrase "Zune Mobile" in my presence. I hope and recommend that Microsoft goes its own way in the mobile space. Its partners have never done anything other than hold back Windows Mobile.

Upgrades

Another issue that arises out of Microsoft not controlling its ecosystem is that the company's wireless carrier and device maker partners very rarely offer consumers the option to upgrade to newer Windows Mobile versions. (Yes, it does occasionally happen. But in the PC world, virtually anyone who buys a PC the year before a new Windows version comes out can purchase and install a Windows upgrade themselves.)

The reason for this is simple greed: These companies would rather sell you a new phone--and extend your contract out another two years--because they think of the phone as a toaster. But smart phones are computers and you should be able to upgrade the capabilities of that device just as you can with a PC. In fact, this is one of the huge advantages of the iPhone.

What Windows Mobile 6.5 does. Nothing specific. But it's notable that two of the three Windows Mobile 6.5 smart phones that Microsoft announced this past week (the HTC Touch Diamond2 and Touch Pro2) will ship first with Windows Mobile 6.1 and then become upgradeable to 6.5 when that OS version ships.

Preliminary verdict. This is slightly encouraging, but it doesn't indicate a trend. I fully expect most Windows Mobile 6.5 devices to be Windows Mobile 6.5 specific. Microsoft should sell Windows Mobile upgrades directly to end users.

Windows Marketplace for Mobile

When I asked Microsoft last year how it was planning to respond to Apple's hugely popular App Store for the iPhone, I was told that Windows Mobile was supported by a rich ecosystem of over 18,000 third party applications and that these applications were broadly available from third party partners like Handango.

Now, anyone who's actually used Handango will tell you that the experience isn't exactly seamless, but then part of the problem is the wide range of Windows Mobile versions, devices, and capabilities out there as well: Applications just don't run consistently on different Windows Mobile devices. (This speaks to two of the issues I raised above. First, that the "choice" offered by the Windows Mobile ecosystem is in fact a double-edged sword. And second, that not allowing Windows Mobile users to upgrade is a problem; now, application writers have to worry about the differences between all those OS versions as well as hardware differences.)

Microsoft is stealing a page from the Apple play book and creating their own online storefront for Windows Mobile. Imaginatively named Windows Marketplace for Mobile (and Microsoft gets bonus points since this service is being named in the wake of the company's decision to shut down the PC version of Windows Marketplace), this online service will allow Windows Mobile users to browse, search for, and purchase applications for their devices.

Sadly, the service will require Windows Mobile 6.5 (which, remember, most existing Windows Mobile users cannot upgrade to) and will apparently only run on the phone. (And not on the PC or Web as well, though I will verify that.) It will require a Windows Live ID, which is certainly acceptable.

My Phone

The most intriguing of these offerings, perhaps, is My Phone, which provides Windows Mobile users with a way to synchronize and backup their important smart phone data to the Web. This looks good for two reasons: First, it will work with at least some legacy (i.e. pre-6.5) Windows Mobile devices. Second, it will be absolutely free, unlike Apple's disastrous if well-intentioned Mobile Me service. (For which Apple charges a whopping $99 each year.)

The Mobile Me connection here is important. Sure, Microsoft is copying Apple here, again. But for all of its promise, Mobile Me continues to be an epic disaster on the PC because Apple, quite simply, has never gotten PC sync right. It botched Outlook and other PC data point sync on the original iPhone (and since), and it botched it in Mobile Me. It just doesn't work. That you pay for it makes Mobile Me an insult, especially to Windows users.

That said, the idea is a good one: Rather than strand your data in a single location--wherever that might be--you should be able to sync it to all the places that are important to you, including your phone. If you make a change to a contact or a calendar item from any location--PC, Web, phone--it should automatically sync to all the others. And if you get a new phone, syncing all your old data to that new device should be seamless and simple.


My Phone contacts sync.

My Phone seems to address this need and appears to sync and backup contacts, calendar, tasks, text messages, photos, videos, music, documents. What's not yet clear is if the expected links to Windows Live services like Windows Live Photos, SkyDrive, and People are there (yet?). I'm sure they will be. And since My Phone is now available in a semi-public beta, I'll be able to get up and running with this service before I ever lay my hands on Windows Mobile 6.5 or Windows Marketplace for Mobile. (In fact, if I hadn't been on vacation this week, I already would have done this.)


My Phone photos sync.

My Phone has the chance to be a real deal maker, though of course the other Windows Mobile pieces will need to mature as well.

Final thoughts

Given the ongoing success and momentum of the iPhone and the growing stable of consumer-oriented smart phone competitors, Microsoft really needed to hit a home run with its 2009 Windows Phones announcements. If you'll excuse me for beating the baseball metaphor to death, what it achieved was advancing the runners without scoring a run. Put simply, Windows Mobile 6.5 isn't enough to stem the iPhone tide, and phones based on this system will not appear in volume until after Apple has shipped a third generation iPhone. The related services, Windows Marketplace for Mobile and My Phone, are useful but obvious. I'd love to get excited about Microsoft's mobile moves, but I think the company is being too conservative and is moving too slow in a market that requires dynamism and good design. These products all lack both and, I think, will suffer for it. And why is this taking so long? Late 2009 is too late to respond to a product first introduced in mid-2007.