It's been a year since Microsoft said it had a serious problem in making Windows Mobile cool enough to attract application developers and consumers. And since then, Redmond has done little to rectify the problem.

Last summer, Microsoft crowed it had thrashed RIM and Apple in the mobile market, but in 2008, Windows Mobile lost market share - the benchmark Microsoft now lives and dies by - to those very companies.

With Windows Mobile Marketplace due this fall, signs are emerging that Microsoft is targeting actual iPhone coders as converts to Windows Mobile for growth. Windows Mobile 6.5 is the vehicle Microsoft wants the iPhone developers to jump on.

Until now, Microsoft has simply been appealing to those disgruntled by the arbitrary and draconian rules governing Apple's year-old App Store. The company is also played the market share card: With 30 million mobile devices running Windows Mobile 6.0 and 6.1, there's potential to make money from an existing customer base.

But now Microsoft has turned to offering technical advice on how to convert iPhone applications to the planned Windows Mobile 6.5. Microsoft's released the story of Gripwire.com, which ported Amplitude to an early release of Windows Mobile 6.5 on an HTC Touch Pro phone.

Square peg, meet round hole

Major hurdles involved in the port underscored the fundamental differences that exist between coding for the iPhone and Windows Mobile - even version 6.5, which will close the gap a little with touch-based input. Constanze Roman, a Windows Mobile community program manager, said Visual Studio and MSDN can help developers close the programming gaps.

Among challenges Gripwire.com faced: the fact that processes run in the background on Windows but not in the background on the iPhone, the ability to adjust the screen orientation and accommodate phones with keyboards, and the fact Microsoft's .NET Compact Framework does not come with UI functions used by Amplitude.

Windows Mobile has been popular on mobile phones for business, thanks to its level of application support and integration with software such as Exchange and Outook.

But the growth for Microsoft is in smart phones that target consumers - and Microsoft knows this. As he was crowing about beating Apple at Microsoft's Financial Analyst Meeting (FAM) last year, the president of Microsoft's entertainment and devices Robbie Bach said that to reach about 400 or 500 million smart phones, Microsoft would "have to expand from just a work device to being a device for individuals when they're in their personal life as well as in their work life."

A year later, nothing has changed as Bach offered the same critique of Windows Mobile. In fact, things are worse for Microsoft. Windows Mobile lost market share to Apple - and RIM - in the smart phone market during 2008 according to Gartner.

"If I have a critique of our phones today, it's that our experiences are very good in the business case," Bach told this year's FAM, held last week.

"If you're in the consumer space, and you have consumer scenarios, you want to do more browsing, you want to do more media, you want to do more video, you want to do those types of things, our experiences aren't as rich as they need to be."

Reversal fortune?

Between FAM 2008 and FAM 2009, Microsoft announced Windows Mobile 6.5, which Bach promised would reverse Microsoft's fortunes with touch, services, and browsing.

"You will have a very rich browsing experience on 6.5 devices that will give you access to more Web sites than you will be able to get to on an iPhone, that will work actively and work well. It really is a much better experience," he promised.

It was classic Bach and Microsoft: no details on the roadmap or why anyone should want to drop Apple for Windows besides more talk of a "rich experience".

Bach also delivered more of the same generalities. He said Microsoft is building relationships, getting "the right integration" with hardware partners, and fulfilling "the need to work very closely with Samsung, Sony Ericsson and others to build a broad selection of phones."

There was nothing about what's coming after Windows Mobile 6.5, which Microsoft has said is just a step towards its fully touch-enabled Windows Mobile 7.0.

Culture war

Microsoft's been in mobile market for the best part of a decade, but Windows on mobile has never received the same focus and devotion as Windows on PCs and servers. Brands and architectures have shifted over the years, from Windows CE to Windows Mobile and now to the .NET Compact Framework. With the iPhone, it seems Microsoft has been guilty of underestimating the potential for Apple's success, possibly believing the world would one-day wake up after a brief fling and come back to Windows. That mistake goes right to the top of Microsoft.

We'll have to wait to see whether Roman's blog for iPhone developers is an isolated shout or whether this firms up into a coordinated campaign to woo iPhone developers - akin to the kinds of online campaigns Microsoft's tried on Internet Explorer 8 and Windows 7.

But the blog shows three things: that Microsoft knows it must act, that it realizes it needs iPhone coders, and that the gap between building for an iPhone and Windows Mobile is as big as it ever was for choosing between an Apple or a Microsoft stack - both in a technology and in a cultural sense. ®