Windows Mobile leaves a legacy of failure but hope for the future

Microsoft was early to recognize the potential of smartphones -- so early in smartphones, in fact, that it had a presence in mobile handhelds before the smartphone was really a thing. Its Windows CE operating system powered many PDAs that preceded them.

But like all of Apple's legacy smartphone OS competitors, Microsoft was late to respond to the iPhone, preferring to take swipes itself rather than enable them on touchscreens. Things didn't look promising when Microsoft, so late to the game, could say only that Windows Mobile was "different" and not assert that it was better.

As (former) Windows Mobile head Joe Belfiore succinctly tweeted, Windows Mobile began an arduous odyssey in mobile that included paying developers to attract apps, phone manufacturers to produce phones, buying and then dismantling Nokia.

Along the way, there were many missteps including typical Microsoft product name bewilderment and, more seriously, atypical poor upgrade paths from Windows Mobile 7 to Windows Mobile 8 and then again from Windows Mobile 8 to Windows 10 for Phones.

During those transitions, Microsoft worked diligently to bridge the third-party development gap between Windows on the desktop and the phone. Paradoxically, the company is ending Windows 10 for Phones development not long after reaching the pinnacle of that effort.

Also paradoxically, the dismantling of Windows Mobile began within months of the Nokia phone business acquisition with the start of the Nadella era in early 2014, two months before the Nokia deal closed. There were many signs leading up to the end of Windows Mobile/Windows for Phones, including the extensive development of Microsoft apps and services for its rival platforms.

Apps like Office 365, Skype, and Cortana will now serve as the foundation for the company's smartphone presence. As the company notes, many of its customers (including its co-founder) use iOS or Android (of course, given their combined market share) and it's important to extend ties to Windows-centric services on those platforms.

Microsoft has a greater if still challenging opportunity with the more malleable Android, an opportunity it and others have sought to exploit with results that have included abject failures (Nokia's X series and Microsoft's investment in CyanogenMod), modest success (Amazon's Fire tablets), and widespread if contained success (Google-free Android smartphones sold throughout China).

The latest push to Microsoftize the Android experience comes via the Microsoft Edge app, as well as the Microsoft Launcher app, originally launched two years ago as the Arrow project from its Microsoft Garage effort that produced almost all of its apps for iOS and Android. One of the launcher's goals is to help bridge desktop-mobile experiences such as the cross-device Clipboard and OneDrive files-on-demand.

When Microsoft demonstrated these features at its Build event, the appeal of their functionality was undercut by the friction they encountered trying to integrate with foreign operating systems, particularly iOS.

Microsoft gives up a few potential advantages by burying mobile Windows. For example, while it offers Cortana on iOS and Android, Microsoft's digital assistant will be hard-pressed to compete with the native agents on those platforms. Furthermore, as Google had to do with Chrome, Microsoft will have to forego its own rendering engine on iOS for Safari's. Even on Android, Edge will struggle to compete with Chrome based on how its desktop cousin has fared.

On the other hand, staying out of the mobile OS playground will encourage cooperation from former rivals such as Apple, which has been promoting Office on iOS for some time even as the company's Surface group pokes the MacBook and iPad.

Windows Mobile and its shorter-lived successor were as much a victim of larger marketplace shifts versus a longstanding competitiveness deficit. These have included Microsoft refocusing on profitable corporate customers who don't require the kind of marketing outlay needed to succeed among the mass market. If anything, smartphone giants Apple and Google are doubling down in terms of surrounding their mobile platforms.

Microsoft's exit also comes at a time when the smartphone market is coming to terms with its middle age (in terms of technology lifecycles). As I wrote regarding Google's hardware efforts, the near-parity we are seeing in terms of premium smartphone features has dulled the ability to draw meaningful differentiation among them.

One consolation for the company is that its work on getting Windows 10 running on Qualcomm-based smartphones has likely paid off in Qualcomm Snapdragon-equipped PCs due to appear in the coming months. It would not be surprising to see Microsoft reboot the non-Pro Surface line with this processor (returning the Surface to its ARM roots). Microsoft lost the battle of the decade, but is cultivating technologies, particularly Cortana, that could drive a disruptive mobile return where agents labor to to touch our lives instead of us laboring to touch our phones.

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