Throwback Thursday: Windows Mobile 6.5

Just two years after the original iPhone was released, Windows Mobile was on the ropes and Microsoft realized it needed to embrace changes like multi-touch while moving more quickly in this suddenly hot market. Its last-ditch effort was the ultimate example of “putting lipstick on a pig” in the form of a touch-friendly patina over a legacy stylus-based UI: Windows Mobile 6.5, the last-ever version of Windows Mobile.

I had met with the Windows Mobile team in Redmond. Everything they did and said was oblivious and I became even more convinced that my decision to switch to the iPhone in 2007 had been a good one. Everyone at the table was using a Palm Treo Pro handset, which ran Windows Mobile 6.1 Professional and could be purchased for several hundred dollars, a sum that was at that time unthinkable. There was talk about coming improvements in the next release, Windows Mobile 6.5.

Yeah, yeah, yeah. But how or when, I asked, would Microsoft respond to the iPhone threat?

I remember some things very clearly. I will never forget the answer I received to this question.

“The iPhone validates what we’ve thought for a long time,” I was told. “That consumers would embrace multi-touch capabilities on smart phones.”

Somewhere in the middle of that sentence I had stopped taking notes. Was probably rubbing my temples in some effort to not totally lose it.

What I was thinking was: “Are you telling me that you saw this coming but did nothing about it? Is that really your answer?” But what came out of my mouth was even less political. “Do you even hear the words that come out of your mouth?”

That October, Microsoft released Windows Mobile 6.5, its first real answer to the iPhone. Rather than start over from scratch—which the firm belatedly did in 2010 with Windows Phone 7 Series—it upgraded the existing Windows Mobile OS.

Windows Mobile 6.5 was simply Windows Mobile 6.1 with a few new UIs, each of which was actually pretty good.

There was a lock screen that let you swipe on individual items—like a text message or phone call—to open the corresponding app, a feature that Windows Phone lacks 6 years later.

And there was a new touch-friendly Today screen, a textual list that somewhat mimicked the Zune home screen.

Plus a Start screen with offset icons over wallpaper instead of Explorer windows. How modern!

Below that, of course, was the tired old Windows Mobile OS, which included tiny UI elements that could only be accurately tapped with a tiny stylus. It was kludge.

But here’s the real irony to Windows Mobile 6.5: At the time it was released, Microsoft was already moving on to Windows Phone. Indeed, Windows Mobile 6.5 devices were already being branded as “Windows Phones” to get the market place ready for the coming change. And a planned Windows Mobile 7.0—codenamed Photon and another waste of time and effort—was cancelled.

Looking back on my notes from another meeting with Microsoft, this time about Windows Mobile 6.5 right after the launch—I missed the Windows Mobile 6.5 launch because I had gone to The Netherlands to appear in the Windows 7 launch—I’m stuck by a few things.

Enterprise focus. Microsoft was focused on enterprise first with this release, a strategy it would completely overturn with Windows Phone, which was initially going after the same consumer market as iPhone. The “killer app,” I was told, was Exchange support.

Some consumer appeal. Microsoft was starting to understand that consumers mattered. With Windows Mobile 6.5, there is the first sense that Microsoft was trying to appeal to an audience beyond information workers.

Touch. The key investments in this release were all touch-related and thus trying to answer the iPhone: Multi-touch support, gestures (flick, pan, zoom, and scroll), and “finger navigation.” This seem quaint today, but for the slow-moving Microsoft of 2009, this was a big deal. “Touch is big now,” I was told, “but we don’t want to forget the stylus legacy.” Yikes. And get this: There were no capacitive touch screen-based devices offered. Touch was there, but it was hard to use.

My Phone. The one thing Microsoft did get right with Windows Mobile 6.5 was a new service called My Phone that was subsequently killed when Windows Phone launched and never really duplicated: it was a free service for Windows Mobile users that backed up your content—like pictures, text messages, non-Exchange contacts and calendar—and so on to the cloud. So if you lost your phone or whatever you could sign in with your Live ID (today: Microsoft account) and get it all back. My Phone was actually pretty great.

Windows Marketplace for Mobile. Recognizing that the year two App Store that really put iPhone over the top (well, that and massive price cuts), Microsoft created a mobile app store for Windows Mobile too. It supported trial apps, which Apple didn’t offer, and full refunds on app purchases in the first 24 hours (ditto).

Partner strategy. As today, one of the things that really dogged Microsoft was its insistence on sticking to the strategy that worked so well in the PC space: It relied on hardware partners and wireless carriers to get the phones to customers. Over 30 new phones were expected by the end of 2009, I was told.

Still offered two product versions. Amazingly, Microsoft still offered Standard and Professional versions of Windows Mobile 6.5. Devices with very small (320 x 240) screens typically (but not always) ran Standard, which lacked most of the important new UI stuff that made Windows Mobile 6.5 at least somewhat interesting. Professional devices included the touch screen capabilities, the new user interface, and so on.

I couldn’t recommend Windows Mobile 6.5 at the time and looking back on it now, I can see why: Microsoft made major strides with Windows Phone 7—a system that was so good I switched from iPhone and never looked back—but Windows Mobile 6.5 was a freaking disaster. “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,” I wrote at the time.

What a dud.