My first experience with Microsoft's mobile devices OS came right at the beginning, in 1996, when the company sent me an NDA for a product, codenamed "Pegasus," that became Windows CE (for "consumer electronics," though Microsoft denies this now). Windows CE turned into Palm PC, then Palm-Sized PC, then Pocket PC, and finally Windows Mobile. (Windows CE continued on as the low-level OS on which these device OSes were based and was and is still used in embedded and other devices itself.)

The first Windows Mobile devices were of course PDAs, or personal digital assistants, a category of device that always fascinated me. But beginning a trend that would continue into Windows Mobile's use in smart phones, the competition was always more interesting than anything Microsoft could come up with. For years, I owned virtually every Palm device made, including those from Handspring and Sony, and it wasn't until the Motorola Q in 2006 that I returned to the Microsoft mobile camp.

It wasn't a happy relationship. Windows Mobile was old-fashioned, and when the iPhone came out less than a year later, I jumped shipped immediately, again seeking out a superior competing product. Microsoft tried to win me back over subsequent releases of Windows Mobile 6, 6.1, and 6.5, but by then the platform was doomed. Only Microsoft didn't seem to know it.

Windows Mobile was the source of one of my most awful Microsoft briefings, as well. That meeting is mentioned in the articles below, though I was polite enough to leave out the awful bit, which is essentially that, when asked when the company would ever get around to actually responding to the iPhone, I was told that the success of the iPhone "validated" what Microsoft knew all along: That when confronted with a truly innovative device, consumers would jump on the smart phone bandwagon en masse. A moment of uncomfortable silence occurred until I finally blurted out, "Do you even listen to the words that come out of your mouth?" This, of course, triggered even more silence.

Of course, Microsoft finally got its act together with Windows Phone. But that's a story for another day. Documented here are my largely unhappy experiences with Windows Mobile throughout the 2000s, as I wondered again and again when Microsoft would finally wake up.

As before, the newest articles can be found at the top.

Office 2010 Review, Part 4: Office Mobile 2010 - May 13, 2010

Microsoft's just-released Office Mobile 2010 suite of applications for Windows Mobile 6.5 is free and positioned as a mobile companion to the full, PC-based Office suites and applications.

Office 2010 Screenshots: Office Mobile 2010 - May 13, 2010

Screenshots of the final, shipping version of Office Mobile 2010.

Quick Take: Bing and Windows Live for Windows Phone - January 26, 2010

Now that I've got some modern Windows Mobile devices for testing purposes, I can turn my attention to some of the products and services that Microsoft has provided to accompany these devices. Key among them are two applications: The new Bing for Windows Mobile and a new version of Windows Live for Windows Mobile.

Windows Mobile 6.5 Review, Part 3: Hands-On with Windows Mobile 6.5 - January 23, 2010

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.

Microsoft's Plan to Save Windows Mobile - January 11, 2010

Windows Mobile 6.5 as shipped in late 2009 is not complete, and the software giant has continued working on updates to that system, updates that are now being delivered over time.

Windows Mobile 6.5 Review, Part 2: Defining the Smart Phone - December 14, 2009

In today's smart phone market, there is the iPhone and then there is everything else. Windows Mobile 6.5 is, however, roughly on par with Google Android 2, the system used by the Verizon Droid and numerous other smart phones. In fact, the similarities between Windows Mobile 6.5 and Android 2 are striking. Both offer similar user interfaces, though Android's is less elegant looking (if more consistent).

Windows Mobile 6.5 Review, Part 1: The Sky Is Falling, The Sky is Falling - November 6, 2009

Windows Mobile 6.5 is not as terrible as the gadget blogger goobers and Apple-friendly tech reviewers would have you believe. In fact, it's actually pretty good. But it also suffers from the same lack of ecosystem support that hampers Microsoft's Zune HD media player, when compared to the Apple offering. And that means that Windows Mobile 6.5, by and large, still can't compete toe-to-toe with the iPhone.

Microsoft My Phone - October 18, 2009
Microsoft My Phone, Part 2

My Phone is clearly a response to Apple's MobileMe service, a free service that synchronizes contacts, calendar appointments, tasks, photos, videos, text messages, songs, web browser favorites and documents between your Windows Mobile-based smart phone and your My Phone account on the web.

Quick Take: Palm Treo Pro - June 10, 2009

Palm's Treo Pro proves two things to me. First, Palm provides a quality product with an excellent synthesis between the hardware and software. And second, Windows Mobile phones don't have to stink. Far from it, in fact: The Treo Pro is an excellent smart phone.

Windows Phones 2009: Microsoft (Finally) Strikes Back Against the iPhone - February 21, 2009

This year, Microsoft will ship an interim Windows Mobile version, Windows Mobile 6.5, which finally seems to address the needs of a consumer market excited by the iPhone. 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.

Windows Mobile 6.1 - December 16, 2008

To understand the state of Windows Mobile, I've been using a Windows Mobile 6.1 smart phone for the past few months and, last week, I met with the Windows Mobile team again in Redmond. Windows Mobile 6.1 includes some interesting improvements over previous versions, but also some curiously ancient bits as well.

Windows Mobile: What Went Wrong? - October 15, 2008

Windows Mobile is doomed. Now, don't get me wrong here. I do believe that Microsoft could turn things around. But if the company continues on its current strategy for this increasingly irrelevant mobile platform, Windows Mobile will simply cease to matter and will, for all effects and purposes, cease to exist as well.

OTA: Over-the-Air Puts Mobile Email Over-the-Top - September 2, 2008

Today it's possible to access email wireless, or over-the-air (OTA), from a variety of mobile devices running on a number of mobile platforms. OTA changes everything: Instead of tethering a device to your PC, the device itself becomes a first class citizen in your computing experience.

Managing Your Life in the Clouds: Putting It All Together - August 17, 2008

From what I can see, Microsoft's offerings are the most comprehensive and cohesive. No, Windows Mobile hasn't generated the same level of excitement as has the iPhone (heck, even the Blackberry has somehow managed to wrestle mindshare from Microsoft's mobile platform). But Microsoft offers a set of solutions that work across all of the necessary platforms: The PC, the web, and mobile. If you're looking for a fairly seamlessly plug and play type experience, it's not a bad way to go.

Managing Your Life in the Clouds: The Microsoft Experience - August 13, 2008

At the time of this writing, Microsoft offers a comprehensive but incomplete cloud computing experience that provides web-, desktop-, and mobile-based access to most of its offerings. In this sense, Microsoft's PC history has paid off, with the company seizing on mobile and Internet opportunities as they arose and embracing and extending their core experiences.

Celio REDFLY Review - June 5, 2008

I've been able to spend some time with the Celio REDFLY over the past several weeks and would like to discuss the experience further. If you're not familiar, the Celio REDFLY is promoted as mobile companion for Windows Mobile smart phones, and it works with several recent models, including the AT&T-based HTC Tilt that came with the pre-production REDFLY I've been evaluating.

Celio REDFLY Photo Gallery - June 5, 2008

Here are some photos of the Celio REDFLY min-laptop add-on for Windows Mobile.

Celio REDFLY Screenshot Gallery - May 9, 2008

Here are some screenshots of the Celio REDFLY in action.

Celio REDFLY: A Companion for Windows Mobile Users - March 19, 2008

Made by Celio, REDFLY is like a mini-laptop computer, weighing just two pounds, which connects via Bluetooth or USB to your Windows Mobile smart phone, providing more onscreen real estate and a true keyboard.

Windows Mobile 6 Preview - February 15, 2007

About two weeks ago, sitting under the harsh glare of a spotlight that was pointed at an animated fish, nearby a talking moose which, curiously, appeared to have actor John Goodman's voice, I learned all about Windows Mobile 6, the next version of Microsoft's OS for smart phones and PDAs. Yes, we were at "Bugaboo Creek," which is a family-friendly Canadian steak house chain. So what does this have to do with Windows Mobile 6? Not much. And let's be honest: It wasn't even the weirdest place I'd ever had a Microsoft briefing.

Windows Mobile Marches Forward - December 26, 2006

I recently began using the Motorola Q, a Windows Mobile 5.0-based smart phone that's sold via Verizon in the US. The Moto Q is pretty close to that perfect all-in-one portable device I've wondered about for years, and now that I've used it for a few weeks, I'm surprised to report that it's had precious few problems. Here are a few notes from my experiences with the Q, which will be especially helpful if you've not looked into Windows Mobile recently.

Reexamining Windows Mobile - December 12, 2006

Windows Mobile 5.0 isn't perfect, and certainly the Motorola Q isn't either. But the dream of an all-in-one device that does it all is a heck of a lot closer now than it's ever been, and maybe it's time to jump in with both feet.

Microsoft Mobility Tour - March 14, 2003

Here are my slides from the 2003 Microsoft Security Road Show - San Francisco, Los Angeles, Dallas, Miami, Atlanta, New York, and Chicago - January to March, 2003.