by Josh Fruhlinger

10 Ways Microsoft Tried and Failed to Rule Mobile

Mar 24, 2010
MobileOperating SystemsSmall and Medium Business

Take a tour through Microsoft's forgettable, regrettable mobile OS history.

Microsoft’s Windows Phone 7 is coming, and the buzz is good! A lot of tech observers are licking their chops for another entrant into the mobile market, with the added potential bonus of Microsoft and Apple duking it out anew, with the roles of industry giant and plucky upstart reversed.

Except … Windows Phone 7 isn’t the first much-heralded attempt by Microsoft to enter into the world of mobile OSes. The company that has dominated the PC operating system market for pretty much as long as that market has existed has never managed to find long-term success in anything smaller than a laptop, with its mobile offerings generally underwhelming customers — when they’ve ever made it out of the planning stage. And so, to add a cautionary note to the largely positive Windows Phone 7 coverage, we offer this tour through Microsoft’s mobile OS history — history that folks in Redmond have to hope won’t repeat.

Photo courtesy of viagallery

WinPad, aka Microsoft at Work for Handhelds


For everyone who loves or hates the iPad name, know that Microsoft did it first. In the early 1990s, the company was at work on products based on the alpha versions of the Windows CE embedded OS that underlies much of what you’ll see in this slideshow. One effort was known as WinPad; the Beta Archive has a treasure trove of screenshots of a PDA-like operating system, which are interesting to compare to Newton OS (under development at the same time) and Palm OS (which wouldn’t emerge until a year or so later).

WinPad’s trail is pretty cold, with only a few screenshots like these to prove that it ever existed. If this article from late 1994 has it right, the OS was to be rebranded with the much more typically corporate-clunky name Microsoft at Work for Handhelds; the article also notes that “Microsoft recently admitted it has yet to complete code on WinPad,” and, we assume, that code remains incomplete today.

Picture courtesy of the Beta Archive

Demo 2 Penpoint for ATT


When Microsoft began shipping real products for this form factor, they were based not on Windows CE, but instead on the contemporary desktop systems. Windows for Pen Computing 1.0 and 2.0 were sets of extensions for Windows 3.11 and Windows 95, respectively; you can get a brief glimpse of version 1.0 in the opening seconds of the video above, most of which focuses on AT&T’s equally doomed offering.

Windows for Pen Computing 1.0 actually came with a physical stylus, and offered a pop-up on-screen keyboard (sound familiar?) and the hardware was really quite elegant for the times. Unfortunately, the transition from 1.0 to 2.0 wasn’t easy, as this 1995 article in Pen Computing Magazine suggests. (Side note: There was a Pen Computing Magazine?) And pen computing itself never really took off, not least because of the absence of ubiquitous wireless, and the technology was allowed to die from lack of interest.

Palm-sized PCs and Handheld PCs


In 1996, Microsoft announced a new category, Handheld PCs, which were more or less equivalent to today’s netbooks; hot on its heels were the Palm-sized PCs (originally called just “Palm PCs” until the inevitable lawsuit from Palm Inc.). Both ran a version of the Windows CE OS.

In Palm, Microsoft encountered an OS rival that it couldn’t beat, at least not in the short term, Palm-sized PCs never took off; they were, however, the ancestors to the Pocket PC platform. The Handheld PC had a somewhat more devoted following, but eventually the company dropped the idea of a Windows CE-based OS for computers.

Picture courtesy of Wikipedia user Redhatter

Pocket PC/Windows Mobile


This entry is certainly the least floppy, least vapor-y of the bunch for this slideshow. There’s been a continuous series of Windows CE-based devices — PDAs and phones — released over the past decade, and they’ve sold respectively. In typical Microsoft fashion, they’ve come out under a dizzying and sometimes baffling array of brands, including “Pocket PC,” “Windows Phone,” and “Windows Mobile Classic.”

But if this branch of the Windows family tree can’t be called a failure, it can’t really be called a success, either. Certainly Windows Mobile never achieved the hegemonic status that its desktop cousin took for granted. And in recent years the platform has stagnated while the iPhone OS and other smartphone operating systems have shaken up the market. Windows Phone 7, though a direct descendent of this product line under the covers, will featured a completely revamped user experience in an attempt to catch up.

Picture courtesy of Old Shoe Woman

Windows XP Tablet Edition


In 2002, when Windows XP was still a basically brand new desktop OS, Microsoft unveiled with much fanfare a version for tablets, a sort of souped-up, modernized version of Windows for Pen Computing. Complete with handwriting analysis and voice recognition, this OS seemed to have everything it needed to power fully-featured computers that also happened to be tablets.

But things didn’t work out that way. The hardware for these machines often turned out to be underpowered and too warm for comfortable lap use. Despite the nods to other forms of input, Windows XP remains in essence a mouse-and-keyboard driven OS. And, in a recent New York Times op-ed, Dick Brass, who spearheaded the Tablet PC initiative, claimed that he was undermined in various ways by internal Microsoft politics; for instance, he claims the Office group’s VP refused to modify the all-important office suite so that it would work more naturally with pen-based input.

Windows XP for Tablet Edition saw a refresh in 2005, but the absence of Windows 7 Tablet Edition pretty much tells you what you need to know about Microsoft’s current dedication to the project.

Picture courtesy Ruben Diaz Alonso

Portable Media Center


By 2003, Microsoft had another mobile rival to contend with: the increasingly popular iPod. As is typical for Apple, the iPod was a combined hardware-software platform; and, as is typical for Microsoft, Redmond’s initial reposte was an operating system that hard drive-based music player manufacturers could license. Initially known internally as Media2Go, it later got the perfectly awful moniker Windows Mobile software for Portable Media Centers, which got truncated to the somewhat more sensible Portable Media Center.

The idea, at least in terms of branding, was to tie it to Microsoft’s proposed living room PC, which also had “Media Center” jimmied into its name (between “Windows XP” and “Edition”). The mobile version was demoed at CES in 2003 and available on gadgets from Creative a year later. Other manufacturers, including Philips, Samsung, and Toshiba, would follow suit.

Of course, all of these gadgets ended up as also-rans when compared to the iPod juggernaut, and just two years later Microsoft released its own music player, the Zune, which ran a not dissimilar OS. Microsoft stopped licensing Portable Media Center in 2007.

Picture courtesy dan taylor

Ultra-mobile PCs


In 2006, the Web trembled with anticipation, stoked by viral marketing, of a new product from Microsoft, dubbed “Project Origami.” ARumors were that it was a gaming device that would compete with the PlayStation Portable, in fact it was an attempt to build PDA-sized gadgets that could run full-on versions of Windows. At CES 2007, Bill Gates in his keynote presented the Oqo model 02, which was certified by the Guinness Book of Records as the world’s smallest fully functional computer. But consumer enthusiasm didn’t follow the initial splash. UMPCs tended to be underpowered and overpriced, and their keyboard arrangements bordered on the bizarre. Oqo, the company most closely identified with the trend, went out of business in 2009. But just as one small part of the dinosaur family — the birds — flourished and lived on, so too is the legacy of the UMPC still with us. One of the models launched during the early stages of the UMPC experiment was a more conventional looking if tiny notebook from Asus. Called the EEE PC, it’s widely regarded today as the ultimate progenitor of the wildly popular netbook.

Picture courtesy

Future vapor: Project Courier and Project Pink


Last fall, an unexpected furor arose as Gizmodo ran pictures and video of what it called Microsoft’s secret tablet. Dubbed “Courier,” it was a radical take on the tablet, a book-like computer with two screens attached with a hinge and operated by, yes, a stylus. But Courier failed to appear at CES, and despite Gizmodo’s reporting as if it were a done deal, Microsoft has breathed not a word about it. Current rumors say it will emerge sometime in mid-2010. Slightly more confirmed, but significantly fuzzy, is the Microsoft Pink. It’s been rumored for more than a year to be a joint Microsoft-Verizon answer to the iPhone. To be built on a Windows CE variant, and be aimed at users who are focused on social networking and instant messaging. The project is largely staffed with employees who came into Microsoft with the acquisition of Danger, maker of the once-trendy Hiptop. The weird overlap between Pink and Windows Phone 7 may have a lot to do with Microsoft’s culture of autonomous and sometimes competing business units.

Picture courtesy Gizmodo