Why MS-DOS Mobile Is Today's Best April Fools' Joke

The best jokes have a bit of a burn. They're funny because they're true, and they're unafraid to highlight something that makes you uncomfortable.

It's tough for companies to do that. Uber's play on Skymall doesn't highlight its problems with safety or regulatory issues. Google's Smartbox doesn't mock the company's collection of all of your personal data. They're funny, but safe.

Not so with MS-DOS Mobile. Am I being too charitable towards Microsoft to assume that it really thought this through? Because MS-DOS Mobile (with the Windows 3.1 interface add-on shown above, even) gloriously mocks Microsoft's No. 1 problem adapting to the new world of mobile computing: the tyranny of legacy.

DOS Past, DOS Now, DOS Forever
Okay, okay, okay, most people are not actually running DOS apps on their PCs nowadays. That was one transition that Microsoft actually pulled off. But the crushing dominance of Win32 legacy apps, primarily in business, has really restricted Microsoft's ability to move and grow over the past few years.

For mobile, Apple and Google were lucky enough to start from scratch just as a new generation of computing was budding. (Yes, Mac OS is out there, but even today it's a niche player.) I don't buy the "Microsoft is/was too late" argument, especially because Windows Phone 7 came out in 2010. Smartphone penetration in 2010 wasn't anywhere near what it is now. If Microsoft had played its cards right, it could have bitten a good chunk off of the growth of Android. But it wasn't just that Microsoft came to the modern mobile market late; it was that all of its other moves, such as offering Windows Phone for free to OEMs to compete with Android, also came late.

Microsoft's identity, and strength, have also been tied to Win32 for so long that it's become a horrible albatross. The company couldn't move properly into tablets because when users hear "Windows," they want to run Win32 apps, and when developers hear "Windows," they want to develop for that massive base of Win32 desktop customers. So Windows 8 became this hideous, chimerical balancing act of trying to drag users into a touch-focused world while maintaining all of that Win32 desktop compatibility.

"MS-DOS Mobile" is full of great little jokes. It's brilliantly done. You enter SMS text messages in an interface that looks like the DOS 5 text editor. When you browse the Web, it makes a "connecting modem" noise. And when you try to play a game, well, Cortana walks you through a painful, multi-step driver setup where you have to backtrack at one point and load the mouse driver into high memory. (The fake Windows 3.1 screen is less entertaining; it's just a bunch of shortcuts to existing apps.)

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Universal Apps Are Only a Start
I don't think Microsoft can go the Apple route of completely severing its desktop and mobile OSes. Too much of its value is based in the massive strength of Windows on the desktop (and of Xbox in the living room.) It's always needed to figure out how to bring all of these pieces together in a less awkward way than, say, MS-DOS Mobile.

With its Universal Apps approach in Windows 10, Microsoft is trying to do what it should have done with Windows 8, 2.5 years ago: leverage the Windows and Xbox developer communities to support each other, and to support Windows Phone. That's difficult, when you have to design apps that accept different screen sizes and input methods. But the global success of Android shows that it's not entirely impossible. Having excellent developer tools that smooth the path will be key, and we'll learn more about that at Microsoft's Build conference at the end of April.

For now, though, let's enjoy the self-aware self-mockery of Satya Nadella's Microsoft. "MS-DOS Mobile" shows that the company understands its problem. That's a good step towards solving it.