Memo to Microsoft: It’s Time for Windows 365

With the launch of Office 365, Microsoft has taken another big step towards making sure one of its two superpower products remains relevant in the cloud world. But it begs the question: what is the software giant going to do with its other franchise player in the cloud?

In many ways, the introduction of Office 365 leaves the venerable Windows operating system alone in Microsoft’s stable of heavy hitters stuck in the old desktop and client-server world. Thus far, Redmond hasn’t been talking too much about what the cloud means to Windows. But that doesn’t mean there isn’t an opportunity to update how businesses procure and manage Windows in a world where companies are more receptive to paying ongoing subscription fees as opposed to upfront capital costs.

At its giant Worldwide Partner Conference last July in Washington, D.C., Microsoft proudly proclaimed that it was “all in” when it came to the cloud — and urged, cajoled, begged and threatened its thousands of solution providers partners around the world to do the same. And yet there seems to be very little of an online strategy in place for the bigger of the company’s two crown jewels.

To be truly “all in” when it comes to the cloud, and to convince its partners and customers that this belief is more than just a marketing slogan, Microsoft doesn’t need commercials that do little but muddy what it exactly it is the cloud means to businesses.

It needs to find a way to update how Windows is purchased and managed — whether that’s by offering an Operating System-as-a-Service model (let’s call it Windows 365, just for fun) or by including upgrade rights to the freshest versions of the operating system with subscriptions to a service like Office 365.

The notion of tying Windows to an online platform is not exactly a new one — the company is already doing it with its Windows InTune management tool. In short, each seat of Windows InTune comes with “upgrade rights” to Windows 7 and presumably this will continue once Windows 8 sees the light of day, meaning that InTune customers have a clear path to having managed desktops running the latest version of Windows at no additional cost.

Microsoft’s motivation for this is clear: With InTune it’s responsible for a variety of metrics around uptime and performance, and by including Windows in the deal, it’s hopeful that it will have fewer versions of its own platform to test for compliance again and to iron out bugs with.

That motivation isn’t present with Office 365 or any other future Windows-as-a-Service offering. But there is another and much more pressing motivation for this — Microsoft needs to do so for Windows to continue to matter.

Microsoft is already tacitly, if perhaps grudgingly, acknowledging the reality of a cloud world where choice of OS matters less than ever in promoting that Office 365 can work natively with the company’s Office for Mac suite, or via a number of browsers, including Firefox, Safari and Chrome, on a wide variety of platforms.

Would Windows-as-a-Service cannibalize Windows sales? Not really. It would just shift how Windows is purchased. Just as Office 365 allows users to go from paying a big upfront fee for Exchange, SharePoint and Lync to paying for it on a subscription basis, so a subscription service for Windows — be it as part of Office 365 or part of something else altogether — would do for the desktop platform.

It doesn’t mean companies stop paying for the operating system. It just means they’re just renting their license at a monthly rate rather than purchasing it upfront. That introduces some challenges in terms of management, but none above and beyond those that already exist. But it offers tremendous potential benefits in terms of security, agility and flexibility.

But perhaps the biggest impact for Microsoft, and for its customers, would be the reduction in the need to support old, out of date versions of Windows for which security and other updates are hard to come by or not offered at all.

For small businesses, creating a — pardon the pun — canonical version of Windows would introduce short-term pains in that all applications and systems would have to be brought into compliance with the new version. But in the long run, it could be a benefit. Security holes can be patched from the cloud rather than the rather archaic tools and practices often used today, which are sometimes little better than sneakernet.

One of Microsoft’s biggest challengers and competitors, is, was and always has been “good enough” — companies that stick with old versions of Windows and Office not because new versions don’t offer some benefits, but because of the cost and complexity of updating. With Office 365, it’s taken an important first step to combat this all-too-familiar foe on the applications suite level. Can (and should) a similar step at the OS level be too far behind?