Windows as a Service Isn’t Working

Microsoft has tried to treat Windows 10 like a cloud service, with ongoing, seamless software updates. But just over a year into this new era, it’s very clear that this plan just isn’t working.

It was such a beautiful dream.

Back in January 2015, Microsoft’s Terry Myerson described a future in which customers would be upgraded seamlessly to Windows 10, and where Windows 10 would be upgraded continuously, keeping it up-to-date for the betterment of all. Microsoft calls this scheme Windows as a Service.

The examples Microsoft provided at that time—200 million customers upgraded to Windows 8.1, 650 million to Windows 7 Service Pack 1—should have been seen as a warning, not a proof point. Those monolithic upgrades in no way indicated that Microsoft would be able to upgrade Windows continuously; in fact, each release took several months to complete, and each required a lengthy series of follow-up fixes.

“In the next couple of years, one could reasonably think of Windows as one of the largest Internet services on the planet,” Mr. Myerson said at the time. “And just like other Internet services, the question, ‘what version are you running?’ will cease to make sense … Windows as a service is great for consumers. It’s great for developers. And it’s great for the security of our enterprise customers.”

It would be cynical and unfair to call Windows as a Service a lie, and my goal here isn’t to badger, or complain, but to point out a problem. I know from speaking with Microsoft many times that the intent was and still is true, and pure. And that the software giant believes, collectively, that it, its users, its developer base, and IT teams from around the world would all be better off because of this new way of doing things. If only it worked.

But it doesn’t work. Instead, we’re all in a perpetual beta, where the speed of these updates and the explicit understanding that they will always be followed my more updates, means that quality control can lapse. If Microsoft screws up an update, no worries: They can and will just patch it again, because they can. And patch it and patch it and patch it. Which they have.

Forget for a moment the mess of the weekly and monthly updates we see. Let’s just look the major upgrades.

Since July 2015, Microsoft has released three major OS releases, even though only one of them, the original Windows 10, was marketed as such. But Windows 10 versions 1511 and 1607 were in fact major OS releases too. They are delivered, installed, and serviced as such, and they come with the same risks as any major OS upgrade. They might have been branded as Windows 11 and 12 had Microsoft not arbitrarily decided to stop the branding at Windows 10 and pretend that this was the final version of Windows.

The result: We’ve had to install, troubleshoot and maintain as many new versions of Windows in the past 15 months as did in the 6 years between Windows Vista in 2006 and Windows 8 in 2012. Think about that for a moment. (And then remember that Windows 8 was so bad it needed two major updates of its own, Windows 8.1 and Windows 8.1.1, to set things right.) And when you add in Windows 10 version 1703, you get four major Windows upgrades in just two years.

And that, essentially, is the problem with Windows as a Service: It has created more platform fragmentation, not less. That was not the goal of this initiative.

Let’s do some more math. As of March 2017 or so, Microsoft and its customers will have four versions of Windows 10, plus two other Windows versions, 7 and 8.1, to support. So much for simpler servicing: Had Microsoft simply not gone down the Windows as a Service path, it would have only three to support: Windows 7, 8.1, and 10. But instead, it will have 6. That’s double the number of supported platforms, double the attack surfaces to protect, and double the number of patches it needs to create for the same problems. Again, it’s more fragmentation, not less. A lot more.

(And it’s even worse when you consider the impact of the Windows Insider program, which ratchets up the complexity by providing other versions of Windows 10 that Microsoft must support and maintain, and monitor for feedback. It’s hard to even contemplate the matrix of software versions that Microsoft has wrought here.)

Even if the quality of Microsoft’s upgrades was rock solid, the sheer amount of complexity of all these versions would have made Windows as a Service untenable. But we all know that Microsoft’s update quality is not high. In fact, at a time in which Microsoft needs to convince its customers that this scheme will work, it has done the opposite and delivered an incredible number of unreliable updates. As a result, the past year or so has been a horror show for many of its customers.

The effect that this uncertainty has on this customer base is chilling. If you can’t trust the platform maker, alternatives start to look more compelling. I’m not aware of any issues with Chrome OS, for example, and that platform is also being rapidly upgraded. And while I have heard of occasional issues with macOS upgrades, or with Apple upgrades in general, that’s only because I am paying attention: Apple’s platforms do not suffer from the number of problems that Microsoft’s do.

There is one potential bright spot here: As is the case with mobile platform, Microsoft has segregated the core in-box Windows 10 apps from the platform, and that system seems to work. Apps are updated, often literally, every day. And while I’m sure there are issues from time to time, issues with a single app will never be as serious or damaging as core OS issues. A broken app won’t trigger a blue screen or cause your PC to stop booting correctly.

Constant app updating is only a problem in low- or expensive bandwidth situations, as is the case with mobile devices too. But Windows is at least sophisticated enough to handle that issue seamlessly. For the most part, that part of the rapid release promise seems to be working out.

So what’s the solution?

Windows as a Service can only really work under two conditions that do not exist today: There really needs to be a single version of Windows 10 that is regularly updated. And that version of Windows 10 needs to be serviced with updates that are in fact reliable.

Neither is easily achieved: I get the feeling that the proliferation of supported Windows 10 versions was driven by enterprise customers that were nervous about being regularly updated beyond their control. And Microsoft is intent on defending its reliability record and hasn’t admitted that it has endemic problems. That these two issues feed each other is, of course, not coincidental.

But the underlying issue is simple enough to identify: Microsoft can try to update Windows 10 “as” a service, can try to pretend that this system can be updated like a mobile platform. But it’s neither. Cloud services can be updated more quickly and easily than client-side platforms specifically because they are controlled from a central location. And mobile platforms are much less complex than Windows 10, a legacy software platform with roots in the first early 1990’s release of Windows NT.

For this scheme to truly work, enterprises would need to give up control over updating, which isn’t happening. And Windows 10 would need to be stripped down to a more modern core, something we might call … Windows 10 Mobile. And I think we all know that’s not happening either.

Microsoft’s goal with Windows as a Service was pure and well-intentioned. But it may never work. And after the tough past year or so, I’m not sure how Windows will absorb this hit. The only thing worse would be continuing down the current path and pretending that it’s working.