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...

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