Microsoft’s Windows Update system is broken. Will it ever be fixed?

It’s a bad sign when companies answer complaints and concerns with corporate doublespeak.

virtual update button hovers over a keyboard
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For many years, Microsoft has struggled to get the way it updates Windows right — and mostly got it wrong. But a month ago, I wrote about how Microsoft finally got a piece of it right, by giving people control over whether to install the twice-annual feature updates, such as the recent Windows 10 May 2019 Update.

Boy, was I ever off-target. Over the past few weeks, Microsoft has done little more than sow confusion about how and when Windows will be updated. It did this by issuing Orwellian statements and putting out a preview release schedule whose logic is undiscernible.

Clearly, Microsoft’s system for updating Windows is as broken as broken can be. And there are no signs it will ever be fixed.

To see why, you need to understand a bit about how Microsoft tests its twice-a-year feature updates, like the recent May 2019 Windows Update. People who want to test the updates before they’re released can join the Windows Insider program, which lets them download preview versions for months leading up to the update. In return for being essentially guinea pigs, these businesses and consumers get to see each step in building the next iteration of Windows, which can help them prepare for it.

There are various “rings” Insiders can sign up for: the Fast ring, which installs preview updates the moment they’re publicly released; the Slow ring, which installs them later, after they’ve been tested a bit; and the Release Preview ring, which installs them only after they’re essentially fully tested. There’s also a “Skip Ahead” program that lets an Insider skip an entire Windows version to the next one beyond.

Back in February, while Microsoft was testing the May 2019 Windows Update, it announced it was releasing an early Windows Preview build into Skip Ahead. But instead of releasing a build that would come out in the fall of 2019 (code-named 19H2, for being released in the second half of 2019), it was releasing one that was two versions ahead, due in the spring of 2020 (code-named 20H1, for the first half of 2020). (Until then, Microsoft had only released into Skip Ahead builds one release ahead, not two releases ahead.)

Microsoft explained in its post: “Some things we are working on in 20H1 require a longer lead time. We will begin releasing 19H2 bits to Insiders later this spring.”

It was certainly confusing that Microsoft was publicly testing a build not due for more than a year, while not testing one due out in not much more than six months. For enterprises and individuals that need to prepare for any Windows 10 update, this testing sequence made no sense. Why should they be preparing for 20H1 when they hadn’t even seen 19H2? At least they were promised 19H2’s first builds in the spring, at which point a more normal sequence should be re-established. They would then know whether the next version of Windows 10 would bring a lot of new features, or be not much more than a rollup of minor changes.

But the spring came and the spring went. Silence from Microsoft about 19H2. The 20H1 builds kept coming, but no 19H2 builds were released. So people started asking Microsoft spokesperson Brandon LeBlanc on Twitter why no builds had been released in the spring as promised. His Twitter answer, in part: “Our definition of ‘spring’ doesn’t necessarily match to exactly when spring ends and summer begins. It’ll happen when we’re ready.”

It was an answer reminiscent of George Orwell’s critique of the abasement of language by bureaucracies. In his novel 1984, Orwell put Newspeak in the mouths of government bureaucrats, but it was just as arrogant and disorienting coming from this corporate spokesperson. How different is “Spring is when we say it is” from Big Brother’s “Freedom is slavery”?

Well, we now know Microsoft’s definition of spring: July 1, when it finally released the first 19H2 build. Maybe the Insiders, Microsoft’s unpaid beta-testers, could make that work — if Microsoft hadn’t chosen that moment to suck all the logic out of its preview release schedule. It released 19H2 into the Slow ring, and then moved 20H1 into the Fast ring. That means that people who were expecting to test the next version of Windows in the Fast ring would in fact be testing a version of Windows not due until approximately a year from now. Only Slow ring testers would get a preview of the Windows version due this fall.

Confused yet? You should be. And it only gets worse. The 19H2 version of Windows due this fall won’t be installed the way such twice-a-year updates have long been installed. It will be installed like a normal Windows monthly update. With no significant new features, it will be little more than what Microsoft used to call a service pack, which rolls up a number of minor updates together.

Microsoft tried to explain all this in a blog post, “Evolving Windows 10 servicing and quality: the next steps.” The post is full of gobbledygook, corporate doublespeak and acronyms like “CFR.” It is, to put it mildly, laughably incomprehensible.

The upshot of all this? Windows Update is broken and needs to be fixed. Microsoft owes it to its customers to be upfront about what to expect from the next versions of Windows, especially because it is using many of them — the Windows Insiders — as guinea pigs.

Enterprises in particular need to know what will be in Windows updates, so that they can decide whether and how to prepare for them. Enterprises are Microsoft’s lifeblood. Microsoft should make its update procedures logical — preferably just one significant one a year, and perhaps a second minor service pack. And it should be clear and transparent about exactly what it’s doing. That means it shouldn’t declare that July 1 is spring and it shouldn’t issue blog posts that read as if they were written by a committee made up of adherents of 1930s-style Marxism — by which I mean a combination of the Marx Brothers and Soviet apparatchiks.

Copyright © 2019 IDG Communications, Inc.

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