2019: The Year in Windows 10 (Premium)

How does one even explain what happened to Windows 10 in 2019? It was the year everything changed. At least some of those changes will persist into 2020 and beyond. But thanks to Microsoft’s cone of silence—the firm’s inability to communicate effectively certainly didn’t change this year—it’s not clear whether some of the more positive changes will continue forward.

I’ll try to explain this as clearly as possible. It will not be easy.

Traditionally, Microsoft has issued two Windows 10 feature updates—i.e., two major new Windows version upgrades—each year. Those feature updates were typically completed in March and September and were then released to the public in April and October. And so the resulting Windows 10 versions bore version numbers, like 1809, 1903, and so on, that reflected when they were completed; Windows 10 version 1903, for example, would be completed in March (03) 2019 (19).

This rarely happened on schedule, of course. Both of the feature updates that Microsoft released in 2018 were quality and reliability disasters and each was delayed in some way; Windows 10 version 1803 was quietly delayed for over a month when Microsoft found issues at the last minute and version 1809 was even worse: Microsoft actually had to recall that update and it didn’t reissue it until almost two months later, in December 2018.

But there was another complication to the schedule: In 2018, Microsoft also let Windows leader Terry Myerson go, and in the wake of his departure, the Windows team was dissolved. Responsibility for kernel and core development fell to Jason Zander’s Azure team. And a dwindling team focused on new user experiences, led by Rajesh Jha, which is part of the broader Microsoft 365 business.

Windows fans were right to be worried about the impact of these organizational changes on their favorite tech product, and we saw the results in 2019. With no direct leadership, and no representation on Microsoft’s Senior Leadership Team (SLT), Windows 10 was forced to conform to the Azure release schedule and codenaming scheme. This isn’t all bad: Instead of basically promising a March release each year, for example, Microsoft now commits only to delivering a feature update in the first half of the year. (Likewise, the September release has been replaced by a release in the vaguer second half of the year.) Thus, Windows 10 version 1909 was called 19H2 during development, though it switched to 1909 for release because version numbers can literally only contain numbers.

Confused? We’re just getting started.

To date, Microsoft has issued public betas for each Windows 10 version through the Windows Insider Program, which is responsible for marketing and community building, not engineering. This group took the internal beta seeding program, which uses access “rings” to distribute Windows builds, and extended it for the public. In the beginning, it was very simple: There was a Fast ring that would see new builds of the next Windows 10 version roughly once a week. And a Slow ring that would see more stable builds roughly once every six weeks.

The Insider Program was never able to keep to that schedule, and over time, things got more complex. They added a Release Preview ring for those who only wanted to test the new in-box app versions. And then a Skip Ahead option for Fast ring testers who wanted to “skip ahead” to the next-next version of Windows 10 late in the development of the next version, when that one was basically done.

Then 2019 happened.

In February 2019, with development of Windows 10 version 1903 winding down, Microsoft did something unprecedented: Instead of switching Switch Ahead testers to Windows 10 version 19H2, as would be normal, it switched Skip Ahead and Fast ring testers to Windows 10 version 20H1, which wasn’t set for release until over a year from then. The Insider program vaguely admitted that Windows 10 version 19H2 was still happening, but that it would explain that later.

And it was later. Months later. In very late June 2019, Microsoft finally opened up Windows 10 version 19H2 testing … to those in the Slow ring. It would eventually arrive as Windows 10 version 1909 … in November 2019, about a month after the normal release timeframe.

But wait, there’s more.

With Windows 10 version 20H1 being tested so early, Insiders naturally assumed that it would be a major, major release: After all, Microsoft was testing it for double the normal amount of time. But it’s not. Windows 10 version 20H1, despite all the testing time, is a very minor release for a feature update. And while there are certainly new features, they are all so minor that most Windows 10 users will never even notice that anything changed. (My theory here is that 20H1 was really about underlying/core/kernel changes related to Windows 10X, the specialty version of the product aimed at dual-screen portable PCs that will arrive in 2020.)

And what about 19H2?

That release of Windows 10 is even less substantial than 20H1, and Microsoft tested and released it as a cumulative update, the type of updates that Windows 10 users install one to three times per month. It only includes a few tiny and barely noticeable changes, and is, in effect, really just Windows 10 version 1903 with a different name.

What’s interesting about 19H2, of course, is that installing this “feature update” is much quicker and less error-prone than installing a real feature update. The whole process takes just a couple of minutes, vs. 45 minutes to one hour for a real feature update. So the success rate and, presumably, the user satisfaction are both much higher than is typical for a feature update. In other words, Microsoft finally figured out a way to solve its feature update quality and reliability issues: It just pretended that a smaller and simpler cumulative update was a feature update.

Stepping back for a moment, it’s worth mentioning, too, that Windows 10 version 1903 rolled out very slowly because of the quality and reliability issues that its predecessor experienced the previous year. It wasn’t OK’ed for broad distribution until late summer, months later than usual. But because 1903 and 1909 are literally the same product, they are serviced with the same patches, ensuring better quality and reliability for their respective lifecycles. Windows 10 version 1909 is essentially the long-term-servicing version of 1903.

During all this, Microsoft also changed how the Insider program worked: It got rid of the Skip Ahead option. And as of now, both the Fast ring and Slow ring are testing Windows 10 version 20H1, whose development is now winding down, months ahead of the normal schedule. It turns out we weren’t going to test 20H1 for a year after all. But 20H1 will be marketed as Windows 10 version 2004. Yep. They expect to release it to users by or in April, many months after development ceases.

What does this mean?

My expectation is that this new H1/H2 testing scheme continues. And that Microsoft will continue releasing each feature update months after testing concludes; this will give it time to find more bugs and issue several cumulative updates before general availability. The end result should be better quality and reliability and, hopefully, a permanent end to the self-inflicted problems it experienced in 2018.

The question, of course, is whether Microsoft continues with the major/minor release cadence we saw in 2019. That is, we know that Windows 10 version 20H1/2004 is a major release, i.e. a “real” feature update. But what about 20H2? Will Microsoft return to its old way of doing things and make that a “real” feature update too? Or will it go the 19H2 route and be a smaller, simpler cumulative update that is marketed, again, as a feature update?

Like most in the community, I am hoping for the latter. And that we find out what’s happening before the end of the month. After all, Windows 10 20H1 development is already done. So the next Fast ring build could be, should be, a 20H2 build. We’re on the precipice, wondering which way Microsoft will go.

And that, folks, is what it was like to be a Windows fan in 2019. Uncertain of the future.