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 (Likewise, the September release has been replaced by a release in the vaguer second half of the year.)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 woul...