The Next Windows 11 Update (Premium)

There’s a lot to talk about in the wake of today’s Microsoft Special Event, but I’d like to first hit on something near and dear to my heart.

I am referring, of course, to Windows.

If you follow me in any way—reading Thurrott.com, watching Windows Weekly, whatever—you have surely observed my frustration with the ever-changing ways in which Microsoft updates Windows in this modern era. And today’s event … triggered something.

First, the history.

These changes started over a decade ago, when Steve Sinofsky was forced out of Microsoft in late 2012. Because Windows 8 was so reviled by Microsoft’s customers, it halted the normal updating cadence and entered what it called a “rapid release cycle,” whereby it would quickly fix everything that was wrong with the product via a succession of updates starting with Windows 8.1.

Windows 8.1 was unique for two reasons. It was the first—and, as it turns out, only—Windows update delivered via the Windows Store, not Windows Update. For some reason. And … it was free. To be clear, Windows 8.1 was an upgrade for Windows 8 only, but it also wasn’t a service pack. It was a full Windows release. And it was free.

After Windows 8.1, things got weird for a different but familiar reason. There were at least two meaningful updates to Windows 8.1, each of which further walked back the mistakes of Windows 8, and each of which was delivered through Windows Update. And each was named differently. Because Microsoft.

With Windows 10, Microsoft introduced further changes. It would ship three major releases of this system each year, but then quickly changed the cadence to twice per year. It would be a free upgrade, but not just for one previous version: Those with Windows 7, Windows 8.x (any version), or even Windows Phone 8.x would get it for free. And the update lifecycle, which had long been ten years with five years of mainstream support and five years of extended support, shifted to something vague that was never explained: It was supported for “the lifetime of the device.” Whatever that meant.

Over Windows 10’s active years, Microsoft shifted its updating strategy repeatedly. At first, both releases each year were major updates, but after some failed to live up to that term, it changed to a major/minor schedule where it shipped a major release in the Fall (H2) and a minor release in the Spring (H1). The naming silliness continued, with an Anniversary update, a series of Creator Update releases, and then month/year releases (October 2108 Update, etc.).

The only hint we ever got about that “lifetime of the device” line came in late 2015 when Microsoft bungled the release of the Skylake-based Surface Pro 4 and Surface Book, and incorrectly placed the blame on Intel. In retribution—Intel refused to fix the problems, as they were Microsoft’s responsibility—Microsoft stopped supporting older Intel chipsets with Windows 10, suddenly triggering a customer support crisis when millions of innocent users discovered that they would never again be allowed to upgrade to a new OS version. For some reason.

And then there’s Windows 11.

My God, Windows 11. We cheered at first when we were told that Microsoft would scale back its update schedule and would now only ship one upgrade a year. And then we worried when were told that it reserved the right to update Windows 11 whenever it wanted. Sure, there would be only one major upgrade—called a Feature Update because naming is hard—but there could in fact be multiple feature updates (small f, small u) between those upgrades.

And there were. At first, this was somewhat understandable, as the initial release of Windows 11 was buggy, missing promised features, and full of functional regressions compared to Windows 10. But then it got weird. By the time the second release of Windows 11, called 22H2 came due, Microsoft silently shifted to a new and undocumented strategy by which it released new features almost every month (called Moments internally), released preview updates of those new features beforehand (on two different schedules, but now it’s the Tuesday of the Week D each month), and sometimes even introduced new features without first testing them in the Insider Program. (Which by then was in its own feature release schedule mess, with A/B testing, new features debuting out of order in various channels, and other issues.)

I spent much of this past year trying to figure out what Microsoft was doing, which was hard given that it changed almost monthly. And then, unexpectedly, Microsoft actually documented what it was doing with the quiet release of a Windows updating strategy whitepaper. Retroactively, Microsoft tried to make sense of the past 8 years of nonsense (this covered Windows 10 and 11 only, as Windows 8 was out of support by then).

And I breathed a sigh of relief. Obviously, I knew that things could change again, it’s Microsoft. But with 23H2, the third version of Windows 11, due in the next few months, I figured we were out of the woods.

Not exactly.

That same week, Microsoft revealed that 23H2 would be delivered as an enablement package, which is the system it shifted to with Windows 10 after each update had become so minor as to not warrant any publicity. This meant that 23H2 would not reset the compatibility requirements, which in the past had required rolling out release slowly over time to ensure there were no issues. And so the theory was that everyone running 22H2 would just get 23H2, with no waiting. If you ran 22H2, you were compatible with 23H2. It’s all the same source code base, meaning 23H2 isn’t a new branch.

That sounded good. And looking both at the past and at the calendar, I surmised that Microsoft would deliver the preview version of Windows 11 version 23H2 on Tuesday, September 26. And that the public, non-optional version would arrive on Tuesday, October 10. Because that was the schedule.

And then we came to New York for the Microsoft Special Event today. And for all the interesting AI functionality coming across Bing, Edge, Microsoft 365, and Windows, there was one thing that really stuck in my brain during the presentation: Yusuf Mehdi, standing on stage, announced “a new Windows 11 release” would arrive on September 26. He called it “the most ambitious update to Windows 11 yet.”

So there it was. He had just confirmed the schedule I surmised. This had to be Windows 11 version 23H2.

And then confusion set in.

After the presentation, Microsoft told us that this release was not 23H2, it was instead a monthly update for Windows 11 22H2. 23H2, they said, would come “later.” Whatever that meant. And so asked everyone we knew who was there from the Windows team, and we got different answers from them all. The only commonalities are that they clearly don’t like using the term 23H2 and want this thing to have a friendlier public-facing name.

So we turned to the documentation. And the announcement refers to this thing by multiple names, blurring things even further: “a free update to Windows 11,” “the next Windows 11 update,” “the new Windows 11 update,” and “the latest update for Windows 11.” Seriously.

I was convinced my schedule was right and that Microsoft’s inability to communicate and name things properly had once again gotten in the way. And then, finally, came the confirmation. Two and a half hours after the presentation, Microsoft posted a Windows IT Pro Blog post describing this release. And I am happy to report that I was right. This is 23H2. (Not happy for me, but happy that the schedule still makes sense, naming be damned.)

“Copilot in Windows will start to roll out in September 2023 optional non-security update for Windows 11 version 22H2,” Microsoft’s Harjit Dhaliwal writes.

To be clear, this describes the preview version of 23H2, as this is exactly how and when this release will roll out, and because the contents of this update constitute version 23H2. An “optional non-security update” is an update preview.

“It [Copilot] will later be included in Windows 11 version 23H2, the annual feature update for Window 11, which will be released in Q4 of this calendar year.”

If Microsoft is on schedule, that means that 23H2 will ship on October 10, as I predicted. However, that vague schedule also suggests that it could happen later. Given how buggy some of this is—in particular, File Explorer—that is perhaps not surprising. But if true, that means that Microsoft is once again screwing with the updating schedule.

And you know what? Screw it. Of course they are. Maybe it’s time I just gave up on certainty and accepted the new way of doing things, which always changes and has been changing for a long time. It would certainly be healthier.