Redmond, You Have a Problem. A Quality Problem (Premium)

One of the issues with being a Windows enthusiast is watching Microsoft lose interest in this important platform. This isn’t theoretical. As Microsoft’s focus shifted to businesses, enterprises, cloud computing, and then AI in turn, Windows fell ever further from the center of the company’s attention and ambitions. The net result of this lack of focus is diminishing quality with each subsequent Windows version. And now that Windows 11 version 24H2 is being broadly deployed to the public, you can see that this release represents a new nadir for product quality.

I recently spoke at tech event in Dallas, the first I’ve done so since before the pandemic, that ever-looming moment that divides the “before times” with today for all of us. In preparing for this talk, several themes emerged, and while I was deciding which to focus on, I finally reached out to Mary Jo, who had spoken at the same conference a year earlier. And I was surprised to discover that our talks, created separately and in isolation, had major crossovers. One of them is what we now call enshittification, but in her talk a year ago, Mary Jo described it as “where Microsoft’s needs and its customers’ needs diverge.”

A few readers seem to dislike the term enshittification, but it’s too perfect to ignore. The word instantly communicates its meaning. Once you understand what it is, you see it everywhere. And in our little world of personal technology, the problem is particularly acute. For consumers at large, Netflix and Spotify are perhaps the best examples, the perfect examples. But in my even littler world, this subclass of personal technology that still cares very much about the PC, there’s an even better–OK, worse–example.

Windows.

That Windows is enshittified is not up for debate. But this isn’t even new. It started with Windows 8, over 10 years ago, when Microsoft chased the Apple iPhone and iPad dragon, ignoring the needs of its one billion-plus installed base, delivering a one-way dead-end street in the form of touch-first mobile user interfaces that statistically no customers wanted, needed, or owned devices capable of using them effectively. There were other examples–Windows 8 was when the first in-box advertisements appeared in this platform, for example. But Windows 8 overall is the very definition of Microsoft putting its strategic needs over the needs of paying customers, and the start of a horrible trend that only escalated in the coming years.

The release of Windows 8 is important in the history of Windows because it also marks another dividing line between the “before times” and today. Windows 8 was the last major release of the product in which the entire company rallied around the release because Windows was still core to Microsoft. Not the center, but one of its most important products. But it was the wrong answer at the wrong time, and Microsoft could not have turned its back on Windows more obviously than it did at the time. Steve Ballmer handed this product line over to the Windows Phone team–seriously, think about that for a second–and the rest of the company simply ignored Windows and its silly app frameworks, most crucially Office. It was over: The iPhone may have been the Asteroid that killed the Windows dinosaur, as I once wrote, but Windows 8 delivered the curb-stomping final blow.

What we didn’t know at the time is that then-new Windows chief Terry Myerson was given an edict by then-new CEO Satya Nadella, a directive that was also issued to all of Microsoft’s other product groups: Windows had to make sense in the then cloud-focused Microsoft. Some product lines–Windows Server, Office–made this transition seamlessly. But Windows was a problem.

Customers had long dreaded what they felt was the inevitable shift from Windows as a paid product to Windows as a subscription product. But that was impossible: Apple had already stopped charging for OS upgrades, and after Microsoft made Windows 8 upgrades available cheaply, there was nowhere to go. Windows 10 had to be free, and so Myerson’s team had to look elsewhere for synergy. The answer was controversial and remains so today: Microsoft would update Windows 10 as if it were a cloud service, and it literally named this initiative Windows as a Service (WaaS). If it could do this reliably, it would be a win-win, ostensibly, though the rapid update cycle it envisioned was of zero interest to businesses, the biggest and most important and lucrative customer base for Windows.

The original plan was aggressive. Microsoft killed off the traditional ten-year support lifecycle in an effort to get customers to upgrade more quickly. It would release two so-called Feature Updates each year, which sounds innocuous until you realize that these updates were in fact version upgrades that Microsoft had previously delivered once every three years (Windows Vista in 2006, Windows 7 in 2009, and Windows 8 in 2012). This would be disruptive. And it was.

Worse, WaaS was incredibly unreliable. Microsoft’s plan to address the obvious–it’s literally impossible to reliably update so much legacy code on so many client machines as seamlessly as is possible with cloud services–was the Windows Insider Program, which quickly garnered millions of eager members. But the Insider Program failed spectacularly and in what should have been an obvious fashion: Few of these were interested in engaging with Microsoft, most just joined to get free and early access to new Windows features. The efficacy of the feedback cycle was shown in the problems that each Feature Update had on release.

WaaS failed and, sadly, Myerson failed, with Windows 10 taking much longer than expected to reach the usage volume it needed to compete with Android and iPhone. So Myerson was out, and after a bizarre period in which Windows had no direct leadership and no representation on Nadella’s Senior Leadership Team (SLT), things somehow got even worse. Inside the team that built Windows 7 and 8, the team responsible for Windows Phone, the team that later made Windows 10, was deridingly called “the B-team” for obvious reasons. But for the next Windows release, Microsoft would introduce a new low, what I called “the C-team,” also for obvious reasons.

This was when we got Windows 11 and Panos Panay, a charismatic-less surface-level (pardon the pun) lightweight who did for Windows what the long-forgotten Windows Mobile 6.5 did for that platform: Instead doing deep engineering work in Windows, that team simply replaced the most commonly used parts of the user interface, introducing new reliability issues and more functional regressions than I care to remember. It began with so many lies, the biggest being that Microsoft would relax its two-per-year Feature Update schedule and release just a single Feature Update each year.

This was greeted with cheers. But before those cheers died down, a harsh new reality emerged: Yes, there would be just one Feature Update each year. But Microsoft reserved the right to deliver new features each month, via cumulative updates that even its business customers could not avoid. This evolution–really, escalation–of WaaS was rebranded as “continuous innovation,” a term so laughably oxymoronic–it reminds me of equally ludicrous terms like “planned serendipity”–I could almost cry. The result is well-understood. Microsoft over-promised and under-delivered with Windows 11. Adoption rates hit an all-time low for the modern Windows era. And Microsoft, inexplicably, turned up the crank on delivering new Windows features. Every. Single. F$%#ing month.

It got chaotic and unpredictable. Because the Insider Program had long since ceased to be in any way useful, Microsoft rejiggered the various channels that system provided multiple times and then ignored it almost entirely, delivering new features in stable–now called the “General Availability channel”–without any testing of any kind. It even escalated beyond the new features once per month schedule by introducing new features in stable twice per month, once at the normal and long-lived Patch Tuesday milestone–the second Tuesday of the month, or the Tuesday of what Microsoft calls Week B–and once on the Tuesday or Week D, when it delivers so-called preview updates.

Preview updates are optional, so Microsoft also introduced a new toggle in Windows Update that uses the same dark patterns we see in Windows 11 privacy settings and Microsoft Edge: “Get the latest updates as soon as they’re available” makes something that Microsoft wants seem like something the customer might want. The net result being that customers who do enable this toggle will get new features twice per month–Every. Two. F$%#. Weeks–some of which were never tested even for a second in the Insider Programs, others that were very briefly tested, sometimes literally for as little as two or three days. Which is the same thing as not being tested, of course.

There was a brief moment when it seemed that Windows would rebound, would bounce back from the quality nadir it had hit with a thud: A bit over a year ago, Panay abruptly left Microsoft. He was immediately replaced by 20+ year Microsoft veteran Pavan Davuluri, an affable and well-spoken man who might accurately be described as the anti-Panay thanks to his confident public presence and computer science background.

Inexplicably, things have gotten even worse under Davuluri. I’ve written many, many words about this escalating chaos, but the next several months were an unprecedented mess. Under Davuluri, Microsoft shipped new AI functionality like Copilot early via a mandatory monthly cumulative update that customers could not avoid, meeting Nadella’s new company-wide requirement that each product team must focus now on AI. (Or is it security? I’m having trouble remembering.) Originally planned for last year’s (temporarily optional) Feature Update (23H2), these features were then changed repeatedly post-released, with Copilot moving around the Windows Taskbar like a Mexican jumping bean over the next several months. 23H2 became an enablement package, and Windows 11 versions 22H2 and 23H2 were the same product, functionality, with just slightly different names. So much for that formal support lifecycle.

Then it got worse yet again, and with Windows 11 version 24H2, we’ve reached a new, previously unimaginable low. 24H2 was released in two waves, one for Qualcomm Snapdragon Elite X-based Copilot+ PCs in June, and one for mainstream x86 PCs in October. Microsoft didn’t document 24H2 monthly cumulative updates (or Week D preview updates) on its Support website, as it did for 22H2 and 23H2, until the October release, pretending it wasn’t available but delivering new features twice each month regardless (and aligning the feature set with 22H2 and 23H3 for some reason). There was the Recall disaster, perhaps the most egregious example of Microsoft releasing not just a feature, but a major new platform feature, in Windows with literally zero testing of any kind. Or at least trying to do so. As we all know, Recall crashed and burned even more quickly than Windows 8, and as of this writing, we still don’t have the feature, even in preview. That happens, allegedly, later this month.

Mixed in with this messy stew, Microsoft added Copilot+ PC capabilities, but only for Windows 11 on Arm-based Copilot+ PCs, not those with Intel and AMD chips. Intel and AMD responded by meeting the spec with new chips, but Microsoft refused to publicly state whether they’d be granted access to those features. When it finally did admit they would be allowed in, it qualified the news by saying that this access would come later. After 24H2. Which was already shipping on new PCs based on those chipsets. As of this writing, Intel- and AMD-based PCs with qualifying Copilot+ PC specifications still don’t have those features, even in preview. That happens, allegedly, next month.

But Windows 11 version 24H2 finally arrived in October, or at least the Second Coming of 24H2 arrived. And this release–this re-release, or mulligan–is why I’m sitting there today, writing this, and dismissing the Copilot app window that keeps appearing unwanted as my clumsy fingers inadvertently tap the unnecessary and unwanted Copilot key that graces–ruins–every new PC these days. This is astonishing to me. Despite shipping 24H2 to the public on new Copilot+ PCs in June, despite 24H2 being functionally identical to its predecessor, and despite several months of additional testing in the Insider Program across multiple channels, 24H2 is no bueno. There’s something wrong.

Well, not something. It’s many things.

Horror stories of the problems with Windows 11 version 24H2 abound. There are so many bugs, so many reliability issues. This may be the lowest-quality release of Windows in history. And yes, I remember Windows Me. Stop bullying Windows Me.

The biggest story involves 8.63 GB of curiously specific missing disk space after the 24H2 update, a so-called “reporting error” that Microsoft finally acknowledged and will soon fix. Customers with Western Digital SSDs are getting Blue Screens all over the place. The vanishing mouse cursor issue I first noticed over the summer is now a widespread issue; it turns out that 24H2 uses the wrong default text insertion (“I-beam”) cursor. Some users reporting losing Internet access after the update. And the System File Checker, a command line tool, will detect bogus corrupt files and then “fix” them, a time-consuming process, after the 24H2 upgrade.

On and on it goes. Windows 11 version 24H2 was (re)released just two weeks ago. And all hell has broken loose. Microsoft is now “pausing” the release of certain new features that would otherwise have shipped in stable in November to address some concerns. But that’s like closing the Windows Update barn doors after the quality horse has run away.

It almost makes one pine for the brief, simple-stupid days of Panos Panay. It absolutely makes me wish Terry had never left. But I’m also faced with a curious paradox. What I really want, what Windows really needs, is true leadership. A person with a vision, a person who actually cares about the product and lives and breathes it every day. And for that, I have to go back to—Godammit, help me get through this–Steven Sinofsky. And an era–long gone and long forgotten–in which Windows mattered. Under Sinofsky, Windows mattered. And Windows was, if not the focus at Microsoft, a major focus.

I miss those days and badly. I used to joke about the inmates running the asylum. And then about children running the asylum. About “bring your child to work” day for the Windows team. I even predicted, jokingly, the 24H2 disaster.

But this is no joke. Windows is the joke. And I am F$%# tired of that being true.