When You Use Windows 11, Are You the Product? (Premium)

Former Microsoft engineer Dave Plummer posted an interesting video this past week about Microsoft's shift to free Windows upgrades. He explains why he thinks this happened--declining PC sales, the Windows 8 backlash, Linux, and Apple's push to make macOS upgrades free are key among them--and what he sees as the "hidden costs" of this change: Forced telemetry, advertising, and a shift to subscriptions.

Sound familiar?

It should. We've been discussing these topics here since, well, the beginning. And while Plummer doesn't provide any new information here--not for the first time, unfortunately--his videos are so widely viewed that the issues we've all been debating for years likely feel new for much of his audience. And to be fair, there is a discussion to be had on this topic. Windows is always top of mind (for me), and in this era of enshittification, I feel the quality problems in Windows 11 in an almost visceral way. These problems so serious that I've made major shifts to non-Microsoft solutions for cloud storage and writing that would have been inconceivable just a few years ago.

But before diving into this further, we need to discuss Dave Plummer.
?‍♂️ The problem with Plummer
As I wrote recently in Ask Paul, I subscribe to Dave's channel and watch every video he produces. He's interesting, well-informed, and technical, and thanks to his history at Microsoft, he is by definition someone I need to pay attention to. As the author of a book about the history of Windows and someone who has been covering this operating system professionally for over 30 years, I was curious--OK, I was excited--when he posted a video about Longhorn recently, assuming he'd have some nuggets of new information that even I hadn't heard before. His epic interview with NT architect David Cutler is essentially viewing/listening, after all. But there was no new info.

This was surprising and disappointing. I realized while watching it--and then rewatching it--that a key reason was that Plummer wasn't actually at Microsoft for most of that saga. He went on sabbatical before Microsoft revealed Longhorn to the world at PDC 2003, and then he left the company for good instead of returning. He wasn't there for Longhorn, and he didn't have any internal information that might have put that video over the top.

Well, Plummer wasn't at Microsoft for Windows 10 or 11 either. And while he must still know a handful of people still working at the software giant, and possibly even some involved with Windows, I had better and more contacts within Windows and Microsoft during this time than he did. And I know a lot about the internal machinations that led to key strategy decisions with Windows 10, in particular. I was very close with Terry Myerson, for example, and most obviously.

This isn't a contest. As noted, I'm a fan of Plummer and his YouTube channel, I respect him on a technical level, and I look forward to every video. But as he gets into topics that I'm...