Security and upselling are orthogonal; I can make a secure operating system that doesn’t notify the user of OneDrive, iCloud, and other services.

Things get more nuanced when we talk about other types of notifications and about whether updates should be automatic or always require a user’s explicit consent. I personally believe that a key tenet of personal computing is that the owner of the computer, not the hardware or software vendor, should have full control over the hardware and software on the computer. This control is undermined when systems are designed in ways to give users less control. There may be legitimate security benefits to mandatory automatic updates, for example, but there are risks, such as buggy updates leading to broken installations or even lost data, and there’s also having to deal with unwanted UI/UX changes.

As a power user, developer, and researcher, I want control over my computing environment. Unfortunately Windows and macOS have been trending toward more paternalism, more nagging, and more upselling. Thankfully Linux exists, but at the cost of needing to switch away from convenient proprietary software tools like Microsoft Office. I can do without Word or Excel, but PowerPoint is what keeps me on Office (I’ve tried LibreOffice and the Beamer LaTeX template). I’m also concerned about hardware getting increasingly locked down, which will hurt Linux.

I had the same reading, it sounded like Windows is worse now than Windows 95, which would be a hot take indeed. But it seems the intent was purely on these nagging aspects which have definitely gotten worse.

It might be easier to swallow the message focusing on Windows 8+ when it really jumped the shark. Windows 7 was a pretty good OS holistically I think even if there are aspects lost compared to the pure simplicity of those really old ones.