The Enshittification of Personal Technology (Premium)

Tech journalist Corey Doctorow describes the way that services move from being free to abusing their users as “enshittification,” which is painfully accurate. It’s a process any Microsoft user will recognize—witness how previously-free Teams features are now part of the paid Teams Premium subscription—but it’s not just Microsoft, of course. We see this all over personal technology, from the ads ruining Google and Amazon search results to Netflix’s anti-customer strategy of charging extra for sharing accounts with family members.

Doctorow—whose recent book Chokepoint Capitalism: How Big Tech and Big Content Captured Creative Labor Markets and How We’ll Win Them Back is worth reading—offers more context.

“Here is how platforms die,” he writes. “First, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die.”

There are so many examples of this. Social media ranks highly here: I adopted Instagram as a way to share my love of photography with the world—as opposed to that subset of the world’s population I personally know, which is what I use Facebook for—and while it was never perfect for that use, it has since devolved into a place for videos and shopping, and it is riddled with ads and sponsored posts that hide the content I want to see.

I’m no Luddite, and I don’t want to return to the age of mix CDs, paper photo albums, DVD movies, and dumb phones. But the enshittification of personal technology is a byproduct or symptom of a larger issue in which we collectively charge forward and adopt new technologies without first pausing to consider the ramifications. AI is such an obvious example that it’s almost worthless as a discussion point. But it’s not just AI. It’s everything.

What I care most about, of course, is Windows. And I’ve been complaining about the enshittification of Windows for what feels like forever. From the slippery slope of in-product advertising that began in Windows 8 to the forced telemetry, tracking, and sponsored apps that arrived in Windows 10 to the bogus hardware requirements, functional regressions, and forced Edge usage in Windows 11, it sometimes feels like Microsoft is purposefully undermining this once-revered product. OK, not just sometimes.

I know we have alternatives. And I know that every complaint I issue is like a dog whistle for fans of Linux or the Mac, or even the iPad or Chromebooks, an opportunity to explain how their favorite platform doesn’t suffer from the problems I seem so concerned with. And that’s true. But in a classic “grass is always greener” scenario, they each suffer from their own problems, too. Is each enshittified? I don’t know them well enough to say, honestly. But each does have its own problems, or at least some inherent blockers related to workflow, app availability, or whatever, that raises the bar for moving off Windows.

Two points come to mind here. One, I don’t want to leave Windows, and I feel that I’m most productive in this environment. Two, I still prefer Windows 11 to the alternatives, even with the issues noted above. I don’t write that in a vacuum, as I regularly or semi-regularly use each of the other platforms and consider alternate futures all the time. It’s just my preference.

What I would like to see, of course, is the de-enshittification of the products and services I use, including Windows. That is, I would just like Windows to be better, not to have to stop using Windows. Thinking about what I use more broadly, I am of course open to switching where it makes sense, with the understanding that if enough of us walk away from an enshittified solution, its owners will either fix it or some other thing will become popular enough and good enough that it won’t matter. (Small example: when Pocket Casts became enshittified, I left for Castbox, but when they fixed Pocket Casts because of complaints, I went back.)

This is, of course, what the people leaving Twitter for Mastodon are hoping to achieve. And I get that, vaguely, though I haven’t had any issues with Twitter at all, even under Elon Musk. And Musk’s insanity certainly isn’t enough to get me to leave Twitter. If a CEO I viscerally cannot stand is the bar, I would have to drop all of the Big Tech products and services I use. These people and the companies they run are all terrible.

Bringing it back to Windows, there are third-party utilities that can improve the experience. There are solutions like NextDNS that can stop the tracking. There are ways forward. I don’t take advantage of these things for the most part because part of my responsibility in writing about Microsoft and Windows professionally is that I need to have the same experience everyone else does so we can discuss them accurately. But these things bother me. I would like this product to be better. And I would prefer for that to come from Microsoft.

That’s a fool’s dream, of course.

Indeed, when you look back on the Corey Doctorow quote above and apply it to Windows, you can see how it parallels the history of this product perfectly. “First, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die.”

We’re at the point in history where Microsoft is abusing its business customers with Windows. In its bid to convince business customers to let it service Windows as it wishes, the software giant is trying to change the support terms that have been in place for decades while retaining the per-PC/per-user licensing fees that arrived at the same time. I don’t really think about this stuff too much because I’m more concerned with the individuals who use Windows than the businesses. But that’s happening too.

Today, Windows 11 is free but not free, because nothing that is free is truly free. We pay for Windows 11 in ways that are annoying, that distract us from the work we’re trying to do, that try to convince us to pay for other things, other subscriptions that are tangential to the thing we’re actually using. And it’s only going to get worse.

And that’s the toughest thing of all. It’s only going to get worse.