Deceptive (Premium)

Now that we’re in year two of the enshittification era, Big Tech is expanding its efforts to coerce or force customers down paths that benefit it more than us. This is a quick story describing one of the more common and subtle examples of this coercion, via the use of purposefully misleading language.

This may seem like a small issue, but believing so says a lot about the scope of enshittification: We live in a world where deceiving customers can somehow be brushed off as table stakes. But deceptive language, like deceptive user interfaces, is just the most obvious type of dark pattern, a practice the U.S. government says, “will not be tolerated.”

As if.

Microsoft users tolerate this behavior on an almost daily basis. Consider the Microsoft Edge on-boarding process I document in the Set Up Microsoft Edge Correctly … Whether You Use It Or Not chapter of the Windows 11 Field Guide. This simple, four page initial setup includes a “Help us make Microsoft experiences more useful to you” step, pre-selected for you, that pretends to offer a superior configuration for you, the user, but is designed solely to advance Microsoft’s strategies by exposing you to more online tracking, data harvesting, and Microsoft advertising.

That one is a classic. But here’s another example of the same behavior.

I pay for Xbox Game Pass Ultimate, the most expensive tier of Microsoft’s gaming subscriptions. This subscription costs $16.99 per month, is difficult to prepay over multiple months (which will/should save you money over the long term), and, among other things, it provides members with access to the Xbox console, PC, and Xbox Cloud Gaming (streaming) libraries.

Many new PCs offer buyers three months of Xbox Game Pass Ultimate for free as a perk: This, like the pre-bundled Microsoft 365 apps, is one of many ways in which Microsoft’s partnerships with PC makers surfaces, and it’s difficult to argue with this attempted upsell. After all, Microsoft and the PC makers are all trying to make a buck here, or, more correctly, trying to earn more per user per month/year. This is one of the least offensive attempts, in my opinion.

As noted, I already pay for Xbox Game Pass Ultimate. So it’s reasonable to assume that this offer doesn’t apply to me. As it turns out, however, it does: Existing members can step through the process of accepting this offer and add three months to their subscription. And so this morning, I saw this offer and decided to go for it.

There’s just one gotcha: During the process, Microsoft informs you that agreeing to the offer will enable recurring billing so that the subscription will auto-renew each month after the current period expires. My Xbox Game Pass Ultimate subscription was paid up through May 2025 at the time I accepted this offer, and I had disabled recurring billing. No problem, I actually paid attention while I accepted the offer, as many do not, and so I immediately opened my web browser and navigated to the Microsoft account website to see what had changed. Note that Microsoft did not provide a link to do this.

What I discovered, right there on the site’s home page, was that my subscription had been extended out to August 2025 and recurring billing was enabled. As expected.

So the next step was to disable recurring billing. So, I clicked the “Turn off recurring billing link” next to that subscription and was greeted by this purposefully confusing screen:

This is clearly designed to make you believe that continuing with this will result in your Xbox Game Pass Ultimate subscription being canceled. Which many would believe could result in them losing the three free months they just added. With the understanding that few customers would have found this site to begin with, it’s likely that some percentage that did would decide to hold off. Just in case. And, in Microsoft’s view, you will hopefully forget about it entirely.

But I knew what I was doing. So I scrolled down past the (acceptable) other offers–again, this is a business, not a charity, and not all efforts to make more money are inherently evil–so that I could find the “Turn off recurring billing” button nestled between bigger offer-based blocks.

I knew what to expect, but the next screen is nonetheless chilling and is, again, purposefully deceptive.

This seems to indicate that you just closed the subscription. But small text in a light font color reveals the truth: My subscription is still enabled through August 2025. The only change, despite the scares, is that I have indeed disabled recurring billing.

(As an aside, I also received an email when I first accepted this offer. It reads, “Per your request, your Xbox Game Pass Ultimate subscription has been updated to recurring billing, which will start on Wednesday, August 06, 2025 at USD 16.99 plus applicable taxes.” This was not my request, of course, it was a requirement of accepting the offer. But at least Microsoft notified me. And that email does provide a link that goes to the appropriate page on the Microsoft account website.)

To be clear, this isn’t the most egregious example of this tactic in the Microsoft space. But that’s the point: All over the ecosystem, we’re being beaten down with more and more of these types of incursions, like death by a thousand cuts. And the overreaching goal is the same as those of junk mail senders back in the day or online-based spam today: To overwhelm people in the hopes that some won’t pay attention and will cough up money for a service they don’t need and won’t use.

And to be clear, it’s not just Microsoft, of course. But Microsoft is the focus here, and it’s the world in which I see this type of problem most often. It provides a stark contrast to the feel-good vibes you get from events like last week’s Copilot+ PC launch and Build 2024. And yet is as core to that business as the products and services it announced then. It’s important for us as individuals and consumers to be mindful of this.