The Adobe Chatbot That Never Says Yes

Someone on a forum this week described trying to remove a former employee’s Adobe licence and getting stuck talking to a chatbot that typed “working on it” and then just… stopped. No confirmation, no human, no end. He sat there wondering if the thing was broken or whether that was the point.

I read that and felt something click into place, because I’ve had versions of that exact moment. Not with Adobe specifically, though god knows I’ve had my share of Creative Cloud pain managing licences for a small team years back. It’s that particular flavour of dread when a task that used to take ten seconds now requires you to convince a piece of software that you’re allowed to do the thing you’re already paying for.

Meanwhile, New York’s mayor just announced a “click-to-cancel” rule, banning subscription traps and hidden fees at the city level. California’s had something similar for a while. The reaction online split about where you’d expect: a lot of people cheering, a few pointing out that a city ordinance can’t really touch Netflix’s billing infrastructure, and one guy earnestly wondering whether NYC could enforce this against a company headquartered in California. Fair question. But here’s the thing that actually matters, and a few commenters got at it: companies comply with the strictest applicable law and then quietly limit that compliance to the postcodes that require it. California residents get an easy cancel button. Everyone else gets the ten-minute retention spiel. It’s not that businesses can’t build the friendly version. They’ve built it already. They just don’t want to give it to you unless a regulator makes them.

That’s the bit that gets me. This isn’t a technical problem. It’s a decision, made in a meeting, by people who get bonused on retention numbers. Someone in that Adobe thread mentioned working somewhere that paid a chatbot vendor a million pounds a year for exactly this kind of “customer experience,” and the person who championed it got a fat bonus for the drop in churn it produced. Churn, in this context, means people who wanted to leave and couldn’t. That’s not a bug tracker issue. That’s the business model working as intended.

I manage infrastructure for a living, so I’ve got a professional soft spot for systems that do what they say they’ll do. There’s something almost admirable, in a bleak way, about how deliberately a cancellation flow can be engineered to fail softly. Enough friction that most people give up, but never quite enough that you can call it fraud outright. My own experience with an ISP a few years back: cancelling took three calls, two “let me transfer you,” and a bloke who genuinely tried to talk me out of moving house. I got there eventually. Not everyone does, and that’s presumably the point.

The Melbourne version of this is less dramatic but just as familiar. Gym memberships that require a written letter, posted, thirty days in advance. Streaming services that let you sign up with one tap and cancel through a maze. I don’t think this is uniquely American corporate culture, it’s just that America has more scale and more lawyers testing the edges of what “technically legal” can stretch to.

Whether a mayor, even one running a city with a GDP the size of Sweden’s, can actually force Netflix’s hand is a genuinely open question. City-level regulation feels like a workaround for the fact that the federal version of this rule existed under Biden’s FTC and got knocked out by a court on procedural grounds before it ever took effect. That’s the bit worth sitting with: a plainly popular, plainly sensible protection got killed not because anyone argued it was a bad idea, but because of process. Whether that’s genuine legal reasoning or a captured system finding a technical excuse to do nothing, I honestly don’t know. Probably both, depending who you ask.

What I do know is that a cancel button shouldn’t be a personality test. If a company can build a seamless one-click signup, it can build a seamless one-click exit, they just don’t want to. Making that the law, in NYC or California or eventually, hopefully, everywhere else, isn’t radical. It’s just closing a door that should never have been open. Good luck getting it to hold.