I started using Cursor somewhere in early 2025, around February or March. Before that, I had been copy-pasting from ChatGPT into JetBrains Rider. Then Rider released its own AI assistant, and I used that for a couple of months. When I switched to Cursor, the productivity shift was noticeable enough that I signed up for the paid subscription pretty quickly after trying the free version.
For most of the year, Cursor was my primary tool. Around November, through Improving, I got access to Windsurf and started splitting time between the two. The transition was smooth because the tools are similar in how they work. Cursor had things Windsurf didn’t at the time: a plan mode, an auto mode for model selection (which I used by default, bumping up to a specific model only when needed), and a debug mode. Windsurf has since added a plan mode and an adaptive model selection option (though it isn’t available on my business license yet). The debug mode is still missing. But Windsurf has been handling things well enough that neither gap has been a real blocker.
Over the last four months or so, I’ve moved most of my work to Windsurf. That’s what led me to evaluate whether I still needed the Cursor license.
What I Found When I Went to Cancel
On April 8th, I visited my Cursor profile to cancel the subscription. The page showed: Your subscription will auto-renew on April 12th. Four days from now, I thought. I can cancel before then.
When I clicked into the cancellation flow, that’s when I found out the truth: the subscription had already renewed. In March. I just hadn’t known.
Three things had failed at once:
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No email reminder before the renewal
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No email confirmation after the renewal
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The dashboard showing an incorrect renewal date (April 12, when it had already been processed in March)
The only way I learned the charge had happened was by clicking into the payment section, which redirected me to Stripe. Nothing on the main Cursor profile had indicated the renewal was already done.
Because I’m on an annual plan, that’s twelve months paid up front.
The Support Conversation
I emailed support with screenshots and a straightforward ask: cancel the annual renewal and charge me for the one month I had used since it renewed. I wasn’t asking for everything back. I was asking for something proportional given the circumstances.
The first response came fast, clearly from an AI agent. It misread my request as wanting a refund for previous months and declined.
I clarified. The AI declined again, citing refund eligibility requirements.
I asked to speak with a human.
About thirty minutes later, a billing associate responded. They acknowledged the frustration, then cited the terms of service: annual subscriptions are non-refundable once the billing period starts. They also noted that a one-time courtesy refund exists for accidental renewals, but only when there has been no usage. My account showed usage after the renewal date.
That was it. No exceptions to policy. Subscription canceled, access running through March 2027.
What I Said Before I Left
I told them I was removing Cursor from the list of tools I recommend and that I’d explain why publicly. This is that explanation.
I want to be clear about what I was asking: not a free pass. I had been using the tool since the renewal. I asked them to acknowledge the circumstances—no reminder, an incorrect dashboard, and no post-renewal confirmation—and to find a reasonable solution. “Charge me one month at the monthly rate, cancel the annual” is a specific and modest ask.
The billing associate did acknowledge one thing: the dashboard renewal date was a known bug and was being fixed.
What This Is Actually About
I spend a lot of time helping businesses think through what they’re building and for whom. A question I come back to often: what’s the customer value here, not just the business value?
Annual subscriptions make sense for businesses. Predictable revenue, lower churn, discounted rate for the customer in exchange for a commitment. Those are real benefits on both sides. But that commitment goes two ways. When a customer locks in for a year, they’re trusting you with both their money and their time. That creates a relational obligation that includes basic transparency: a heads-up before renewal, confirmation afterward, and accurate information in your UI.
Those aren’t extras. They’re the minimum for a trust-based relationship.
When a customer reaches out because those basics weren’t there, how you respond either repairs the relationship or ends it. A series of AI-deflected responses, followed by policy citations, says something about where the priorities lie. I’m not saying the people involved were unkind – they weren’t. But the system wasn’t designed to take cases where the customer has a legitimate point seriously.
I recommended Cursor to a lot of people over the past year. That recommendation came from real experience with the tool. It’s genuinely good at what it does. But a tool’s quality and a business’s practices are separate things. Both show up in my decision about whether I’ll put my name behind a recommendation going forward.
If I’m helping a business figure out what to build and why, this is exactly the kind of story I’d use to ground the conversation. It’s easy to point at a policy and say it protects the business. It’s harder to notice when that same policy is quietly eroding the relationships that made the business worth protecting in the first place.
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