Stripe Chargeback Protection

Keep in mind that making it easy to terminate subscriptions eliminates most of those chargebacks.

It’s one of the reasons that I use Apple whenever possible to handle recurring subscriptions. It takes about 10m to file a dispute with American Express. If figuring out how to cancel a subscription takes longer, I’m cutting my losses at 10m and heading to Amex.com.

Perhaps industry standards around subscription management would help? I think there is a lot of real fraud/unethical behavior exists in this space and legitimate retention management can easily cross the line in the consumers mind as scammy.

There is no legitimate retention management. If I want to cancel I've made clear what I want to do. Making it take longer then a few minutes is a waste of all our time.

One of the reasons I left my first job out of college is that management wanted the cancel subscription button on our website replaced with a phone number.

The other side of this is that there are some customers who can't manage to cancel a subscription even when they literally just have to log in, click/tap to go to whatever page handles their personal details, and then push a prominent button to cancel and maybe a second confirmation one to prevent misclicks. The entire process can take less than 10s, yet you'll still get people who email you claiming they can't find it and have been looking forever and now they'd like a refund for their last six months of payments please. Remarkably, although they have trying to cancel for months and have looked everywhere, some of these people have no entry in your logs showing them visiting any of the personal settings pages on your system, nor is there any record of any previous attempt to contact you via any of the five different methods you advertise prominently for customer support...

Now, we're generally fairly relaxed about subscriptions. We very much take the view that it's not worth quibbling over the odd month's payment and we'd rather offer good customer service and build a good reputation. For example, maybe someone seems to have made an honest mistake but we believe they really did intend to cancel and they haven't used our services since, and in that sort of situation we tend to just refund them anyway if they ask.

However, cancelling a payment authority or charging a payment back retrospectively is not a substitute for cancelling a legal agreement, and in some cases it also hurts us. If someone deliberately messes us around like that, we are much less sympathetic, and we certainly consider whether to pursue them through legal means to recover what they owed us and any other damages and costs.

There is a fine line in my POV.

Word trickery and playing games with buttons is over the line.

I think it is ok to say “Hey, you’re paying $20/mo for the super plan, and don’t use feature X, but can do the middle plan for $12”. I think it’s ok to make sure that people understand that data is deleted if they take the action. But it’s easy to drift into dark patterns.

I think this is fair, but do you ever manage to actually recover the funds?

I'll answer your question, but I should say up-front that my businesses mostly deal with relatively low-value transactions, so although action is always considered in these cases, usually we decide it's not worth pursuing. On the occasions that it's been deemed worthwhile and we have started the recovery process, we have never reached the stage of formal court proceedings. Generally once someone realises that their actions were not acceptable and we really are willing to go further if necessary, that tends to resolve things quickly. So I suppose the honest answer is yes, we did get our money and sometimes a bit more than the original amount owed due to interest/penalties/etc, but I don't know how effective our intended next steps would really have been other than where we've had positive legal advice.