5 Things We Got Wrong About Stripe Billing

April 2, 2026 | 9 min read Stripe is excellent. Their documentation is among the best in the industry. Their APIs are well-designed and developer-friendly. And yet, across five product launches, we managed to get billing wrong in five different ways. Not because Stripe is hard to use, but because billing is hard to think about correctly when you are focused on building features. We are Obsidian Clad Labs, a small group of friends from Tennessee. We run five SaaS products, each with its own pricing, plans, and billing logic. Here are the five mistakes we made so you can learn from our pain instead of your own. Mistake 1: Not Testing Webhooks Thoroughly Before Going Live Stripe communicates subscription changes to your backend through webhooks -- HTTP POST requests sent to an endpoint on your server whenever something happens: a subscription is created, a payment succeeds, a payment fails, a subscription is canceled. Your backend needs to handle each of these events correctly to keep you