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Hi, let me help you with this.
Stripe Checkout is not designed for automated testing. The problem might be in captcha.
I have never faced a captch, is it something that can happen?
Yes, it's present on all Stripe surfaces to battle card testing and other fraud, but sometimes it's not visible.
I would recommend just mocking Stripe payments for your automated tests.
How should I mock it?
I want to simulate the process of a customer making a payment via checkout session and all of its events (webhooks)
Honestly that wouldn't be easy. You would either need to mock all webhook events yourself. Or have a way to let your app know you're testing and simplify the payloads.