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What's up with webhooks?

Webhooks are used extensively at Stripe and are a great way to make sure your database is up to date with Stripe. They take care, amongst other things, to let you know a trial is over (first charge of their credit card), a subscription is renewed or a charge has failed (after Stripe’s retried)—thus the subscription should be canceled.

To test webhooks locally you can use a service like ngrok.com. Though Stripe also provides a CLI to work with their webhooks (amongst other things).

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