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I’m not sure why the webhooks weren’t working. Perhaps you changed API keys after webhooks were created? Or changed signing secrets in the settings. It would show error in the log though if you did. We never had such situation in the past. Few other issues related to webhooks that our customers had were caused either by their server config that was blocking webhooks from Stripe or by improper manually configured webhooks (when those were created via Stripe Dashboard by the customer instead of using “Create Webhook” buttons on add-on settings page).
Create a plan in test mode in the plugin, but make it “daily for 3 days” instead of monthly. Then create a product with this test plan and make a test purchase using one of these test cards: https://stripe.com/docs/testing#cards. It should automatically “end” itself in 3 days, you can see that by watching the subscription on Subscriptions page of the plugin.
If test mode webhooks are working, then, most likely, Live webhooks would be working as well. When you have a first live purchase, just find the subscription on Subscriptions page of the plugin and see if events are properly populated (e.g. “regular payment made” should be right after “subscription created” event). Just look how it goes with your daily test plan, same events should be there for your live plan (except that it would happen monthly, not daily).