Keep Pro through failed-payment retries + dunning emails - #2074
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…etry window A past_due subscription previously lost Pro on the first failed charge and the billing card fell back to the Upgrade to Pro state as if no subscription existed. past_due now retains entitlement until Stripe exhausts retries and moves the sub to canceled/unpaid, and the billing card shows an explicit payment-failed state pointing at the payment method fix.
Handle invoice.payment_failed for renewals and plan changes: email on the first failure and the final retry (idempotent via Resend idempotency keys), linking to billing settings. Also compute inviteQuota from all entitled subscription statuses (active, trialing, past_due) so an org's seats no longer collapse to zero while Stripe retries the card. Note: the Stripe webhook endpoint must have invoice.payment_failed added to its enabled events after this deploys; it currently only sends checkout and subscription events.
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Why
Failed payments currently get the harshest possible treatment, which makes them a meaningful and avoidable source of churn:
userIsPro()excludedpast_due, so access dropped on the first failed charge with no grace window.invoice.payment_failedwas not in the webhook's relevant events (the handler 400s it), and no billing email of any kind existed.What
past_dueretains Pro entitlement (userIsPro,isAiGenerationEnabledForUser) until Stripe exhausts retries and moves the sub tocanceled/unpaid, which is when access actually drops. The grace window is therefore bounded by the Stripe retry schedule, no timer of our own.getSubscriptionDetailspasses past_due through.payment-failedemail template (matches existing email styling); webhook handlesinvoice.payment_failedforsubscription_cycle/subscription_updateinvoices, emailing on the first failure and the final retry only. Idempotent via Resend idempotency keys, so Stripe webhook retries can't double-send.Activation (after deploy)
The production Stripe webhook endpoint must have
invoice.payment_failedadded to its enabled events once this is live, otherwise the dunning path never fires. Deliberately not done yet so events don't hit an endpoint that 400s them.Testing
pro-entitlement-grace.test.ts), full apps/web unit suite run: 1290 passed, 1 pre-existing unrelated failure (slack-app-manifest.test.tscolor constant, also failing on main).tscclean on apps/web and packages/utils.Immediate effect on merge
Existing past_due subscriptions regain Pro access and see the fix-your-card state instead of the upgrade pitch.