From ca9a70ced580c5a73c9b1c0e2672c256ad000858 Mon Sep 17 00:00:00 2001
From: Lucas Smith <me@lucasjamessmith.me>
Date: Mon, 14 Jul 2025 12:31:06 +1000
Subject: [PATCH] fix: handle trials and resubscribing (#1897)

---
 .../early-adopter-checkout-metadata.ts        | 13 --------
 .../stripe/webhook/on-subscription-created.ts | 32 +++++++++++++++----
 .../stripe/webhook/on-subscription-updated.ts |  8 ++++-
 3 files changed, 33 insertions(+), 20 deletions(-)
 delete mode 100644 packages/ee/server-only/stripe/webhook/early-adopter-checkout-metadata.ts

diff --git a/packages/ee/server-only/stripe/webhook/early-adopter-checkout-metadata.ts b/packages/ee/server-only/stripe/webhook/early-adopter-checkout-metadata.ts
deleted file mode 100644
index 7d8c65a09..000000000
--- a/packages/ee/server-only/stripe/webhook/early-adopter-checkout-metadata.ts
+++ /dev/null
@@ -1,13 +0,0 @@
-import { z } from 'zod';
-
-export const ZEarlyAdopterCheckoutMetadataSchema = z.object({
-  name: z.string(),
-  email: z.string(),
-  signatureText: z.string(),
-  signatureDataUrl: z.string().optional(),
-  source: z.literal('marketing'),
-});
-
-export type TEarlyAdopterCheckoutMetadataSchema = z.infer<
-  typeof ZEarlyAdopterCheckoutMetadataSchema
->;
diff --git a/packages/ee/server-only/stripe/webhook/on-subscription-created.ts b/packages/ee/server-only/stripe/webhook/on-subscription-created.ts
index 21e659518..bf1f10f3c 100644
--- a/packages/ee/server-only/stripe/webhook/on-subscription-created.ts
+++ b/packages/ee/server-only/stripe/webhook/on-subscription-created.ts
@@ -81,17 +81,34 @@ export const onSubscriptionCreated = async ({ subscription }: OnSubscriptionCrea
 
   const status = match(subscription.status)
     .with('active', () => SubscriptionStatus.ACTIVE)
+    .with('trialing', () => SubscriptionStatus.ACTIVE)
     .with('past_due', () => SubscriptionStatus.PAST_DUE)
     .otherwise(() => SubscriptionStatus.INACTIVE);
 
-  await prisma.subscription.create({
-    data: {
+  const periodEnd =
+    subscription.status === 'trialing' && subscription.trial_end
+      ? new Date(subscription.trial_end * 1000)
+      : new Date(subscription.current_period_end * 1000);
+
+  await prisma.subscription.upsert({
+    where: {
+      organisationId,
+    },
+    create: {
       organisationId,
       status,
       customerId,
       planId: subscription.id,
       priceId: subscription.items.data[0].price.id,
-      periodEnd: new Date(subscription.current_period_end * 1000),
+      periodEnd,
+      cancelAtPeriodEnd: subscription.cancel_at_period_end,
+    },
+    update: {
+      status,
+      customerId,
+      planId: subscription.id,
+      priceId: subscription.items.data[0].price.id,
+      periodEnd,
       cancelAtPeriodEnd: subscription.cancel_at_period_end,
     },
   });
@@ -172,14 +189,17 @@ const handleOrganisationUpdate = async ({ customerId, claim }: HandleOrganisatio
   }
 
   // Todo: logging
-  if (organisation.subscription) {
-    console.error('Organisation already has a subscription');
+  if (
+    organisation.subscription &&
+    organisation.subscription.status !== SubscriptionStatus.INACTIVE
+  ) {
+    console.error('Organisation already has an active subscription');
 
     // This should never happen
     throw Response.json(
       {
         success: false,
-        message: `Organisation already has a subscription`,
+        message: `Organisation already has an active subscription`,
       } satisfies StripeWebhookResponse,
       { status: 500 },
     );
diff --git a/packages/ee/server-only/stripe/webhook/on-subscription-updated.ts b/packages/ee/server-only/stripe/webhook/on-subscription-updated.ts
index 601adca51..128fe3a8d 100644
--- a/packages/ee/server-only/stripe/webhook/on-subscription-updated.ts
+++ b/packages/ee/server-only/stripe/webhook/on-subscription-updated.ts
@@ -83,9 +83,15 @@ export const onSubscriptionUpdated = async ({
 
   const status = match(subscription.status)
     .with('active', () => SubscriptionStatus.ACTIVE)
+    .with('trialing', () => SubscriptionStatus.ACTIVE)
     .with('past_due', () => SubscriptionStatus.PAST_DUE)
     .otherwise(() => SubscriptionStatus.INACTIVE);
 
+  const periodEnd =
+    subscription.status === 'trialing' && subscription.trial_end
+      ? new Date(subscription.trial_end * 1000)
+      : new Date(subscription.current_period_end * 1000);
+
   await prisma.$transaction(async (tx) => {
     await tx.subscription.update({
       where: {
@@ -96,7 +102,7 @@ export const onSubscriptionUpdated = async ({
         status: status,
         planId: subscription.id,
         priceId: subscription.items.data[0].price.id,
-        periodEnd: new Date(subscription.current_period_end * 1000),
+        periodEnd,
         cancelAtPeriodEnd: subscription.cancel_at_period_end,
       },
     });