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fix: preserve active Pro entitlement on stale Stripe webhooks #2336

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fix: preserve active Pro entitlement on stale Stripe webhooks #2336

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85fdf8c
fix: preserve active Pro entitlement on stale Stripe webhooks
richiemcilroy Sep 22, 2026
cf29d33
fix: check all Stripe subscription pages for Pro entitlement
richiemcilroy Sep 22, 2026
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98 changes: 98 additions & 0 deletions apps/web/__tests__/unit/signed-baa-webhook.test.ts
View file
Open in desktop
Original file line number Diff line number Diff line change
Expand Up @@ -1062,4 +1062,102 @@ describe("Signed BAA Payment Link webhooks", () => {
);
expect(mockDbChain.update).not.toHaveBeenCalledWith(signedBaas);
});

it.each(["customer.subscription.updated", "customer.subscription.deleted"])(
"keeps a newer active Pro subscription when an old checkout receives %s",
async (eventType) => {
const oldSubscription = {
...proSubscription,
id: "sub_old",
status: eventType.endsWith("deleted")
? "canceled"
: "incomplete_expired",
};
const activeSubscription = {
...proSubscription,
id: "sub_active",
items: { data: [{ price: { id: "price_pro" }, quantity: 3 }] },
};
const pastDueSubscription = {
...proSubscription,
id: "sub_past_due",
status: "past_due",
items: { data: [{ price: { id: "price_pro" }, quantity: 2 }] },
};
mockStripe.webhooks.constructEvent.mockReturnValue({
type: eventType,
data: { object: oldSubscription },
});
mockStripe.customers.retrieve.mockResolvedValue({
id: "cus_pro",
email: owner.email,
metadata: { userId: owner.id },
});
mockStripe.subscriptions.list.mockResolvedValue({
data: [oldSubscription, pastDueSubscription, activeSubscription],
});
if (eventType.endsWith("deleted")) {
mockDbChain.where.mockResolvedValueOnce([owner]);
} else {
mockDbChain.limit.mockResolvedValueOnce([owner]);
}

expect((await POST(makeWebhookRequest())).status).toBe(200);
expect(mockDbChain.set).toHaveBeenCalledWith(
expect.objectContaining({
stripeSubscriptionId: "sub_active",
stripeSubscriptionStatus: "active",
inviteQuota: 5,
}),
);
},
);

it.each(["customer.subscription.updated", "customer.subscription.deleted"])(
"finds Pro entitlement on a later Stripe page for %s",
async (eventType) => {
const oldSubscription = {
...proSubscription,
id: "sub_old",
status: eventType.endsWith("deleted")
? "canceled"
: "incomplete_expired",
};
const activeSubscription = {
...proSubscription,
id: "sub_active",
items: { data: [{ price: { id: "price_pro" }, quantity: 2 }] },
};
mockStripe.webhooks.constructEvent.mockReturnValue({
type: eventType,
data: { object: oldSubscription },
});
mockStripe.customers.retrieve.mockResolvedValue({
id: "cus_pro",
email: owner.email,
metadata: { userId: owner.id },
});
mockStripe.subscriptions.list
.mockReset()
.mockResolvedValueOnce({ data: [oldSubscription], has_more: true })
.mockResolvedValueOnce({ data: [activeSubscription], has_more: false });
if (eventType.endsWith("deleted")) {
mockDbChain.where.mockResolvedValueOnce([owner]);
} else {
mockDbChain.limit.mockResolvedValueOnce([owner]);
}

expect((await POST(makeWebhookRequest())).status).toBe(200);
expect(mockStripe.subscriptions.list).toHaveBeenCalledWith(
expect.objectContaining({ starting_after: "sub_old" }),
);
expect(mockDbChain.set).toHaveBeenCalledWith(
expect.objectContaining({
stripeSubscriptionId: "sub_active",
stripeSubscriptionStatus: "active",
inviteQuota: 2,
}),
);
},
);
});
122 changes: 84 additions & 38 deletions apps/web/app/api/webhooks/stripe/route.ts
View file
Open in desktop
Original file line number Diff line number Diff line change
Expand Up @@ -124,6 +124,63 @@ function hasEntitledProSubscription(subscriptions: Stripe.Subscription[]) {
);
}

function effectiveProSubscription(
eventSubscription: Stripe.Subscription,
subscriptions: Stripe.Subscription[],
) {
const current =
subscriptions.find((sub) => sub.id === eventSubscription.id) ??
eventSubscription;
return (
subscriptions.find(
(sub) =>
isProSubscription(sub) &&
(sub.status === "active" || sub.status === "trialing"),
) ??
subscriptions.find(
(sub) => isProSubscription(sub) && sub.status === "past_due",
) ??
current
);
}

function proInviteQuota(subscriptions: Stripe.Subscription[]) {
return subscriptions
.filter(
(sub) =>
isProSubscription(sub) &&
ENTITLED_SUBSCRIPTION_STATUSES.has(sub.status),
)
.reduce(
(total, sub) =>
total +
sub.items.data.reduce(
(subTotal, item) => subTotal + (item.quantity || 1),
0,
),
0,
);
}

async function listCustomerSubscriptions(customerId: string) {
const subscriptions: Stripe.Subscription[] = [];
let startingAfter: string | undefined;
while (true) {
const page = await stripe().subscriptions.list({
customer: customerId,
status: "all",
limit: 100,
...(startingAfter ? { starting_after: startingAfter } : {}),
});
subscriptions.push(...page.data);
if (!page.has_more) return subscriptions;
const last = page.data.at(-1);
if (!last)
throw new Error("Stripe subscription pagination did not advance");
startingAfter = last.id;
}
}

async function cancelEntitledBaaSubscriptions(
subscriptions: Stripe.Subscription[],
customerId: string,
Expand Down Expand Up @@ -702,21 +759,17 @@ export const POST = async (req: Request) => {
foundUserId,
);

const subscriptions = await stripe().subscriptions.list({
customer: customer.id,
status: "all",
limit: 100,
});
const subscriptions = await listCustomerSubscriptions(customer.id);

console.log("Retrieved all subscriptions:", {
count: subscriptions.data.length,
count: subscriptions.length,
});

// BAA cleanup depends only on Stripe state, so it must run even
// when the customer cannot be mapped to a user; the 202 below is
// treated as delivered and the event is never redelivered.
if (!hasEntitledProSubscription(subscriptions.data)) {
await cancelEntitledBaaSubscriptions(subscriptions.data, customer.id);
if (!hasEntitledProSubscription(subscriptions)) {
await cancelEntitledBaaSubscriptions(subscriptions, customer.id);
}

if (!dbUser) {
Expand All @@ -737,34 +790,24 @@ export const POST = async (req: Request) => {
// Quota follows entitlement: past_due keeps its seats during the
// dunning window instead of collapsing the org to zero while
// Stripe retries the card.
const inviteQuota = subscriptions.data
.filter(
(sub) =>
ENTITLED_SUBSCRIPTION_STATUSES.has(sub.status) &&
isProSubscription(sub),
)
.reduce((total, sub) => {
return (
total +
sub.items.data.reduce(
(subTotal, item) => subTotal + (item.quantity || 1),
0,
)
);
}, 0);
const currentSubscription = effectiveProSubscription(
subscription,
subscriptions,
);
const inviteQuota = proInviteQuota(subscriptions);

console.log("Updating user in database with:", {
subscriptionId: subscription.id,
status: subscription.status,
subscriptionId: currentSubscription.id,
status: currentSubscription.status,
customerId: customer.id,
inviteQuota,
});

await db()
.update(users)
.set({
stripeSubscriptionId: subscription.id,
stripeSubscriptionStatus: subscription.status,
stripeSubscriptionId: currentSubscription.id,
stripeSubscriptionStatus: currentSubscription.status,
stripeCustomerId: customer.id,
inviteQuota: inviteQuota,
})
Expand Down Expand Up @@ -880,17 +923,20 @@ export const POST = async (req: Request) => {
// BAA cleanup depends only on Stripe state; it must run before the
// user-mapping early returns so an unmappable customer can't keep
// an active BAA billing after their last Pro subscription ends.
const remainingSubscriptions = await stripe().subscriptions.list({
customer: customer.id,
status: "all",
limit: 100,
});
if (!hasEntitledProSubscription(remainingSubscriptions.data)) {
const remainingSubscriptions = await listCustomerSubscriptions(
customer.id,
);
if (!hasEntitledProSubscription(remainingSubscriptions)) {
await cancelEntitledBaaSubscriptions(
remainingSubscriptions.data,
remainingSubscriptions,
customer.id,
);
}
const currentSubscription = effectiveProSubscription(
subscription,
remainingSubscriptions,
);
const inviteQuota = proInviteQuota(remainingSubscriptions) || 1;

let foundUserId: User.UserId | undefined;
if ("metadata" in customer) {
Expand Down Expand Up @@ -940,16 +986,16 @@ export const POST = async (req: Request) => {
await db()
.update(users)
.set({
stripeSubscriptionId: subscription.id,
stripeSubscriptionStatus: subscription.status,
inviteQuota: 1,
stripeSubscriptionId: currentSubscription.id,
stripeSubscriptionStatus: currentSubscription.status,
inviteQuota,
})
.where(eq(users.id, foundUserId));
await enqueueLoopsSync(db(), foundUserId);

console.log("User updated successfully", {
foundUserId,
inviteQuota: 1,
inviteQuota,
});
}

Expand Down
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