From d2b7aa6897983c6cd3bf9b44e5a5931c97a1126e Mon Sep 17 00:00:00 2001
From: Moheeb Zara <hackbuildvideo@gmail.com>
Date: Mon, 18 May 2026 18:34:03 -0700
Subject: [PATCH] fix(stripe): never rewind billing period on out-of-order
 webhooks (D5)

Stripe doesn't guarantee event order. A late customer.subscription.
updated carrying an older period overwrote a newer current_period_end,
so graceExceeded flipped a paid member to 'late' and fired a false
'dues lapsed' email + access loss. applySubscription now reads the
stored period and keeps the later of stored vs incoming
(laterPeriodEnd, pure + tested); status still tracks latest sub.status
but grace is computed from the monotonic period.
---
 __tests__/stripe-webhook-logic.test.ts  | 17 +++++++++++++++++
 app/api/stripe/webhook/[space]/route.ts | 18 +++++++++++++++++-
 lib/stripe/webhook-logic.ts             | 15 +++++++++++++++
 3 files changed, 49 insertions(+), 1 deletion(-)

diff --git a/__tests__/stripe-webhook-logic.test.ts b/__tests__/stripe-webhook-logic.test.ts
index 6cb5259..663be73 100644
--- a/__tests__/stripe-webhook-logic.test.ts
+++ b/__tests__/stripe-webhook-logic.test.ts
@@ -8,6 +8,7 @@ import {
   memberStatusPatch,
   stripeInvoiceToPaymentRow,
   minorToMajor,
+  laterPeriodEnd,
 } from '@/lib/stripe/webhook-logic'
 
 describe('isoFromUnix', () => {
@@ -123,6 +124,22 @@ describe('stripeInvoiceToPaymentRow', () => {
   })
 })
 
+describe('laterPeriodEnd (never rewind on out-of-order events)', () => {
+  const older = '2026-05-01T00:00:00.000Z'
+  const newer = '2026-06-01T00:00:00.000Z'
+  it('keeps the later of stored vs incoming regardless of arrival order', () => {
+    expect(laterPeriodEnd(newer, older)).toBe(newer) // stale event arrives late
+    expect(laterPeriodEnd(older, newer)).toBe(newer) // normal advance
+    expect(laterPeriodEnd(newer, newer)).toBe(newer)
+  })
+  it('handles nulls (first event / canceled sub with no period)', () => {
+    expect(laterPeriodEnd(null, newer)).toBe(newer)
+    expect(laterPeriodEnd(newer, null)).toBe(newer)
+    expect(laterPeriodEnd(null, null)).toBeNull()
+    expect(laterPeriodEnd(undefined, undefined)).toBeNull()
+  })
+})
+
 describe('minorToMajor', () => {
   it('divides by 100, treats nullish as 0', () => {
     expect(minorToMajor(2500)).toBe(25)
diff --git a/app/api/stripe/webhook/[space]/route.ts b/app/api/stripe/webhook/[space]/route.ts
index d257fe4..a5239ac 100644
--- a/app/api/stripe/webhook/[space]/route.ts
+++ b/app/api/stripe/webhook/[space]/route.ts
@@ -21,6 +21,7 @@ import {
   memberStatusPatch,
   stripeInvoiceToPaymentRow,
   minorToMajor,
+  laterPeriodEnd,
 } from '@/lib/stripe/webhook-logic'
 import {
   renderDuesEmail,
@@ -193,7 +194,22 @@ export async function POST(
       customerId,
     )
     if (!memberId) return
-    const periodEnd = subscriptionPeriodEnd(sub)
+    const incomingPeriodEnd = subscriptionPeriodEnd(sub)
+
+    // Never rewind the period on a stale/out-of-order event. Status still
+    // reflects the latest sub.status, but graceExceeded is computed from the
+    // monotonic (non-rewound) period so a late event can't false-lapse a
+    // paid member.
+    const { data: existingBilling } = await admin
+      .from('member_billing')
+      .select('current_period_end')
+      .eq('space_id', spaceId)
+      .eq('member_id', memberId)
+      .maybeSingle()
+    const periodEnd = laterPeriodEnd(
+      (existingBilling?.current_period_end as string | null) ?? null,
+      incomingPeriodEnd,
+    )
 
     await admin.from('member_billing').upsert(
       {
diff --git a/lib/stripe/webhook-logic.ts b/lib/stripe/webhook-logic.ts
index 7457fed..d103091 100644
--- a/lib/stripe/webhook-logic.ts
+++ b/lib/stripe/webhook-logic.ts
@@ -99,3 +99,18 @@ export function stripeInvoiceToPaymentRow(args: {
 export function minorToMajor(amount: number | null | undefined): number {
   return (amount ?? 0) / 100
 }
+
+// Stripe does not guarantee webhook ordering. A stale/late
+// customer.subscription.updated carrying an OLDER period must never rewind
+// the stored current_period_end (that would make graceExceeded flip a paid
+// member to 'late' and fire a false "dues lapsed" email). Keep the later of
+// stored vs incoming. ISO-8601 UTC ('...Z') strings sort lexically ==
+// chronologically, so string compare is correct here.
+export function laterPeriodEnd(
+  stored: string | null | undefined,
+  incoming: string | null | undefined,
+): string | null {
+  if (!stored) return incoming ?? null
+  if (!incoming) return stored
+  return stored >= incoming ? stored : incoming
+}