From 0e943019c7771522bef6b08c364580b2ab7c3088 Mon Sep 17 00:00:00 2001
From: Sakariyah Abdulhazeem <sakariyahabdulhazeem@gmail.com>
Date: Thu, 27 Aug 2026 19:07:37 +0100
Subject: [PATCH] feat: persist webhook retry state

---
 .../migration.sql                             |  8 ++++
 prisma/schema.prisma                          | 40 +++++++++++++++++++
 src/services/webhook.ts                       | 13 ++++++
 3 files changed, 61 insertions(+)
 create mode 100644 prisma/migrations/20260827130000_add_webhook_retry_state/migration.sql

diff --git a/prisma/migrations/20260827130000_add_webhook_retry_state/migration.sql b/prisma/migrations/20260827130000_add_webhook_retry_state/migration.sql
new file mode 100644
index 0000000..3b12279
--- /dev/null
+++ b/prisma/migrations/20260827130000_add_webhook_retry_state/migration.sql
@@ -0,0 +1,8 @@
+ALTER TABLE "WebhookDelivery"
+  ADD COLUMN IF NOT EXISTS "attemptCount" INTEGER NOT NULL DEFAULT 0,
+  ADD COLUMN IF NOT EXISTS "nextRetryAt" TIMESTAMP(3),
+  ADD COLUMN IF NOT EXISTS "status" TEXT NOT NULL DEFAULT 'pending',
+  ADD COLUMN IF NOT EXISTS "lastError" TEXT;
+
+CREATE INDEX IF NOT EXISTS "WebhookDelivery_status_nextRetryAt_idx"
+  ON "WebhookDelivery"("status", "nextRetryAt");
diff --git a/prisma/schema.prisma b/prisma/schema.prisma
index a68eeba..ad8f01c 100644
--- a/prisma/schema.prisma
+++ b/prisma/schema.prisma
@@ -28,6 +28,7 @@ model User {
   approvals        TreasuryApproval[]
   auditLogs        AuditLog[]
   idempotencyKeys  IdempotencyKey[]
+  webhooks         Webhook[]
 
   @@map("users")
 }
@@ -52,6 +53,7 @@ model Group {
   invites     Invite[]
   invitations Invitation[]
   auditLogs   AuditLog[]
+  webhooks    Webhook[]
 
   @@index([createdByUserId])
   @@map("groups")
@@ -73,6 +75,44 @@ model GroupMember {
   @@map("group_members")
 }
 
+model Webhook {
+  id        String   @id @default(cuid())
+  groupId   String?  @map("groupId")
+  userId    String?  @map("userId")
+  url       String
+  secret    String
+  events    String[]
+  enabled   Boolean  @default(true)
+  createdAt DateTime @default(now())
+  updatedAt DateTime @updatedAt
+  deliveries WebhookDelivery[]
+  group Group? @relation(fields: [groupId], references: [id], onDelete: Cascade)
+  user User? @relation(fields: [userId], references: [id], onDelete: Cascade)
+  @@index([groupId])
+  @@index([userId])
+  @@map("Webhook")
+}
+
+model WebhookDelivery {
+  id                 String   @id @default(cuid())
+  webhookId          String
+  eventType          String
+  payload            Json
+  responseStatusCode Int?
+  responseBody       String?
+  success            Boolean  @default(false)
+  attempts           Int      @default(0)
+  attemptCount       Int      @default(0)
+  nextRetryAt        DateTime?
+  status             String   @default("pending")
+  lastError          String?
+  createdAt          DateTime @default(now())
+  webhook Webhook @relation(fields: [webhookId], references: [id], onDelete: Cascade)
+  @@index([webhookId, createdAt])
+  @@index([status, nextRetryAt])
+  @@map("WebhookDelivery")
+}
+
 model Expense {
   id          String   @id @default(cuid())
   groupId     String   @map("group_id")
diff --git a/src/services/webhook.ts b/src/services/webhook.ts
index f0924c8..bd16d79 100644
--- a/src/services/webhook.ts
+++ b/src/services/webhook.ts
@@ -50,6 +50,10 @@ async function deliver(
       responseBody: null,
       success: false,
       attempts: 0,
+      attemptCount: 0,
+      nextRetryAt: new Date(),
+      status: "pending",
+      lastError: null,
     },
   });
 
@@ -89,6 +93,10 @@ async function deliver(
             responseBody: lastResponseBody,
             success: true,
             attempts: attempt,
+            attemptCount: attempt,
+            nextRetryAt: null,
+            status: "delivered",
+            lastError: null,
           },
         });
         return;
@@ -101,6 +109,7 @@ async function deliver(
       clearTimeout(timeout);
     }
 
+    const exhausted = attempt === MAX_ATTEMPTS;
     await (prisma as any).webhookDelivery.update({
       where: { id: delivery.id },
       data: {
@@ -108,6 +117,10 @@ async function deliver(
         responseBody: lastResponseBody,
         success: false,
         attempts: attempt,
+        attemptCount: attempt,
+        nextRetryAt: exhausted ? null : new Date(Date.now() + RETRY_DELAYS_MS[attempt - 1]),
+        status: exhausted ? "failed" : "pending",
+        lastError: lastResponseBody,
       },
     });
   }