diff --git a/packages/twenty-server/src/database/typeorm/core/migrations/billing/1739981257356-addOnUpdateInEntitlements.ts b/packages/twenty-server/src/database/typeorm/core/migrations/billing/1739981257356-addOnUpdateInEntitlements.ts
new file mode 100644
index 000000000..b8bd5756d
--- /dev/null
+++ b/packages/twenty-server/src/database/typeorm/core/migrations/billing/1739981257356-addOnUpdateInEntitlements.ts
@@ -0,0 +1,25 @@
+import { MigrationInterface, QueryRunner } from 'typeorm';
+
+export class AddOnUpdateInEntitlements1739981257356
+  implements MigrationInterface
+{
+  name = 'AddOnUpdateInEntitlements1739981257356';
+
+  public async up(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "core"."billingEntitlement" DROP CONSTRAINT "FK_766a1918aa3dbe0d67d3df62356"`,
+    );
+    await queryRunner.query(
+      `ALTER TABLE "core"."billingEntitlement" ADD CONSTRAINT "FK_766a1918aa3dbe0d67d3df62356" FOREIGN KEY ("stripeCustomerId") REFERENCES "core"."billingCustomer"("stripeCustomerId") ON DELETE CASCADE ON UPDATE CASCADE`,
+    );
+  }
+
+  public async down(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "core"."billingEntitlement" DROP CONSTRAINT "FK_766a1918aa3dbe0d67d3df62356"`,
+    );
+    await queryRunner.query(
+      `ALTER TABLE "core"."billingEntitlement" ADD CONSTRAINT "FK_766a1918aa3dbe0d67d3df62356" FOREIGN KEY ("stripeCustomerId") REFERENCES "core"."billingCustomer"("stripeCustomerId") ON DELETE CASCADE ON UPDATE NO ACTION`,
+    );
+  }
+}
diff --git a/packages/twenty-server/src/engine/core-modules/billing/billing.controller.ts b/packages/twenty-server/src/engine/core-modules/billing/billing.controller.ts
index c579fcb86..3b7f35d0f 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/billing.controller.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/billing.controller.ts
@@ -47,23 +47,34 @@ export class BillingController {
     @Res() res: Response,
   ) {
     if (!req.rawBody) {
-      res.status(400).end();
-
-      return;
+      throw new BillingException(
+        'Missing request body',
+        BillingExceptionCode.BILLING_MISSING_REQUEST_BODY,
+      );
     }
-    const event = this.stripeWebhookService.constructEventFromPayload(
-      signature,
-      req.rawBody,
-    );
 
     try {
+      const event = this.stripeWebhookService.constructEventFromPayload(
+        signature,
+        req.rawBody,
+      );
       const result = await this.handleStripeEvent(event);
 
       res.status(200).send(result).end();
     } catch (error) {
-      if (error instanceof BillingException) {
-        res.status(404).end();
+      if (
+        error instanceof BillingException ||
+        error instanceof Stripe.errors.StripeError
+      ) {
+        throw error;
       }
+      const errorMessage =
+        error instanceof Error ? error.message : JSON.stringify(error);
+
+      throw new BillingException(
+        errorMessage,
+        BillingExceptionCode.BILLING_UNHANDLED_ERROR,
+      );
     }
   }
 
diff --git a/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts b/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
index fceca015c..35b26ea27 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/billing.exception.ts
@@ -16,4 +16,7 @@ export enum BillingExceptionCode {
   BILLING_SUBSCRIPTION_EVENT_WORKSPACE_NOT_FOUND = 'BILLING_SUBSCRIPTION_EVENT_WORKSPACE_NOT_FOUND',
   BILLING_ACTIVE_SUBSCRIPTION_NOT_FOUND = 'BILLING_ACTIVE_SUBSCRIPTION_NOT_FOUND',
   BILLING_METER_EVENT_FAILED = 'BILLING_METER_EVENT_FAILED',
+  BILLING_MISSING_REQUEST_BODY = 'BILLING_MISSING_REQUEST_BODY',
+  BILLING_UNHANDLED_ERROR = 'BILLING_UNHANDLED_ERROR',
+  BILLING_STRIPE_ERROR = 'BILLING_STRIPE_ERROR',
 }
diff --git a/packages/twenty-server/src/engine/core-modules/billing/entities/billing-entitlement.entity.ts b/packages/twenty-server/src/engine/core-modules/billing/entities/billing-entitlement.entity.ts
index f89153cc7..b093064b8 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/entities/billing-entitlement.entity.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/entities/billing-entitlement.entity.ts
@@ -54,6 +54,7 @@ export class BillingEntitlement {
     (billingCustomer) => billingCustomer.billingEntitlements,
     {
       onDelete: 'CASCADE',
+      onUpdate: 'CASCADE',
     },
   )
   @JoinColumn({
diff --git a/packages/twenty-server/src/engine/core-modules/billing/filters/billing-api-exception.filter.ts b/packages/twenty-server/src/engine/core-modules/billing/filters/billing-api-exception.filter.ts
index 020949e01..444605e1a 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/filters/billing-api-exception.filter.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/filters/billing-api-exception.filter.ts
@@ -17,22 +17,41 @@ export class BillingRestApiExceptionFilter implements ExceptionFilter {
     private readonly httpExceptionHandlerService: HttpExceptionHandlerService,
   ) {}
 
-  catch(exception: BillingException, host: ArgumentsHost) {
+  catch(
+    exception: BillingException | Stripe.errors.StripeError,
+    host: ArgumentsHost,
+  ) {
     const ctx = host.switchToHttp();
     const response = ctx.getResponse<Response>();
 
+    if (exception instanceof Stripe.errors.StripeError) {
+      return this.httpExceptionHandlerService.handleError(
+        {
+          code: BillingExceptionCode.BILLING_STRIPE_ERROR,
+          message: exception.message,
+          name: 'StripeError',
+        },
+        response,
+        400,
+      );
+    }
+
     switch (exception.code) {
       case BillingExceptionCode.BILLING_CUSTOMER_NOT_FOUND:
+      case BillingExceptionCode.BILLING_ACTIVE_SUBSCRIPTION_NOT_FOUND:
+      case BillingExceptionCode.BILLING_SUBSCRIPTION_EVENT_WORKSPACE_NOT_FOUND:
+      case BillingExceptionCode.BILLING_PRODUCT_NOT_FOUND:
+      case BillingExceptionCode.BILLING_PLAN_NOT_FOUND:
         return this.httpExceptionHandlerService.handleError(
           exception,
           response,
           404,
         );
-      case BillingExceptionCode.BILLING_PRODUCT_NOT_FOUND:
+      case BillingExceptionCode.BILLING_METER_EVENT_FAILED:
         return this.httpExceptionHandlerService.handleError(
           exception,
           response,
-          404,
+          400,
         );
       default:
         return this.httpExceptionHandlerService.handleError(