diff --git a/server/src/controllers/PaymentController.js b/server/src/controllers/PaymentController.js
index 661111db..91b85872 100644
--- a/server/src/controllers/PaymentController.js
+++ b/server/src/controllers/PaymentController.js
@@ -13,10 +13,15 @@ const PaymentController = {
     try {
       switch (event.type) {
         case 'payment_intent.succeeded': {
-          const { id, amount_received } = event.data.object;
+          const { id, amount_received, payment_intent } = event.data.object;
+          const user = req.user;
 
           console.log('Handling payment intent');
+          console.log('UserID:', user.id); // Log the userID
+          console.log('PaymentIntent:', payment_intent); // Log the paymentIntent
+
           // update frosh model to have paid successfully
+          await FroshServices.addRetreatPayment(user.id, payment_intent);
           await PaymentServices.updatePayment(id, amount_received);
           break;
         }
@@ -63,16 +68,8 @@ const PaymentController = {
       const user = req.user;
       const count = await PaymentServices.getNonExpiredPaymentsCountForItem('Retreat Ticket');
       if (count < process.env.RETREAT_MAX_TICKETS) {
-        const { url, payment_intent } = await PaymentServices.createCheckoutSession(
-          user.email,
-          'retreat',
-        );
-
-        const frosh = await FroshServices.addRetreatPayment(user, payment_intent);
-        if (!frosh) {
-          res.status(400).send({ message: 'Something went wrong!' });
-        }
-        res.status(200).send({ url });
+        const session = await PaymentServices.createCheckoutSession(user.email, 'retreat', user.id);
+        res.status(200).send({ url: session.url });
       } else {
         res.status(400).send({
           message: 'Sold out! Please check back later in case more tickets become available',
diff --git a/server/src/services/FroshServices.js b/server/src/services/FroshServices.js
index 26451f8e..3ea2c412 100644
--- a/server/src/services/FroshServices.js
+++ b/server/src/services/FroshServices.js
@@ -64,8 +64,10 @@ const FroshServices = {
    * @param {Payment} paymentIntent Payment object from stripe
    * @returns {User} updated user
    */
-  async addRetreatPayment(user, paymentIntent) {
-    return FroshModel.findByIdAndUpdate(user.id, {
+  async addRetreatPayment(userID, paymentIntent) {
+    console.log('Adding retreat payment for userID:', userID);
+    console.log('PaymentIntent:', paymentIntent);
+    return FroshModel.findByIdAndUpdate(userID, {
       $push: {
         payments: [
           {
diff --git a/server/src/services/PaymentServices.js b/server/src/services/PaymentServices.js
index e4f1d3e0..c1e1c7f2 100644
--- a/server/src/services/PaymentServices.js
+++ b/server/src/services/PaymentServices.js
@@ -99,7 +99,7 @@ const PaymentServices = {
    * @return {Promise<Stripe.Checkout.Session & {lastResponse: {headers: {[p: string]: string}; requestId: string; statusCode: number; apiVersion?: string; idempotencyKey?: string; stripeAccount?: string}}>}
    */
   /* istanbul ignore next */
-  async createCheckoutSession(email, type = 'orientation') {
+  async createCheckoutSession(email, type = 'orientation', userId) {
     const products = {
       orientation: {
         priceId: process.env.STRIPE_TICKET_PRICE_ID,
@@ -131,6 +131,9 @@ const PaymentServices = {
       cancel_url: `${process.env.CLIENT_BASE_URL}${
         products[type]?.relativeUrlFailure ?? products['orientation'].relativeUrlFailure
       }`,
+      metadata: {
+        userId, // Add user ID to metadata for webhook processing
+      },
     });
     // } catch (error) {
     //   if (error.raw?.code === 'coupon_expired') {