diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index f64ed8d7e8b5cb..243b3035ff68af 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -429,6 +429,8 @@ async function handler(input: CancelBookingInput, dependencies?: Dependencies) {
       isPlatformManagedUserBooking: bookingToDelete.user.isPlatformManaged,
     } satisfies HandleCancelBookingResponse;
 
+  const parsedMetadata = bookingMetadataSchema.safeParse(bookingToDelete.metadata || {});
+
   const { assignmentReason: _emailAssignmentReason, ...evtWithoutAssignmentReason } = evt;
   const promises = webhooks.map((webhook) =>
     sendPayload(webhook.secret, eventTrigger, new Date().toISOString(), webhook, {
@@ -438,6 +440,7 @@ async function handler(input: CancelBookingInput, dependencies?: Dependencies) {
       smsReminderNumber: bookingToDelete.smsReminderNumber || undefined,
       cancelledBy: cancelledBy,
       requestReschedule: false,
+      ...(parsedMetadata.success && parsedMetadata.data ? { metadata: parsedMetadata.data } : {}),
     }).catch((e) => {
       logger.error(
         `Error executing webhook for event: ${eventTrigger}, URL: ${webhook.subscriberUrl}, bookingId: ${evt.bookingId}, bookingUid: ${evt.uid}`,
@@ -448,7 +451,6 @@ async function handler(input: CancelBookingInput, dependencies?: Dependencies) {
   await Promise.all(promises);
 
   const workflows = await getAllWorkflowsFromEventType(bookingToDelete.eventType, bookingToDelete.userId);
-  const parsedMetadata = bookingMetadataSchema.safeParse(bookingToDelete.metadata || {});
 
   const creditService = new CreditService();
 
diff --git a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
index 9bbe4784126ece..3d76ce4837a610 100644
--- a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
+++ b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
@@ -141,6 +141,9 @@ describe("Cancel Booking", () => {
       organizer,
       location: BookingLocations.CalVideo,
       subscriberUrl: "http://my-webhook.example.com",
+      metadata: {
+        videoCallUrl: "https://existing-daily-video-call-url.example.com",
+      },
       payload: {
         cancelledBy: organizer.email,
         organizer: {
@@ -271,6 +274,9 @@ describe("Cancel Booking", () => {
       organizer,
       location: BookingLocations.CalVideo,
       subscriberUrl: "http://my-webhook.example.com",
+      metadata: {
+        videoCallUrl: "https://existing-daily-video-call-url.example.com",
+      },
       payload: {
         cancelledBy: organizer.email,
         organizer: {
@@ -375,6 +381,9 @@ describe("Cancel Booking", () => {
             status: BookingStatus.ACCEPTED,
             startTime: `${plus1DateString}T05:00:00.000Z`,
             endTime: `${plus1DateString}T05:30:00.000Z`,
+            metadata: {
+              myCustomKey: "myCustomValue",
+            },
             attendees: [
               {
                 email: hostAttendee.email,
@@ -423,6 +432,9 @@ describe("Cancel Booking", () => {
       organizer,
       location: BookingLocations.CalVideo,
       subscriberUrl: "http://my-webhook.example.com",
+      metadata: {
+        myCustomKey: "myCustomValue",
+      },
       payload: {
         cancelledBy: organizer.email,
         organizer: {
@@ -1180,6 +1192,9 @@ describe("Cancel Booking", () => {
       },
       location: BookingLocations.CalVideo,
       subscriberUrl: "http://my-webhook.example.com",
+      metadata: {
+        videoCallUrl: "https://existing-daily-video-call-url.example.com",
+      },
       payload: {
         cancelledBy: organizer.email,
         organizer: {
diff --git a/packages/testing/src/lib/bookingScenario/expects.ts b/packages/testing/src/lib/bookingScenario/expects.ts
index f4c180e51cf398..0a98a317bbde33 100644
--- a/packages/testing/src/lib/bookingScenario/expects.ts
+++ b/packages/testing/src/lib/bookingScenario/expects.ts
@@ -1152,12 +1152,14 @@ export function expectBookingCancelledWebhookToHaveBeenFired({
   location,
   subscriberUrl,
   payload,
+  metadata,
 }: {
   organizer: { email: string; name: string; username?: string; usernameInOrg?: string };
   booker: { email: string; name: string };
   subscriberUrl: string;
   location: string;
   payload?: Record<string, unknown>;
+  metadata?: Record<string, unknown> | null;
 }) {
   const organizerPayload = {
     username: organizer.username,
@@ -1169,7 +1171,7 @@ export function expectBookingCancelledWebhookToHaveBeenFired({
     payload: {
       ...payload,
       organizer: organizerPayload,
-      metadata: null,
+      ...(metadata !== undefined ? { metadata } : {}),
       responses: {
         name: {
           label: "name",