diff --git a/apps/web/pages/api/book/event.ts b/apps/web/pages/api/book/event.ts
index 1c5b3d41d4..e2f88a180e 100644
--- a/apps/web/pages/api/book/event.ts
+++ b/apps/web/pages/api/book/event.ts
@@ -646,8 +646,7 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
 
     results = updateManager.results;
     referencesToCreate = updateManager.referencesToCreate;
-
-    if (results.length > 0 && results.every((res) => !res.success)) {
+    if (results.length > 0 && results.some((res) => !res.success)) {
       const error = {
         errorCode: "BookingReschedulingMeetingFailed",
         message: "Booking Rescheduling failed",
diff --git a/packages/core/CalendarManager.ts b/packages/core/CalendarManager.ts
index 9159dd6c52..b3fbfae1a7 100644
--- a/packages/core/CalendarManager.ts
+++ b/packages/core/CalendarManager.ts
@@ -132,15 +132,19 @@ export const updateEvent = async (
 ): Promise<EventResult> => {
   const uid = getUid(calEvent);
   const calendar = getCalendar(credential);
-  let success = true;
-
+  let success = false;
+  if (bookingRefUid === "") {
+    log.error("updateEvent failed", "bookingRefUid is empty", calEvent, credential);
+  }
   const updatedResult =
     calendar && bookingRefUid
-      ? await calendar.updateEvent(bookingRefUid, calEvent).catch((e) => {
-          log.error("updateEvent failed", e, calEvent);
-          success = false;
-          return undefined;
-        })
+      ? await calendar
+          .updateEvent(bookingRefUid, calEvent)
+          .then(() => (success = true))
+          .catch((e) => {
+            log.error("updateEvent failed", e, calEvent);
+            return undefined;
+          })
       : undefined;
 
   return {
diff --git a/packages/core/EventManager.ts b/packages/core/EventManager.ts
index fdfb1c0c42..6e90a130f1 100644
--- a/packages/core/EventManager.ts
+++ b/packages/core/EventManager.ts
@@ -345,8 +345,13 @@ export default class EventManager {
     booking: PartialBooking
   ): Promise<Array<EventResult>> {
     return async.mapLimit(this.calendarCredentials, 5, async (credential: Credential) => {
+      // HACK:
+      // Right now if two calendars are connected and a booking is created it has two bookingReferences, one is having uid null and the other is having valid uid.
+      // I don't know why yet - But we should work on fixing that. But even after the fix as there can be multiple references in an existing booking the following ref.uid check would still be required
+      // We should ignore the one with uid null, the other one is valid.
+      // Also, we should store(if not already) that which is the calendarCredential for the valid bookingReference, instead of going through all credentials one by one
       const bookingRefUid = booking
-        ? booking.references.filter((ref) => ref.type === credential.type)[0]?.uid
+        ? booking.references.filter((ref) => ref.type === credential.type && !!ref.uid)[0]?.uid
         : null;
 
       return updateEvent(credential, event, bookingRefUid);