diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index 47c45c312e..ce193db7a2 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -1220,8 +1220,10 @@ async function handler(
     eventType.schedulingType === SchedulingType.ROUND_ROBIN &&
     originalRescheduledBooking.userId !== evt.organizer.id;
 
-  const isLocationChanged =
-    !!originalRescheduledBooking && originalRescheduledBooking.location !== evt.location;
+  const isBookingRequestedReschedule =
+    !!originalRescheduledBooking &&
+    !!originalRescheduledBooking.rescheduled &&
+    originalRescheduledBooking.status === BookingStatus.CANCELLED;
 
   let results: EventResult<AdditionalInformation & { url?: string; iCalUID?: string }>[] = [];
   let referencesToCreate: PartialReference[] = [];
@@ -1411,7 +1413,8 @@ async function handler(
       originalRescheduledBooking.uid,
       undefined,
       changedOrganizer,
-      previousHostDestinationCalendar
+      previousHostDestinationCalendar,
+      isBookingRequestedReschedule
     );
     // This gets overridden when updating the event - to check if notes have been hidden or not. We just reset this back
     // to the default description when we are sending the emails.
diff --git a/packages/lib/EventManager.ts b/packages/lib/EventManager.ts
index ac77fd7fb2..553390ab3b 100644
--- a/packages/lib/EventManager.ts
+++ b/packages/lib/EventManager.ts
@@ -449,7 +449,8 @@ export default class EventManager {
     rescheduleUid: string,
     newBookingId?: number,
     changedOrganizer?: boolean,
-    previousHostDestinationCalendar?: DestinationCalendar[] | null
+    previousHostDestinationCalendar?: DestinationCalendar[] | null,
+    isBookingRequestedReschedule?: boolean
   ): Promise<CreateUpdateResult> {
     const originalEvt = processLocation(event);
     const evt = cloneDeep(originalEvt);
@@ -501,7 +502,9 @@ export default class EventManager {
 
     const results: Array<EventResult<Event>> = [];
     const updatedBookingReferences: Array<PartialReference> = [];
-    const isLocationChanged = evt.location && booking.location && evt.location !== booking.location;
+    const isLocationChanged = !!evt.location && !!booking.location && evt.location !== booking.location;
+    const shouldUpdateBookingReferences =
+      !!changedOrganizer || isLocationChanged || !!isBookingRequestedReschedule;
 
     if (evt.requiresConfirmation) {
       log.debug("RescheduleRequiresConfirmation: Deleting Event and Meeting for previous booking");
@@ -525,7 +528,7 @@ export default class EventManager {
         updatedBookingReferences.push(...createdEvent.referencesToCreate);
       } else {
         // If the reschedule doesn't require confirmation, we can "update" the events and meetings to new time.
-        if (isLocationChanged) {
+        if (isLocationChanged || isBookingRequestedReschedule) {
           const updatedLocation = await this.updateLocation(evt, booking);
           results.push(...updatedLocation.results);
           updatedBookingReferences.push(...updatedLocation.referencesToCreate);
@@ -577,8 +580,7 @@ export default class EventManager {
 
     return {
       results,
-      referencesToCreate:
-        changedOrganizer || isLocationChanged ? updatedBookingReferences : [...booking.references],
+      referencesToCreate: shouldUpdateBookingReferences ? updatedBookingReferences : [...booking.references],
     };
   }
 
diff --git a/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts b/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
index 2b3b6521c2..eb1fb4c43c 100644
--- a/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
+++ b/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
@@ -251,7 +251,7 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
           })
         );
         return calendar?.deleteEvent(bookingRef.uid, builder.calendarEvent, bookingRef.externalCalendarId);
-      } else if (bookingRef.type.endsWith("_video") && bookingRef.type !== "daily_video") {
+      } else if (bookingRef.type.endsWith("_video")) {
         return deleteMeeting(
           getDelegationCredentialOrRegularCredential({
             credentials,