diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index 550504298e..cb04e6f34d 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -1084,7 +1084,7 @@ async function handler(
             await sendRescheduledEmails({
               ...copyEvent,
               additionalNotes, // Resets back to the additionalNote input and not the override value
-              cancellationReason: "$RCH$" + rescheduleReason ? rescheduleReason : "", // Removable code prefix to differentiate cancellation from rescheduling for email
+              cancellationReason: "$RCH$" + (rescheduleReason ? rescheduleReason : ""), // Removable code prefix to differentiate cancellation from rescheduling for email
             });
           }
           const resultBooking = await resultBookingQuery(newBooking.id);
@@ -1189,7 +1189,7 @@ async function handler(
         await sendRescheduledEmails({
           ...copyEvent,
           additionalNotes, // Resets back to the additionalNote input and not the override value
-          cancellationReason: "$RCH$" + rescheduleReason ? rescheduleReason : "", // Removable code prefix to differentiate cancellation from rescheduling for email
+          cancellationReason: "$RCH$" + (rescheduleReason ? rescheduleReason : ""), // Removable code prefix to differentiate cancellation from rescheduling for email
         });
 
         // Update the old booking with the cancelled status
@@ -1519,6 +1519,9 @@ async function handler(
       };
       newBookingData["paid"] = originalRescheduledBooking.paid;
       newBookingData["fromReschedule"] = originalRescheduledBooking.uid;
+      if (originalRescheduledBooking.uid) {
+        newBookingData.cancellationReason = rescheduleReason;
+      }
       if (newBookingData.attendees?.createMany?.data) {
         // Reschedule logic with booking with seats
         if (eventType?.seatsPerTimeSlot && bookerEmail) {
@@ -1733,7 +1736,7 @@ async function handler(
           ...copyEvent,
           additionalInformation: metadata,
           additionalNotes, // Resets back to the additionalNote input and not the override value
-          cancellationReason: "$RCH$" + rescheduleReason ? rescheduleReason : "", // Removable code prefix to differentiate cancellation from rescheduling for email
+          cancellationReason: "$RCH$" + (rescheduleReason ? rescheduleReason : ""), // Removable code prefix to differentiate cancellation from rescheduling for email
         });
       }
     }