diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index 0f6213c745..6814596755 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -1307,6 +1307,7 @@
   "do_this": "Do this",
   "turn_off": "Turn off",
   "turn_on": "Turn on",
+  "cancelled_bookings_cannot_be_rescheduled":"Cancelled bookings cannot be rescheduled",
   "settings_updated_successfully": "Settings updated successfully",
   "error_updating_settings": "Error updating settings",
   "personal_cal_url": "My personal {{appName}} URL",
diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index 2ec81f8a5c..114dcb16e5 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -1078,6 +1078,13 @@ async function handler(
     if (!originalRescheduledBooking) {
       throw new HttpError({ statusCode: 404, message: "Could not find original booking" });
     }
+
+    if (
+      originalRescheduledBooking.status === BookingStatus.CANCELLED &&
+      !originalRescheduledBooking.rescheduled
+    ) {
+      throw new HttpError({ statusCode: 403, message: ErrorCode.CancelledBookingsCannotBeRescheduled });
+    }
   }
 
   //checks what users are available
diff --git a/packages/lib/errorCodes.ts b/packages/lib/errorCodes.ts
index 07c51ae693..e7320a5726 100644
--- a/packages/lib/errorCodes.ts
+++ b/packages/lib/errorCodes.ts
@@ -6,4 +6,5 @@ export enum ErrorCode {
   AlreadySignedUpForBooking = "already_signed_up_for_this_booking_error",
   HostsUnavailableForBooking = "hosts_unavailable_for_booking",
   EventTypeNotFound = "event_type_not_found_error",
+  CancelledBookingsCannotBeRescheduled = "cancelled_bookings_cannot_be_rescheduled",
 }