diff --git a/apps/api/v2/src/ee/bookings/2024-04-15/controllers/bookings.controller.ts b/apps/api/v2/src/ee/bookings/2024-04-15/controllers/bookings.controller.ts
index 7e21b011ff..e02e617577 100644
--- a/apps/api/v2/src/ee/bookings/2024-04-15/controllers/bookings.controller.ts
+++ b/apps/api/v2/src/ee/bookings/2024-04-15/controllers/bookings.controller.ts
@@ -232,6 +232,15 @@ export class BookingsController_2024_04_15 {
     }
 
     if (bookingUid) {
+      const { bookingInfo } = await getBookingInfo(bookingUid);
+      if (!bookingInfo) {
+        throw new NotFoundException(`Booking with UID=${bookingUid} does not exist.`);
+      }
+      if (bookingInfo.status === "CANCELLED") {
+        throw new BadRequestException(
+          `Can't cancel booking with uid=${bookingUid} because it has been cancelled already. Please provide uid of a booking that is not cancelled.`
+        );
+      }
       try {
         req.body.uid = bookingUid;
         const bookingRequest = await this.createNextApiBookingRequest(req, oAuthClientId, undefined, isEmbed);
diff --git a/apps/api/v2/src/ee/bookings/2024-08-13/controllers/e2e/user-bookings.e2e-spec.ts b/apps/api/v2/src/ee/bookings/2024-08-13/controllers/e2e/user-bookings.e2e-spec.ts
index e57b2a93f4..266eafca18 100644
--- a/apps/api/v2/src/ee/bookings/2024-08-13/controllers/e2e/user-bookings.e2e-spec.ts
+++ b/apps/api/v2/src/ee/bookings/2024-08-13/controllers/e2e/user-bookings.e2e-spec.ts
@@ -2553,6 +2553,59 @@ describe("Bookings Endpoints 2024-08-13", () => {
       });
     });
 
+    describe("cant't cancel already cancelled booking", () => {
+      it("should not be able to cancel alraedy cancelled booking", async () => {
+        const cancelledBooking = await bookingsRepositoryFixture.create({
+          status: "CANCELLED",
+          user: {
+            connect: {
+              id: user.id,
+            },
+          },
+          startTime: new Date(Date.UTC(2050, 0, 8, 13, 0, 0)),
+          endTime: new Date(Date.UTC(2050, 0, 8, 14, 0, 0)),
+          title: "peer coding lets goo",
+          uid: `cancelled-booking-${randomString()}`,
+          eventType: {
+            connect: {
+              id: eventTypeId,
+            },
+          },
+          location: "integrations:daily",
+          customInputs: {},
+          metadata: {},
+          responses: {
+            name: "Oldie",
+            email: "oldie@gmail.com",
+          },
+          attendees: {
+            create: {
+              email: "oldie@gmail.com",
+              name: "Oldie",
+              locale: "lv",
+              timeZone: "Europe/Rome",
+            },
+          },
+        });
+
+        const body: CancelBookingInput_2024_08_13 = {
+          cancellationReason: "Going on a vacation",
+        };
+
+        const response = await request(app.getHttpServer())
+          .post(`/v2/bookings/${cancelledBooking.uid}/cancel`)
+          .send(body)
+          .set(CAL_API_VERSION_HEADER, VERSION_2024_08_13)
+          .set(X_CAL_CLIENT_ID, oAuthClient.id)
+          .expect(400);
+
+        expect(response.body.error.message).toEqual(
+          `Can't cancel booking with uid=${cancelledBooking.uid} because it has been cancelled already. Please provide uid of a booking that is not cancelled.`
+        );
+        await bookingsRepositoryFixture.deleteById(cancelledBooking.id);
+      });
+    });
+
     describe("calendar events", () => {
       beforeEach(() => {
         jest.restoreAllMocks();
diff --git a/apps/api/v2/src/ee/bookings/2024-08-13/services/input.service.ts b/apps/api/v2/src/ee/bookings/2024-08-13/services/input.service.ts
index 9c177eaeee..e6c19b2613 100644
--- a/apps/api/v2/src/ee/bookings/2024-08-13/services/input.service.ts
+++ b/apps/api/v2/src/ee/bookings/2024-08-13/services/input.service.ts
@@ -711,6 +711,12 @@ export class InputBookingsService_2024_08_13 {
       throw new NotFoundException(`Booking with uid=${bookingUid} not found`);
     }
 
+    if (booking.status === "CANCELLED") {
+      throw new BadRequestException(
+        `Can't cancel booking with uid=${bookingUid} because it has been cancelled already. Please provide uid of a booking that is not cancelled.`
+      );
+    }
+
     const oAuthClientParams = booking.eventTypeId
       ? await this.platformBookingsService.getOAuthClientParams(booking.eventTypeId)
       : undefined;
diff --git a/packages/features/bookings/lib/getBookingToDelete.ts b/packages/features/bookings/lib/getBookingToDelete.ts
index 590d445075..e218ec254a 100644
--- a/packages/features/bookings/lib/getBookingToDelete.ts
+++ b/packages/features/bookings/lib/getBookingToDelete.ts
@@ -100,6 +100,7 @@ export async function getBookingToDelete(id: number | undefined, uid: string | u
       responses: true,
       iCalUID: true,
       iCalSequence: true,
+      status: true,
     },
   });
 }
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index 4ded8fb2a5..6ed8d3de75 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -89,6 +89,19 @@ async function handler(input: CancelBookingInput) {
     arePlatformEmailsEnabled,
   } = input;
 
+  /**
+   * Important: We prevent cancelling an already cancelled booking.
+   * A booking could have been CANCELLED due to a reschedule,
+   * in which case we simply update the existing calendar event and meeting.
+   * We want to avoid deleting them by a subsequent cancellation attempt.
+   */
+  if (bookingToDelete.status === BookingStatus.CANCELLED) {
+    throw new HttpError({
+      statusCode: 400,
+      message: "This booking has already been cancelled.",
+    });
+  }
+
   if (!bookingToDelete.userId || !bookingToDelete.user) {
     throw new HttpError({ statusCode: 400, message: "User not found" });
   }