diff --git a/apps/web/components/booking/CancelBooking.tsx b/apps/web/components/booking/CancelBooking.tsx
index 4591aa92b5..e53a0e7349 100644
--- a/apps/web/components/booking/CancelBooking.tsx
+++ b/apps/web/components/booking/CancelBooking.tsx
@@ -157,8 +157,11 @@ export default function CancelBooking(props: Props) {
 
   const cancellationNoShowFeeWarning = autoChargeNoShowFee();
 
+  const isCancellationUserHost =
+    props.isHost || bookingCancelledEventProps.organizer.email === currentUserEmail;
+
   const hostMissingCancellationReason =
-    props.isHost &&
+    isCancellationUserHost &&
     (!cancellationReason?.trim() || (props.internalNotePresets.length > 0 && !internalNote?.id));
   const cancellationNoShowFeeNotAcknowledged =
     !props.isHost && cancellationNoShowFeeWarning && !acknowledgeCancellationNoShowFee;
@@ -211,7 +214,7 @@ export default function CancelBooking(props: Props) {
             </>
           )}
 
-          <Label>{props.isHost ? t("cancellation_reason_host") : t("cancellation_reason")}</Label>
+          <Label>{isCancellationUserHost ? t("cancellation_reason_host") : t("cancellation_reason")}</Label>
 
           <TextArea
             data-testid="cancel_reason"
@@ -222,7 +225,7 @@ export default function CancelBooking(props: Props) {
             className="mb-4 mt-2 w-full "
             rows={3}
           />
-          {props.isHost ? (
+          {isCancellationUserHost ? (
             <div className="-mt-2 mb-4 flex items-center gap-2">
               <Icon name="info" className="text-subtle h-4 w-4" />
               <p className="text-default text-subtle text-sm leading-none">
@@ -296,11 +299,13 @@ export default function CancelBooking(props: Props) {
                     });
                     refreshData();
                   } else {
+                    const data = await res.json();
                     setLoading(false);
                     setError(
-                      `${t("error_with_status_code_occured", { status: res.status })} ${t(
-                        "please_try_again"
-                      )}`
+                      data.message ||
+                        `${t("error_with_status_code_occured", { status: res.status })} ${t(
+                          "please_try_again"
+                        )}`
                     );
                   }
                 }}
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index e70423e794..92dc9f4c0e 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -114,7 +114,10 @@ async function handler(input: CancelBookingInput) {
     });
   }
 
-  if (!platformClientId && !cancellationReason?.trim() && bookingToDelete.userId == userId) {
+  const isCancellationUserHost =
+    bookingToDelete.userId == userId || bookingToDelete.user.email === cancelledBy;
+
+  if (!platformClientId && !cancellationReason?.trim() && isCancellationUserHost) {
     throw new HttpError({
       statusCode: 400,
       message: "Cancellation reason is required when you are the host",
diff --git a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
index b8fd087057..0ad54ff65d 100644
--- a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
+++ b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
@@ -132,6 +132,7 @@ describe("Cancel Booking", () => {
         id: idOfBookingToBeCancelled,
         uid: uidOfBookingToBeCancelled,
         cancelledBy: organizer.email,
+        cancellationReason: "No reason",
       },
     });
 
@@ -261,6 +262,7 @@ describe("Cancel Booking", () => {
         id: idOfBookingToBeCancelled,
         uid: uidOfBookingToBeCancelled,
         cancelledBy: organizer.email,
+        cancellationReason: "No reason",
       },
     });
 
@@ -510,6 +512,74 @@ describe("Cancel Booking", () => {
     ).rejects.toThrow("Cannot cancel a booking that has already ended");
   });
 
+  test("Should block canceling bookings without a cancellation reason when cancelledBy is set to the host", async () => {
+    const handleCancelBooking = (await import("@calcom/features/bookings/lib/handleCancelBooking")).default;
+
+    const booker = getBooker({
+      email: "booker@example.com",
+      name: "Booker",
+    });
+
+    const organizer = getOrganizer({
+      name: "Organizer",
+      email: "organizer@example.com",
+      id: 101,
+      schedules: [TestData.schedules.IstWorkHours],
+      credentials: [getGoogleCalendarCredential()],
+      selectedCalendars: [TestData.selectedCalendars.google],
+    });
+
+    const uidOfBookingToBeCancelled = "cancelled-booking";
+    const idOfBookingToBeCancelled = 3040;
+    const { dateString: plus1DateString } = getDate({ dateIncrement: 1 });
+
+    await createBookingScenario(
+      getScenarioData({
+        eventTypes: [
+          {
+            id: 1,
+            slotInterval: 30,
+            length: 30,
+            users: [
+              {
+                id: 101,
+              },
+            ],
+          },
+        ],
+        bookings: [
+          {
+            id: idOfBookingToBeCancelled,
+            uid: uidOfBookingToBeCancelled,
+            eventTypeId: 1,
+            userId: 101,
+            responses: {
+              email: booker.email,
+              name: booker.name,
+              location: { optionValue: "", value: BookingLocations.CalVideo },
+            },
+            status: BookingStatus.ACCEPTED,
+            startTime: `${plus1DateString}T05:00:00.000Z`,
+            endTime: `${plus1DateString}T05:30:00.000Z`,
+          },
+        ],
+        organizer,
+        apps: [TestData.apps["daily-video"]],
+      })
+    );
+
+    // This should throw an error with current implementation
+    await expect(
+      handleCancelBooking({
+        bookingData: {
+          id: idOfBookingToBeCancelled,
+          uid: uidOfBookingToBeCancelled,
+          cancelledBy: organizer.email,
+        },
+      })
+    ).rejects.toThrow("Cancellation reason is required when you are the host");
+  });
+
   test("Should not charge cancellation fee when organizer cancels booking", async () => {
     const handleCancelBooking = (await import("@calcom/features/bookings/lib/handleCancelBooking")).default;
 
@@ -615,6 +685,7 @@ describe("Cancel Booking", () => {
         id: idOfBookingToBeCancelled,
         uid: uidOfBookingToBeCancelled,
         cancelledBy: organizer.email,
+        cancellationReason: "No reason",
       },
     });
 
@@ -747,6 +818,7 @@ describe("Cancel Booking", () => {
         id: idOfBookingToBeCancelled,
         uid: uidOfBookingToBeCancelled,
         cancelledBy: organizer.email,
+        cancellationReason: "No reason",
       },
     });