diff --git a/apps/web/components/booking/CancelBooking.tsx b/apps/web/components/booking/CancelBooking.tsx
index 0c1189ca9c..7c3021a3a9 100644
--- a/apps/web/components/booking/CancelBooking.tsx
+++ b/apps/web/components/booking/CancelBooking.tsx
@@ -5,7 +5,7 @@ import { useLocale } from "@calcom/lib/hooks/useLocale";
 import { useRefreshData } from "@calcom/lib/hooks/useRefreshData";
 import { collectPageParameters, telemetryEventTypes, useTelemetry } from "@calcom/lib/telemetry";
 import type { RecurringEvent } from "@calcom/types/Calendar";
-import { Button, Icon, TextArea } from "@calcom/ui";
+import { Button, Icon, Label, TextArea } from "@calcom/ui";
 
 type Props = {
   booking: {
@@ -33,6 +33,7 @@ type Props = {
     };
     eventType: unknown;
   };
+  isHost: boolean;
 };
 
 export default function CancelBooking(props: Props) {
@@ -70,7 +71,7 @@ export default function CancelBooking(props: Props) {
       )}
       {!error && (
         <div className="mt-5 sm:mt-6">
-          <label className="text-default font-medium">{t("cancellation_reason")}</label>
+          <Label>{props.isHost ? t("cancellation_reason_host") : t("cancellation_reason")}</Label>
           <TextArea
             data-testid="cancel_reason"
             ref={cancelBookingRef}
@@ -80,6 +81,14 @@ export default function CancelBooking(props: Props) {
             className="mb-4 mt-2 w-full "
             rows={3}
           />
+          {props.isHost ? (
+            <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">
+                {t("notify_attendee_cancellation_reason_warning")}
+              </p>
+            </div>
+          ) : null}
           <div className="flex flex-col-reverse rtl:space-x-reverse ">
             <div className="ml-auto flex w-full space-x-4 ">
               <Button
@@ -90,6 +99,7 @@ export default function CancelBooking(props: Props) {
               </Button>
               <Button
                 data-testid="confirm_cancel"
+                disabled={props.isHost && !cancellationReason}
                 onClick={async () => {
                   setLoading(true);
 
diff --git a/apps/web/modules/bookings/views/bookings-single-view.getServerSideProps.tsx b/apps/web/modules/bookings/views/bookings-single-view.getServerSideProps.tsx
index 93dccd0da0..d0b8eb5a33 100644
--- a/apps/web/modules/bookings/views/bookings-single-view.getServerSideProps.tsx
+++ b/apps/web/modules/bookings/views/bookings-single-view.getServerSideProps.tsx
@@ -163,10 +163,24 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
   });
 
   const userId = session?.user?.id;
-  const isLoggedInUserHost =
-    userId &&
-    (eventType.users.some((user) => user.id === userId) ||
-      eventType.hosts.some(({ user }) => user.id === userId));
+
+  const checkIfUserIsHost = (userId?: number | null) => {
+    if (!userId) return false;
+
+    return (
+      bookingInfo?.user?.id === userId ||
+      eventType.users.some(
+        (user) =>
+          user.id === userId && bookingInfo.attendees.some((attendee) => attendee.email === user.email)
+      ) ||
+      eventType.hosts.some(
+        ({ user }) =>
+          user.id === userId && bookingInfo.attendees.some((attendee) => attendee.email === user.email)
+      )
+    );
+  };
+
+  const isLoggedInUserHost = checkIfUserIsHost(userId);
 
   if (!isLoggedInUserHost) {
     // Removing hidden fields from responses
@@ -195,6 +209,7 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
       userTimeFormat,
       requiresLoginToUpdate,
       rescheduledToUid,
+      isLoggedInUserHost,
     },
   };
 }
diff --git a/apps/web/modules/bookings/views/bookings-single-view.tsx b/apps/web/modules/bookings/views/bookings-single-view.tsx
index a230107db3..d6df67d9be 100644
--- a/apps/web/modules/bookings/views/bookings-single-view.tsx
+++ b/apps/web/modules/bookings/views/bookings-single-view.tsx
@@ -132,7 +132,6 @@ export default function Success(props: PageProps) {
   ) {
     rescheduleLocation = bookingInfo.responses.location.optionValue;
   }
-
   const locationVideoCallUrl: string | undefined = bookingMetadataSchema.parse(
     bookingInfo?.metadata || {}
   )?.videoCallUrl;
@@ -149,6 +148,7 @@ export default function Success(props: PageProps) {
     props?.userTimeFormat ? props.userTimeFormat === 24 : isBrowserLocale24h()
   );
   const { data: session } = useSession();
+  const isHost = props.isLoggedInUserHost;
 
   const [date, setDate] = useState(dayjs.utc(bookingInfo.startTime));
 
@@ -317,7 +317,6 @@ export default function Success(props: PageProps) {
       return t(`needs_to_be_confirmed_or_rejected${titleSuffix}`);
     }
     if (bookingInfo.user) {
-      const isHost = bookingInfo.user.id === session?.user?.id;
       const isAttendee = bookingInfo.attendees.find((attendee) => attendee.email === session?.user?.email);
       const attendee = bookingInfo.attendees[0]?.name || bookingInfo.attendees[0]?.email || "Nameless";
       const host = bookingInfo.user.name || bookingInfo.user.email;
@@ -778,6 +777,7 @@ export default function Success(props: PageProps) {
                             seatReferenceUid={seatReferenceUid}
                             bookingCancelledEventProps={bookingCancelledEventProps}
                             currentUserEmail={currentUserEmail}
+                            isHost={isHost}
                           />
                         </>
                       ))}
diff --git a/apps/web/playwright/booking-pages.e2e.ts b/apps/web/playwright/booking-pages.e2e.ts
index 347d5dc7c7..6d7972e863 100644
--- a/apps/web/playwright/booking-pages.e2e.ts
+++ b/apps/web/playwright/booking-pages.e2e.ts
@@ -175,6 +175,8 @@ test.describe("pro user", () => {
     await page.waitForURL((url) => {
       return url.pathname.startsWith("/booking/");
     });
+
+    await page.locator('[data-testid="cancel_reason"]').fill("Test reason");
     await page.locator('[data-testid="confirm_cancel"]').click();
 
     const cancelledHeadline = page.locator('[data-testid="cancelled-headline"]');
@@ -205,6 +207,7 @@ test.describe("pro user", () => {
     await page.waitForURL((url) => {
       return url.pathname.startsWith("/booking/");
     });
+    await page.locator('[data-testid="cancel_reason"]').fill("Test reason");
     await page.locator('[data-testid="confirm_cancel"]').click();
 
     const cancelledHeadline = page.locator('[data-testid="cancelled-headline"]');
diff --git a/apps/web/playwright/booking-seats.e2e.ts b/apps/web/playwright/booking-seats.e2e.ts
index cb0505a1b3..14a30d8222 100644
--- a/apps/web/playwright/booking-seats.e2e.ts
+++ b/apps/web/playwright/booking-seats.e2e.ts
@@ -228,6 +228,8 @@ test.describe("Reschedule for booking with seats", () => {
       `/booking/${booking.uid}?cancel=true&allRemainingBookings=false&seatReferenceUid=${bookingSeats[0].referenceUid}`
     );
 
+    await page.locator('[data-testid="cancel_reason"]').fill("Test reason");
+
     await page.locator('[data-testid="confirm_cancel"]').click();
 
     await expect(page.locator("text=You are no longer attending this event")).toBeVisible();
@@ -236,6 +238,8 @@ test.describe("Reschedule for booking with seats", () => {
       `/booking/${booking.uid}?cancel=true&allRemainingBookings=false&seatReferenceUid=${bookingSeats[1].referenceUid}`
     );
 
+    await page.locator('[data-testid="cancel_reason"]').fill("Test reason");
+
     // Page should not be 404
     await page.locator('[data-testid="confirm_cancel"]').click();
 
diff --git a/apps/web/playwright/dynamic-booking-pages.e2e.ts b/apps/web/playwright/dynamic-booking-pages.e2e.ts
index bb8fce8e78..137e7b4a1f 100644
--- a/apps/web/playwright/dynamic-booking-pages.e2e.ts
+++ b/apps/web/playwright/dynamic-booking-pages.e2e.ts
@@ -56,6 +56,7 @@ test("dynamic booking", async ({ page, users }) => {
     await page.waitForURL((url) => {
       return url.pathname.startsWith("/booking");
     });
+    await page.locator('[data-testid="cancel_reason"]').fill("Test reason");
     await page.locator('[data-testid="confirm_cancel"]').click();
 
     const cancelledHeadline = page.locator('[data-testid="cancelled-headline"]');
diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index d0450c6497..619e86dab4 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -52,7 +52,9 @@
   "you_can_view_booking_details_with_this_url": "You can view the booking details from this url {{url}} and add the event to your calendar",
   "no_options_available": "No options available",
   "cancellation_reason": "Reason for cancellation (optional)",
+  "cancellation_reason_host": "Reason for cancellation",
   "cancellation_reason_placeholder": "Why are you cancelling?",
+  "notify_attendee_cancellation_reason_warning":"Please note that the cancellation reason will be visible to the attendee.",
   "rejection_reason_placeholder": "Why are you rejecting?",
   "rejection_reason": "Reason for rejecting",
   "rejection_reason_title": "Reject the booking request?",
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index d603a476c1..d2c699c552 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -180,6 +180,13 @@ async function handler(req: CustomRequest) {
     throw new HttpError({ statusCode: 400, message: "User not found" });
   }
 
+  if (!cancellationReason && req.bookingToDelete.userId == userId) {
+    throw new HttpError({
+      statusCode: 400,
+      message: "Cancellation reason is required when you are the host",
+    });
+  }
+
   // If the booking is a seated event and there is no seatReferenceUid we should validate that logged in user is host
   if (bookingToDelete.eventType?.seatsPerTimeSlot && !seatReferenceUid) {
     const userIsHost = bookingToDelete.eventType.hosts.find((host) => {
diff --git a/packages/features/bookings/lib/handleSeats/test/handleSeats.test.ts b/packages/features/bookings/lib/handleSeats/test/handleSeats.test.ts
index 45324d62ef..b2b44588e2 100644
--- a/packages/features/bookings/lib/handleSeats/test/handleSeats.test.ts
+++ b/packages/features/bookings/lib/handleSeats/test/handleSeats.test.ts
@@ -1677,6 +1677,7 @@ describe("handleSeats", () => {
         });
 
         req.userId = organizer.id;
+        req.body.cancellationReason = "test cancellation reason";
 
         await handleCancelBooking(req);
 
@@ -1817,6 +1818,7 @@ describe("handleSeats", () => {
         });
 
         req.userId = organizer.id;
+        req.body.cancellationReason = "test cancellation reason";
 
         await handleCancelBooking(req);
 
@@ -2682,6 +2684,7 @@ describe("handleSeats", () => {
         });
 
         req.userId = organizer.id;
+        req.body.cancellationReason = "test cancellation reason";
 
         await handleCancelBooking(req);