diff --git a/packages/features/ee/round-robin/roundRobinManualReassignment.test.ts b/packages/features/ee/round-robin/roundRobinManualReassignment.test.ts
index 88bc6d542e..ea8e76a68d 100644
--- a/packages/features/ee/round-robin/roundRobinManualReassignment.test.ts
+++ b/packages/features/ee/round-robin/roundRobinManualReassignment.test.ts
@@ -247,4 +247,78 @@ describe("roundRobinManualReassignment test", () => {
     expect(attendees.some((attendee) => attendee.email === currentRRHost.email)).toBe(false);
     expect(attendees.some((attendee) => attendee.email === newHost.email)).toBe(true);
   });
+
+  test("sends cancellation email to previous RR host when reassigning", async ({ emails }) => {
+    const roundRobinManualReassignment = (await import("./roundRobinManualReassignment")).default;
+    const EventManager = (await import("@calcom/core/EventManager")).default;
+
+    const eventManagerSpy = vi.spyOn(EventManager.prototype as any, "reschedule");
+    eventManagerSpy.mockResolvedValue({ referencesToCreate: [] });
+
+    const sendRoundRobinCancelledEmailsAndSMSSpy = vi.spyOn(
+      await import("@calcom/emails"),
+      "sendRoundRobinCancelledEmailsAndSMS"
+    );
+
+    const users = testUsers;
+    const originalHost = users[0];
+    const previousRRHost = users[1];
+    const newHost = users[2];
+
+    const { dateString: dateStringPlusOne } = getDate({ dateIncrement: 1 });
+
+    const bookingToReassignUid = "booking-to-reassign-with-previous-rr-host";
+
+    await createBookingScenario(
+      getScenarioData({
+        eventTypes: [
+          {
+            id: 1,
+            slug: "round-robin-event",
+            schedulingType: SchedulingType.ROUND_ROBIN,
+            length: 45,
+            users: users.map((user) => ({ id: user.id })),
+            hosts: users.map((user) => ({ userId: user.id, isFixed: false })),
+          },
+        ],
+        bookings: [
+          {
+            id: 124,
+            eventTypeId: 1,
+            userId: originalHost.id,
+            uid: bookingToReassignUid,
+            status: BookingStatus.ACCEPTED,
+            startTime: `${dateStringPlusOne}T05:00:00.000Z`,
+            endTime: `${dateStringPlusOne}T05:15:00.000Z`,
+            attendees: [
+              getMockBookingAttendee({
+                id: 2,
+                name: "attendee",
+                email: "attendee@test.com",
+                locale: "en",
+                timeZone: "Asia/Kolkata",
+              }),
+              getMockBookingAttendee({
+                id: previousRRHost.id,
+                name: previousRRHost.name,
+                email: previousRRHost.email,
+                locale: "en",
+                timeZone: previousRRHost.timeZone,
+              }),
+            ],
+          },
+        ],
+        organizer: originalHost,
+        usersApartFromOrganizer: users.slice(1),
+      })
+    );
+
+    await roundRobinManualReassignment({
+      bookingId: 124,
+      newUserId: newHost.id,
+      orgId: null,
+    });
+
+    expect(sendRoundRobinCancelledEmailsAndSMSSpy).toHaveBeenCalledTimes(1);
+  });
 });
diff --git a/packages/features/ee/round-robin/roundRobinManualReassignment.ts b/packages/features/ee/round-robin/roundRobinManualReassignment.ts
index 94dd8484aa..7117dbe693 100644
--- a/packages/features/ee/round-robin/roundRobinManualReassignment.ts
+++ b/packages/features/ee/round-robin/roundRobinManualReassignment.ts
@@ -104,6 +104,24 @@ export const roundRobinManualReassignment = async ({
   const newUserT = await getTranslation(newUser.locale || "en", "common");
   const originalOrganizerT = await getTranslation(originalOrganizer.locale || "en", "common");
 
+  const roundRobinHosts = eventType.hosts.filter((host) => !host.isFixed);
+
+  const attendeeEmailsSet = new Set(booking.attendees.map((attendee) => attendee.email));
+
+  // Find the current round robin host assigned
+  const previousRRHost = (() => {
+    for (const host of roundRobinHosts) {
+      if (host.user.id === booking.userId) {
+        return host.user;
+      }
+      if (attendeeEmailsSet.has(host.user.email)) {
+        return host.user;
+      }
+    }
+  })();
+
+  const previousRRHostT = await getTranslation(previousRRHost?.locale || "en", "common");
+
   if (hasOrganizerChanged) {
     const bookingResponses = booking.responses;
     const responseSchema = getBookingResponsesSchema({
@@ -166,24 +184,38 @@ export const roundRobinManualReassignment = async ({
     hasOrganizerChanged,
   });
 
+  const organizer = hasOrganizerChanged ? newUser : booking.user ?? newUser;
+
+  const organizerT = await getTranslation(organizer?.locale || "en", "common");
+
   const teamMembers = await getTeamMembers({
     eventTypeHosts,
     attendees: booking.attendees,
-    organizer: newUser,
-    previousHost: originalOrganizer,
+    organizer,
+    previousHost: previousRRHost || null,
     reassignedHost: newUser,
   });
 
-  const attendeePromises = booking.attendees.map(async (attendee) => ({
-    email: attendee.email,
-    name: attendee.name,
-    timeZone: attendee.timeZone,
-    language: {
-      translate: await getTranslation(attendee.locale ?? "en", "common"),
-      locale: attendee.locale ?? "en",
-    },
-    phoneNumber: attendee.phoneNumber || undefined,
-  }));
+  const attendeePromises = [];
+  for (const attendee of booking.attendees) {
+    if (
+      attendee.email === newUser.email ||
+      attendee.email === previousRRHost?.email ||
+      teamMembers.some((member) => member.email === attendee.email)
+    ) {
+      continue;
+    }
+
+    attendeePromises.push(
+      getTranslation(attendee.locale ?? "en", "common").then((tAttendee) => ({
+        email: attendee.email,
+        name: attendee.name,
+        timeZone: attendee.timeZone,
+        language: { translate: tAttendee, locale: attendee.locale ?? "en" },
+        phoneNumber: attendee.phoneNumber || undefined,
+      }))
+    );
+  }
 
   const attendeeList = await Promise.all(attendeePromises);
 
@@ -194,10 +226,10 @@ export const roundRobinManualReassignment = async ({
     startTime: dayjs(booking.startTime).utc().format(),
     endTime: dayjs(booking.endTime).utc().format(),
     organizer: {
-      email: newUser.email,
-      name: newUser.name || "",
-      timeZone: newUser.timeZone,
-      language: { translate: newUserT, locale: newUser.locale || "en" },
+      email: organizer.email,
+      name: organizer.name || "",
+      timeZone: organizer.timeZone,
+      language: { translate: organizerT, locale: organizer.locale || "en" },
     },
     attendees: attendeeList,
     uid: booking.uid,
@@ -242,8 +274,10 @@ export const roundRobinManualReassignment = async ({
     newReferencesToCreate,
   });
 
+  const { cancellationReason, ...evtWithoutCancellationReason } = evt;
+
   // Send emails
-  await sendRoundRobinScheduledEmailsAndSMS(evt, [
+  await sendRoundRobinScheduledEmailsAndSMS(evtWithoutCancellationReason, [
     {
       ...newUser,
       name: newUser.name || "",
@@ -262,19 +296,21 @@ export const roundRobinManualReassignment = async ({
     language: { translate: originalOrganizerT, locale: originalOrganizer.locale || "en" },
   };
 
-  await sendRoundRobinCancelledEmailsAndSMS(
-    cancelledEvt,
-    [
-      {
-        ...originalOrganizer,
-        name: originalOrganizer.name || "",
-        username: originalOrganizer.username || "",
-        timeFormat: getTimeFormatStringFromUserTimeFormat(originalOrganizer.timeFormat),
-        language: { translate: originalOrganizerT, locale: originalOrganizer.locale || "en" },
-      },
-    ],
-    eventType?.metadata as EventTypeMetadata
-  );
+  if (previousRRHost) {
+    await sendRoundRobinCancelledEmailsAndSMS(
+      cancelledEvt,
+      [
+        {
+          ...previousRRHost,
+          name: previousRRHost.name || "",
+          username: previousRRHost.username || "",
+          timeFormat: getTimeFormatStringFromUserTimeFormat(previousRRHost.timeFormat),
+          language: { translate: previousRRHostT, locale: previousRRHost.locale || "en" },
+        },
+      ],
+      eventType?.metadata as EventTypeMetadata
+    );
+  }
 
   if (hasOrganizerChanged) {
     // Handle changing workflows with organizer
diff --git a/packages/features/ee/round-robin/roundRobinReassignment.ts b/packages/features/ee/round-robin/roundRobinReassignment.ts
index 80a6409093..b4fdc71eb4 100644
--- a/packages/features/ee/round-robin/roundRobinReassignment.ts
+++ b/packages/features/ee/round-robin/roundRobinReassignment.ts
@@ -151,17 +151,6 @@ export const roundRobinReassignment = async ({
     reassignedHost: reassignedRRHost,
   });
 
-  // Assume the RR host was labelled as a team member
-  if (reassignedRRHost.email !== organizer.email) {
-    teamMembers.push({
-      id: reassignedRRHost.id,
-      email: reassignedRRHost.email,
-      name: reassignedRRHost.name || "",
-      timeZone: reassignedRRHost.timeZone,
-      language: { translate: reassignedRRHostT, locale: reassignedRRHost.locale ?? "en" },
-    });
-  }
-
   const attendeePromises = [];
   for (const attendee of booking.attendees) {
     if (