diff --git a/apps/web/components/dialog/ReassignDialog.tsx b/apps/web/components/dialog/ReassignDialog.tsx
index 20d2766e2b..e966c397ac 100644
--- a/apps/web/components/dialog/ReassignDialog.tsx
+++ b/apps/web/components/dialog/ReassignDialog.tsx
@@ -135,7 +135,13 @@ export const ReassignDialog = ({ isOpenDialog, setIsOpenDialog, teamId, bookingI
     },
   });
 
-  const [showConfirmation, setShowConfirmation] = useState(false);
+  const [confirmationModal, setConfirmationModal] = useState<{
+    show: boolean;
+    membersStatus: "unavailable" | "available" | null;
+  }>({
+    show: false,
+    membersStatus: null,
+  });
 
   const handleSubmit = (values: FormValues) => {
     if (values.reassignType === "round_robin") {
@@ -143,13 +149,10 @@ export const ReassignDialog = ({ isOpenDialog, setIsOpenDialog, teamId, bookingI
     } else {
       if (values.teamMemberId) {
         const selectedMember = teamMemberOptions?.find((member) => member.value === values.teamMemberId);
-        if (selectedMember && selectedMember.status === "unavailable") {
-          setShowConfirmation(true);
-        } else {
-          roundRobinManualReassignMutation.mutate({
-            bookingId,
-            teamMemberId: values.teamMemberId,
-            reassignReason: values.reassignReason,
+        if (selectedMember) {
+          setConfirmationModal({
+            show: true,
+            membersStatus: selectedMember.status as "available" | "unavailable",
           });
         }
       }
@@ -263,10 +266,16 @@ export const ReassignDialog = ({ isOpenDialog, setIsOpenDialog, teamId, bookingI
         </DialogContent>
       </Dialog>
 
-      <Dialog open={showConfirmation} onOpenChange={setShowConfirmation}>
+      <Dialog
+        open={confirmationModal?.show}
+        onOpenChange={(open) => setConfirmationModal({ ...confirmationModal, show: open })}>
         <ConfirmationDialogContent
-          variety="warning"
-          title={t("confirm_reassign_unavailable")}
+          variety={confirmationModal?.membersStatus === "unavailable" ? "warning" : "success"}
+          title={
+            confirmationModal?.membersStatus === "unavailable"
+              ? t("confirm_reassign_unavailable")
+              : t("confirm_reassign_available")
+          }
           confirmBtnText={t("yes_reassign")}
           cancelBtnText={t("cancel")}
           onConfirm={() => {
@@ -279,14 +288,21 @@ export const ReassignDialog = ({ isOpenDialog, setIsOpenDialog, teamId, bookingI
               teamMemberId,
               reassignReason: form.getValues("reassignReason"),
             });
-            setShowConfirmation(false);
+            setConfirmationModal({
+              show: false,
+              membersStatus: null,
+            });
           }}>
-          <p className="mb-4">{t("reassign_unavailable_team_member_description")}</p>
+          <p className="mb-4">
+            {confirmationModal?.membersStatus === "unavailable"
+              ? t("reassign_unavailable_team_member_description")
+              : t("reassign_available_team_member_description")}
+          </p>
           <TextAreaField
             name="reassignReason"
             label={t("reassign_reason")}
             onChange={(e) => form.setValue("reassignReason", e.target.value)}
-            required
+            required={confirmationModal?.membersStatus === "unavailable"}
           />
         </ConfirmationDialogContent>
       </Dialog>
diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index 06e4989743..4d8639b0e1 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -2708,7 +2708,9 @@
   "you_dont_have_access_to_reroute_this_booking": "You don't have access to reroute this booking",
   "form_response_not_found": "Form response not found",
   "confirm_reassign_unavailable": "Host unavailable",
+  "confirm_reassign_available": "Host available",
   "reassign_unavailable_team_member_description": "Are you sure you want to reassign this booking to an unavailable host?",
+  "reassign_available_team_member_description": "Are you sure you want to reassign this booking?",
   "yes_reassign": "Yes, reassign",
   "reassign_reason": "Reason for reassigning",
   "reassigned_by": "Reassigned by",
diff --git a/packages/features/ee/round-robin/roundRobinManualReassignment.ts b/packages/features/ee/round-robin/roundRobinManualReassignment.ts
index e46f957d2a..3184cc906f 100644
--- a/packages/features/ee/round-robin/roundRobinManualReassignment.ts
+++ b/packages/features/ee/round-robin/roundRobinManualReassignment.ts
@@ -42,11 +42,13 @@ export const roundRobinManualReassignment = async ({
   newUserId,
   orgId,
   reassignReason,
+  reassignedById,
 }: {
   bookingId: number;
   newUserId: number;
   orgId: number | null;
   reassignReason?: string;
+  reassignedById: number;
 }) => {
   const roundRobinReassignLogger = logger.getSubLogger({
     prefix: ["roundRobinManualReassign", `${bookingId}`],
@@ -164,6 +166,7 @@ export const roundRobinManualReassignment = async ({
         title: newBookingTitle,
         userPrimaryEmail: newUser.email,
         reassignReason,
+        reassignById: reassignedById,
       },
       select: bookingSelect,
     });
diff --git a/packages/lib/test/builder.ts b/packages/lib/test/builder.ts
index b040bc001e..cb4101d752 100644
--- a/packages/lib/test/builder.ts
+++ b/packages/lib/test/builder.ts
@@ -64,6 +64,7 @@ export const buildBooking = (
     fromReschedule: null,
     recurringEventId: null,
     smsReminderNumber: null,
+    reassignById: null,
     scheduledJobs: [],
     metadata: null,
     responses: null,
diff --git a/packages/prisma/migrations/20241031084229_add_reassign_by_column_to_booking/migration.sql b/packages/prisma/migrations/20241031084229_add_reassign_by_column_to_booking/migration.sql
new file mode 100644
index 0000000000..2041ecde88
--- /dev/null
+++ b/packages/prisma/migrations/20241031084229_add_reassign_by_column_to_booking/migration.sql
@@ -0,0 +1,5 @@
+-- AlterTable
+ALTER TABLE "Booking" ADD COLUMN     "reassignById" INTEGER;
+
+-- AddForeignKey
+ALTER TABLE "Booking" ADD CONSTRAINT "Booking_reassignById_fkey" FOREIGN KEY ("reassignById") REFERENCES "users"("id") ON DELETE SET NULL ON UPDATE CASCADE;
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index b22feb3781..af37489223 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -343,6 +343,7 @@ model User {
   NotificationsSubscriptions NotificationsSubscriptions[]
   referralLinkId             String?
   features                   UserFeatures[]
+  reassignedBookings         Booking[]                    @relation("reassignByUser")
 
   @@unique([email])
   @@unique([email, username])
@@ -608,6 +609,8 @@ model Booking {
   cancellationReason           String?
   rejectionReason              String?
   reassignReason               String?
+  reassignBy                   User?                          @relation("reassignByUser", fields: [reassignById], references: [id])
+  reassignById                 Int?
   dynamicEventSlugRef          String?
   dynamicGroupSlugRef          String?
   rescheduled                  Boolean?
diff --git a/packages/trpc/server/routers/viewer/teams/roundRobin/roundRobinManualReassign.handler.ts b/packages/trpc/server/routers/viewer/teams/roundRobin/roundRobinManualReassign.handler.ts
index f0d794bfe1..2629b65b80 100644
--- a/packages/trpc/server/routers/viewer/teams/roundRobin/roundRobinManualReassign.handler.ts
+++ b/packages/trpc/server/routers/viewer/teams/roundRobin/roundRobinManualReassign.handler.ts
@@ -28,6 +28,7 @@ export const roundRobinManualReassignHandler = async ({ ctx, input }: RoundRobin
     newUserId: teamMemberId,
     orgId: ctx.user.organizationId,
     reassignReason,
+    reassignedById: ctx.user.id,
   });
 
   return { success: true };
diff --git a/packages/ui/components/dialog/ConfirmationDialogContent.tsx b/packages/ui/components/dialog/ConfirmationDialogContent.tsx
index d196324dd1..5b011f1192 100644
--- a/packages/ui/components/dialog/ConfirmationDialogContent.tsx
+++ b/packages/ui/components/dialog/ConfirmationDialogContent.tsx
@@ -64,7 +64,7 @@ export const ConfirmationContent = (props: PropsWithChildren<ConfirmationDialogC
             )}
           </div>
         )}
-        <div>
+        <div className="w-full">
           <DialogPrimitive.Title className="font-cal text-emphasis mt-2 text-xl">
             {title}
           </DialogPrimitive.Title>