diff --git a/apps/api b/apps/api
index a1dcfa59..378cbf8f 160000
--- a/apps/api
+++ b/apps/api
@@ -1 +1 @@
-Subproject commit a1dcfa59bc43d3f71af62ae438f96a667e807913
+Subproject commit 378cbf8f3a67ea7877296f1da02edb2b6e3efbce
diff --git a/apps/web/components/booking/BookingListItem.tsx b/apps/web/components/booking/BookingListItem.tsx
index 8036bb4b..62c370e1 100644
--- a/apps/web/components/booking/BookingListItem.tsx
+++ b/apps/web/components/booking/BookingListItem.tsx
@@ -1,18 +1,21 @@
 import { BanIcon, CheckIcon, ClockIcon, XIcon } from "@heroicons/react/outline";
+import { PaperAirplaneIcon } from "@heroicons/react/outline";
 import { BookingStatus } from "@prisma/client";
 import dayjs from "dayjs";
 import { useState } from "react";
 import { useMutation } from "react-query";
 
+import classNames from "@calcom/lib/classNames";
+import { useLocale } from "@calcom/lib/hooks/useLocale";
 import Button from "@calcom/ui/Button";
 import { Dialog, DialogClose, DialogContent, DialogFooter, DialogHeader } from "@calcom/ui/Dialog";
 import { TextArea } from "@calcom/ui/form/fields";
 
 import { HttpError } from "@lib/core/http/error";
-import { useLocale } from "@lib/hooks/useLocale";
 import { inferQueryOutput, trpc } from "@lib/trpc";
 
 import { useMeQuery } from "@components/Shell";
+import { RescheduleDialog } from "@components/dialog/RescheduleDialog";
 import TableActions, { ActionType } from "@components/ui/TableActions";
 
 type BookingItem = inferQueryOutput<"viewer.bookings">["bookings"][number];
@@ -80,15 +83,42 @@ function BookingListItem(booking: BookingItem) {
     {
       id: "reschedule",
       label: t("reschedule"),
-      href: `/reschedule/${booking.uid}`,
       icon: ClockIcon,
+      actions: [
+        {
+          id: "edit",
+          label: t("reschedule_booking"),
+          href: `/reschedule/${booking.uid}`,
+        },
+        {
+          id: "reschedule_request",
+          label: t("send_reschedule_request"),
+          onClick: () => setIsOpenRescheduleDialog(true),
+        },
+      ],
     },
   ];
 
-  const startTime = dayjs(booking.startTime).format(isUpcoming ? "ddd, D MMM" : "D MMMM YYYY");
+  const RequestSentMessage = () => {
+    return (
+      <div className="ml-1 mr-8 flex text-gray-500" data-testid="request_reschedule_sent">
+        <PaperAirplaneIcon className="-mt-[1px] w-4 rotate-45" />
+        <p className="ml-2 ">{t("reschedule_request_sent")}</p>
+      </div>
+    );
+  };
 
+  const startTime = dayjs(booking.startTime).format(isUpcoming ? "ddd, D MMM" : "D MMMM YYYY");
+  const [isOpenRescheduleDialog, setIsOpenRescheduleDialog] = useState(false);
   return (
     <>
+      <RescheduleDialog
+        isOpenDialog={isOpenRescheduleDialog}
+        setIsOpenDialog={setIsOpenRescheduleDialog}
+        bookingUId={booking.uid}
+      />
+
+      {/* NOTE: Should refactor this dialog component as is being rendered multiple times */}
       <Dialog open={rejectionDialogIsOpen} onOpenChange={setRejectionDialogIsOpen}>
         <DialogContent>
           <DialogHeader title={t("rejection_reason_title")} />
@@ -146,7 +176,10 @@ function BookingListItem(booking: BookingItem) {
           </div>
           <div
             title={booking.title}
-            className="max-w-56 truncate text-sm font-medium leading-6 text-neutral-900 md:max-w-max">
+            className={classNames(
+              "max-w-56 truncate text-sm font-medium leading-6 text-neutral-900 md:max-w-max",
+              isCancelled ? "line-through" : ""
+            )}>
             {booking.eventType?.team && <strong>{booking.eventType.team.name}: </strong>}
             {booking.title}
             {!!booking?.eventType?.price && !booking.paid && (
@@ -161,11 +194,17 @@ function BookingListItem(booking: BookingItem) {
               &quot;{booking.description}&quot;
             </div>
           )}
+
           {booking.attendees.length !== 0 && (
             <div className="text-sm text-gray-900 hover:text-blue-500">
               <a href={"mailto:" + booking.attendees[0].email}>{booking.attendees[0].email}</a>
             </div>
           )}
+          {isCancelled && booking.rescheduled && (
+            <div className="mt-2 inline-block text-left text-sm md:hidden">
+              <RequestSentMessage />
+            </div>
+          )}
         </td>
 
         <td className="whitespace-nowrap py-4 text-right text-sm font-medium ltr:pr-4 rtl:pl-4">
@@ -180,6 +219,11 @@ function BookingListItem(booking: BookingItem) {
               )}
             </>
           ) : null}
+          {isCancelled && booking.rescheduled && (
+            <div className="hidden h-full items-center md:flex">
+              <RequestSentMessage />
+            </div>
+          )}
         </td>
       </tr>
     </>
diff --git a/apps/web/components/booking/pages/AvailabilityPage.tsx b/apps/web/components/booking/pages/AvailabilityPage.tsx
index cd2c2813..c561bad5 100644
--- a/apps/web/components/booking/pages/AvailabilityPage.tsx
+++ b/apps/web/components/booking/pages/AvailabilityPage.tsx
@@ -1,11 +1,13 @@
 // Get router variables
 import {
   ArrowLeftIcon,
+  CalendarIcon,
   ChevronDownIcon,
   ChevronUpIcon,
   ClockIcon,
   CreditCardIcon,
   GlobeIcon,
+  InformationCircleIcon,
 } from "@heroicons/react/solid";
 import * as Collapsible from "@radix-ui/react-collapsible";
 import { useContracts } from "contexts/contractsContext";
@@ -18,14 +20,15 @@ import { FormattedNumber, IntlProvider } from "react-intl";
 
 import { useEmbedStyles, useIsEmbed, useIsBackgroundTransparent, sdkActionManager } from "@calcom/embed-core";
 import classNames from "@calcom/lib/classNames";
+import { useLocale } from "@calcom/lib/hooks/useLocale";
 
 import { asStringOrNull } from "@lib/asStringOrNull";
 import { timeZone } from "@lib/clock";
 import { BASE_URL } from "@lib/config/constants";
 import { useExposePlanGlobally } from "@lib/hooks/useExposePlanGlobally";
-import { useLocale } from "@lib/hooks/useLocale";
 import useTheme from "@lib/hooks/useTheme";
 import { isBrandingHidden } from "@lib/isBrandingHidden";
+import { parseDate } from "@lib/parseDate";
 import { collectPageParameters, telemetryEventTypes, useTelemetry } from "@lib/telemetry";
 import { detectBrowserTimeFormat } from "@lib/timeFormat";
 
@@ -45,12 +48,12 @@ dayjs.extend(customParseFormat);
 
 type Props = AvailabilityTeamPageProps | AvailabilityPageProps;
 
-const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage }: Props) => {
+const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage, booking }: Props) => {
   const router = useRouter();
   const isEmbed = useIsEmbed();
   const { rescheduleUid } = router.query;
   const { isReady, Theme } = useTheme(profile.theme);
-  const { t } = useLocale();
+  const { t, i18n } = useLocale();
   const { contracts } = useContracts();
   const availabilityDatePickerEmbedStyles = useEmbedStyles("availabilityDatePicker");
   let isBackgroundTransparent = useIsBackgroundTransparent();
@@ -179,15 +182,21 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
                   />
                   <div className="mt-4 sm:-mt-2">
                     <p className="text-sm font-medium text-black dark:text-white">{profile.name}</p>
-                    <div className="text-bookingmedian flex gap-2 text-xs font-medium dark:text-gray-100">
+                    <div className="mt-2 flex gap-2 text-xl font-medium dark:text-gray-100">
                       {eventType.title}
+                      {eventType?.description && (
+                        <p className="mb-2 text-gray-600 dark:text-white">
+                          <InformationCircleIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4" />
+                          {eventType.description}
+                        </p>
+                      )}
                       <div>
-                        <ClockIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                        <ClockIcon className="mr-[10px] -mt-1 inline-block h-4 w-4" />
                         {eventType.length} {t("minutes")}
                       </div>
                       {eventType.price > 0 && (
-                        <div>
-                          <CreditCardIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                        <div className="text-gray-600 dark:text-white">
+                          <CreditCardIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 dark:text-gray-400" />
                           <IntlProvider locale="en">
                             <FormattedNumber
                               value={eventType.price / 100.0}
@@ -200,7 +209,6 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
                     </div>
                   </div>
                 </div>
-                <p className="mt-3 text-gray-600 dark:text-gray-200">{eventType.description}</p>
               </div>
 
               <div className="px-4 sm:flex sm:p-4 sm:py-5">
@@ -226,17 +234,23 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
                     size={10}
                     truncateAfter={3}
                   />
-                  <h2 className="dark:text-bookinglight mt-3 font-medium text-gray-500">{profile.name}</h2>
-                  <h1 className="font-cal text-bookingdark mb-4 text-3xl font-semibold dark:text-white">
+                  <h2 className="mt-3 font-medium text-gray-500 dark:text-gray-300">{profile.name}</h2>
+                  <h1 className="font-cal mb-4 text-xl font-semibold text-gray-900 dark:text-white">
                     {eventType.title}
                   </h1>
-                  <p className="text-bookinglight mb-1 -ml-2 px-2 py-1">
-                    <ClockIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                  {eventType?.description && (
+                    <p className="mb-2 text-gray-600 dark:text-white">
+                      <InformationCircleIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 text-gray-400" />
+                      {eventType.description}
+                    </p>
+                  )}
+                  <p className="mb-1 -ml-2 px-2 py-1 text-gray-600 dark:text-white">
+                    <ClockIcon className="mr-[10px] -mt-1 ml-[2px] inline-block h-4 w-4 text-gray-400" />
                     {eventType.length} {t("minutes")}
                   </p>
                   {eventType.price > 0 && (
-                    <p className="text-bookinglight mb-1 -ml-2 px-2 py-1">
-                      <CreditCardIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                    <p className="mb-1 -ml-2 px-2 py-1 text-gray-600 dark:text-white">
+                      <CreditCardIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 text-gray-400" />
                       <IntlProvider locale="en">
                         <FormattedNumber
                           value={eventType.price / 100.0}
@@ -248,8 +262,6 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
                   )}
 
                   <TimezoneDropdown />
-
-                  <p className="mt-3 mb-8 text-gray-600 dark:text-gray-200">{eventType.description}</p>
                   {previousPage === `${BASE_URL}/${profile.slug}` && (
                     <div className="flex h-full flex-col justify-end">
                       <ArrowLeftIcon
@@ -259,6 +271,17 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
                       <p className="sr-only">Go Back</p>
                     </div>
                   )}
+                  {booking?.startTime && rescheduleUid && (
+                    <div>
+                      <p className="mt-8 mb-2 text-gray-600 dark:text-white" data-testid="former_time_p">
+                        {t("former_time")}
+                      </p>
+                      <p className="text-gray-500 line-through dark:text-white">
+                        <CalendarIcon className="mr-[10px] -mt-1 inline-block h-4 w-4 text-gray-400" />
+                        {typeof booking.startTime === "string" && parseDate(dayjs(booking.startTime), i18n)}
+                      </p>
+                    </div>
+                  )}
                 </div>
                 <DatePicker
                   date={selectedDate}
@@ -305,8 +328,8 @@ const AvailabilityPage = ({ profile, plan, eventType, workingHours, previousPage
   function TimezoneDropdown() {
     return (
       <Collapsible.Root open={isTimeOptionsOpen} onOpenChange={setIsTimeOptionsOpen}>
-        <Collapsible.Trigger className="min-w-32 text-bookinglight mb-1 -ml-2 px-2 py-1 text-left">
-          <GlobeIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+        <Collapsible.Trigger className="min-w-32 mb-1 -ml-2 px-2 py-1 text-left text-gray-600 dark:text-white">
+          <GlobeIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 text-gray-400" />
           {timeZone()}
           {isTimeOptionsOpen ? (
             <ChevronUpIcon className="ml-1 -mt-1 inline-block h-4 w-4" />
diff --git a/apps/web/components/booking/pages/BookingPage.tsx b/apps/web/components/booking/pages/BookingPage.tsx
index dd36b04f..fe317dd0 100644
--- a/apps/web/components/booking/pages/BookingPage.tsx
+++ b/apps/web/components/booking/pages/BookingPage.tsx
@@ -1,4 +1,10 @@
-import { CalendarIcon, ClockIcon, CreditCardIcon, ExclamationIcon } from "@heroicons/react/solid";
+import {
+  CalendarIcon,
+  ClockIcon,
+  CreditCardIcon,
+  ExclamationIcon,
+  InformationCircleIcon,
+} from "@heroicons/react/solid";
 import { EventTypeCustomInputType } from "@prisma/client";
 import { useContracts } from "contexts/contractsContext";
 import dayjs from "dayjs";
@@ -12,7 +18,7 @@ import { FormattedNumber, IntlProvider } from "react-intl";
 import { ReactMultiEmail } from "react-multi-email";
 import { useMutation } from "react-query";
 
-import { useIsEmbed, useEmbedStyles, useIsBackgroundTransparent } from "@calcom/embed-core";
+import { useIsEmbed, useIsBackgroundTransparent } from "@calcom/embed-core";
 import classNames from "@calcom/lib/classNames";
 import { useLocale } from "@calcom/lib/hooks/useLocale";
 import { HttpError } from "@calcom/lib/http-error";
@@ -26,10 +32,9 @@ import { ensureArray } from "@lib/ensureArray";
 import useTheme from "@lib/hooks/useTheme";
 import { LocationType } from "@lib/location";
 import createBooking from "@lib/mutations/bookings/create-booking";
-import { parseZone } from "@lib/parseZone";
+import { parseDate } from "@lib/parseDate";
 import slugify from "@lib/slugify";
 import { collectPageParameters, telemetryEventTypes, useTelemetry } from "@lib/telemetry";
-import { detectBrowserTimeFormat } from "@lib/timeFormat";
 
 import CustomBranding from "@components/CustomBranding";
 import AvatarGroup from "@components/ui/AvatarGroup";
@@ -147,6 +152,10 @@ const BookingPage = ({
 
   const locationInfo = (type: LocationType) => locations.find((location) => location.type === type);
   const loggedInIsOwner = eventType?.users[0]?.name === session?.user?.name;
+  const guestListEmails = !isDynamicGroupBooking
+    ? booking?.attendees.slice(1).map((attendee) => attendee.email)
+    : [];
+
   const defaultValues = () => {
     if (!rescheduleUid) {
       return {
@@ -173,7 +182,8 @@ const BookingPage = ({
     return {
       name: primaryAttendee.name || "",
       email: primaryAttendee.email || "",
-      guests: !isDynamicGroupBooking ? booking.attendees.slice(1).map((attendee) => attendee.email) : [],
+      guests: guestListEmails,
+      notes: booking.description || "",
     };
   };
 
@@ -212,14 +222,6 @@ const BookingPage = ({
     }
   };
 
-  const parseDate = (date: string | null) => {
-    if (!date) return "No date";
-    const parsedZone = parseZone(date);
-    if (!parsedZone?.isValid()) return "Invalid date";
-    const formattedTime = parsedZone?.format(detectBrowserTimeFormat);
-    return formattedTime + ", " + dayjs(date).toDate().toLocaleString(i18n.language, { dateStyle: "full" });
-  };
-
   const bookEvent = (booking: BookingFormValues) => {
     telemetry.withJitsu((jitsu) =>
       jitsu.track(
@@ -273,6 +275,8 @@ const BookingPage = ({
     });
   };
 
+  const disableInput = !!rescheduleUid;
+
   return (
     <div>
       <Theme />
@@ -322,16 +326,22 @@ const BookingPage = ({
                 <h2 className="font-cal text-bookinglight mt-2 font-medium dark:text-gray-300">
                   {profile.name}
                 </h2>
-                <h1 className="text-bookingdark mb-4 text-3xl font-semibold dark:text-white">
+                <h1 className="text-bookingdark mb-4 text-xl font-semibold dark:text-white">
                   {eventType.title}
                 </h1>
-                <p className="text-bookinglight mb-2">
-                  <ClockIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                {eventType?.description && (
+                  <p className="text-bookinglight mb-2 dark:text-white">
+                    <InformationCircleIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 text-gray-400" />
+                    {eventType.description}
+                  </p>
+                )}
+                <p className="text-bookinglight mb-2 dark:text-white">
+                  <ClockIcon className="mr-[10px] -mt-1 ml-[2px] inline-block h-4 w-4 text-gray-400" />
                   {eventType.length} {t("minutes")}
                 </p>
                 {eventType.price > 0 && (
-                  <p className="text-bookinglight mb-1 -ml-2 px-2 py-1">
-                    <CreditCardIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
+                  <p className="text-bookinglight mb-1 -ml-2 px-2 py-1 dark:text-white">
+                    <CreditCardIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4" />
                     <IntlProvider locale="en">
                       <FormattedNumber
                         value={eventType.price / 100.0}
@@ -342,15 +352,25 @@ const BookingPage = ({
                   </p>
                 )}
                 <p className="text-bookinghighlight mb-4">
-                  <CalendarIcon className="mr-1 -mt-1 inline-block h-4 w-4" />
-                  {parseDate(date)}
+                  <CalendarIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4" />
+                  {parseDate(date, i18n)}
                 </p>
                 {eventTypeDetail.isWeb3Active && eventType.metadata.smartContractAddress && (
                   <p className="text-bookinglight mb-1 -ml-2 px-2 py-1">
                     {t("requires_ownership_of_a_token") + " " + eventType.metadata.smartContractAddress}
                   </p>
                 )}
-                <p className="mb-8 text-gray-600 dark:text-white">{eventType.description}</p>
+                {booking?.startTime && rescheduleUid && (
+                  <div>
+                    <p className="mt-8 mb-2 text-gray-600 dark:text-white" data-testid="former_time_p">
+                      {t("former_time")}
+                    </p>
+                    <p className="text-gray-500 line-through dark:text-white">
+                      <CalendarIcon className="mr-[10px] ml-[2px] -mt-1 inline-block h-4 w-4 text-gray-400" />
+                      {typeof booking.startTime === "string" && parseDate(dayjs(booking.startTime), i18n)}
+                    </p>
+                  </div>
+                )}
               </div>
               <div className="sm:w-1/2 sm:pl-8 sm:pr-4">
                 <Form form={bookingForm} handleSubmit={bookEvent}>
@@ -365,8 +385,12 @@ const BookingPage = ({
                         name="name"
                         id="name"
                         required
-                        className="focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm"
+                        className={classNames(
+                          "focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm",
+                          disableInput ? "bg-gray-200 dark:text-gray-500" : ""
+                        )}
                         placeholder={t("example_name")}
+                        disabled={disableInput}
                       />
                     </div>
                   </div>
@@ -380,9 +404,13 @@ const BookingPage = ({
                       <EmailInput
                         {...bookingForm.register("email")}
                         required
-                        className="focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm"
+                        className={classNames(
+                          "focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm",
+                          disableInput ? "bg-gray-200 dark:text-gray-500" : ""
+                        )}
                         placeholder="you@example.com"
                         type="search" // Disables annoying 1password intrusive popup (non-optimal, I know I know...)
+                        disabled={disableInput}
                       />
                     </div>
                   </div>
@@ -399,6 +427,7 @@ const BookingPage = ({
                             {...bookingForm.register("locationType", { required: true })}
                             value={location.type}
                             defaultChecked={selectedLocation === location.type}
+                            disabled={disableInput}
                           />
                           <span className="text-sm ltr:ml-2 rtl:mr-2 dark:text-gray-500">
                             {locationLabels[location.type]}
@@ -421,6 +450,7 @@ const BookingPage = ({
                           placeholder={t("enter_phone_number")}
                           id="phone"
                           required
+                          disabled={disableInput}
                         />
                       </div>
                     </div>
@@ -443,8 +473,12 @@ const BookingPage = ({
                             })}
                             id={"custom_" + input.id}
                             rows={3}
-                            className="focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm"
+                            className={classNames(
+                              "focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm",
+                              disableInput ? "bg-gray-200 dark:text-gray-500" : ""
+                            )}
                             placeholder={input.placeholder}
+                            disabled={disableInput}
                           />
                         )}
                         {input.type === EventTypeCustomInputType.TEXT && (
@@ -456,6 +490,7 @@ const BookingPage = ({
                             id={"custom_" + input.id}
                             className="focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm"
                             placeholder={input.placeholder}
+                            disabled={disableInput}
                           />
                         )}
                         {input.type === EventTypeCustomInputType.NUMBER && (
@@ -507,32 +542,49 @@ const BookingPage = ({
                             className="mb-1 block text-sm font-medium text-gray-700 dark:text-white">
                             {t("guests")}
                           </label>
-                          <Controller
-                            control={bookingForm.control}
-                            name="guests"
-                            render={({ field: { onChange, value } }) => (
-                              <ReactMultiEmail
-                                className="relative"
-                                placeholder="guest@example.com"
-                                emails={value}
-                                onChange={onChange}
-                                getLabel={(
-                                  email: string,
-                                  index: number,
-                                  removeEmail: (index: number) => void
-                                ) => {
-                                  return (
-                                    <div data-tag key={index}>
-                                      {email}
-                                      <span data-tag-handle onClick={() => removeEmail(index)}>
-                                        ×
-                                      </span>
-                                    </div>
-                                  );
-                                }}
-                              />
-                            )}
-                          />
+                          {!disableInput && (
+                            <Controller
+                              control={bookingForm.control}
+                              name="guests"
+                              render={({ field: { onChange, value } }) => (
+                                <ReactMultiEmail
+                                  className="relative"
+                                  placeholder="guest@example.com"
+                                  emails={value}
+                                  onChange={onChange}
+                                  getLabel={(
+                                    email: string,
+                                    index: number,
+                                    removeEmail: (index: number) => void
+                                  ) => {
+                                    return (
+                                      <div data-tag key={index} className="cursor-pointer">
+                                        {email}
+                                        {!disableInput && (
+                                          <span data-tag-handle onClick={() => removeEmail(index)}>
+                                            ×
+                                          </span>
+                                        )}
+                                      </div>
+                                    );
+                                  }}
+                                />
+                              )}
+                            />
+                          )}
+                          {/* Custom code when guest emails should not be editable */}
+                          {disableInput && guestListEmails && guestListEmails.length > 0 && (
+                            <div data-tag className="react-multi-email">
+                              {/* // @TODO: user owners are appearing as guest here when should be only user input */}
+                              {guestListEmails.map((email, index) => {
+                                return (
+                                  <div key={index} className="cursor-pointer">
+                                    <span data-tag>{email}</span>
+                                  </div>
+                                );
+                              })}
+                            </div>
+                          )}
                         </div>
                       )}
                     </div>
@@ -546,9 +598,14 @@ const BookingPage = ({
                     <textarea
                       {...bookingForm.register("notes")}
                       id="notes"
+                      name="notes"
                       rows={3}
-                      className="focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm"
+                      className={classNames(
+                        "focus:border-brand block w-full rounded-sm border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white dark:selection:bg-green-500 sm:text-sm",
+                        disableInput ? "bg-gray-200 dark:text-gray-500" : ""
+                      )}
                       placeholder={t("share_additional_notes")}
+                      disabled={disableInput}
                     />
                   </div>
                   <div className="flex items-start space-x-2 rtl:space-x-reverse">
diff --git a/apps/web/components/dialog/RescheduleDialog.tsx b/apps/web/components/dialog/RescheduleDialog.tsx
new file mode 100644
index 00000000..539b667b
--- /dev/null
+++ b/apps/web/components/dialog/RescheduleDialog.tsx
@@ -0,0 +1,102 @@
+import { ClockIcon, XIcon } from "@heroicons/react/outline";
+import { RescheduleResponse } from "pages/api/book/request-reschedule";
+import React, { useState, Dispatch, SetStateAction } from "react";
+import { useMutation } from "react-query";
+
+import { useLocale } from "@calcom/lib/hooks/useLocale";
+import showToast from "@calcom/lib/notification";
+import Button from "@calcom/ui/Button";
+import { Dialog, DialogClose, DialogContent, DialogFooter, DialogHeader } from "@calcom/ui/Dialog";
+import { TextArea } from "@calcom/ui/form/fields";
+
+import * as fetchWrapper from "@lib/core/http/fetch-wrapper";
+import { trpc } from "@lib/trpc";
+
+interface IRescheduleDialog {
+  isOpenDialog: boolean;
+  setIsOpenDialog: Dispatch<SetStateAction<boolean>>;
+  bookingUId: string;
+}
+
+export const RescheduleDialog = (props: IRescheduleDialog) => {
+  const { t } = useLocale();
+  const utils = trpc.useContext();
+  const { isOpenDialog, setIsOpenDialog, bookingUId: bookingId } = props;
+  const [rescheduleReason, setRescheduleReason] = useState("");
+  const [isLoading, setIsLoading] = useState(false);
+  const rescheduleApi = useMutation(
+    async () => {
+      setIsLoading(true);
+      try {
+        const result = await fetchWrapper.post<
+          { bookingId: string; rescheduleReason: string },
+          RescheduleResponse
+        >("/api/book/request-reschedule", {
+          bookingId,
+          rescheduleReason,
+        });
+
+        if (result) {
+          showToast(t("reschedule_request_sent"), "success");
+          setIsOpenDialog(false);
+        }
+      } catch (error) {
+        showToast(t("unexpected_error_try_again"), "error");
+        // @TODO: notify sentry
+      }
+      setIsLoading(false);
+    },
+    {
+      async onSettled() {
+        await utils.invalidateQueries(["viewer.bookings"]);
+      },
+    }
+  );
+
+  return (
+    <Dialog open={isOpenDialog} onOpenChange={setIsOpenDialog}>
+      <DialogContent>
+        <DialogClose asChild>
+          <div className="fixed top-1 right-1 flex h-8 w-8 justify-center rounded-full hover:bg-gray-200">
+            <XIcon className="w-4" />
+          </div>
+        </DialogClose>
+        <div style={{ display: "flex", flexDirection: "row" }}>
+          <div className="flex h-10 w-10 flex-shrink-0 justify-center rounded-full bg-[#FAFAFA]">
+            <ClockIcon className="m-auto h-6 w-6"></ClockIcon>
+          </div>
+          <div className="px-4 pt-1">
+            <DialogHeader title={t("send_reschedule_request")} />
+
+            <p className="-mt-8 text-sm text-gray-500">{t("reschedule_modal_description")}</p>
+            <p className="mt-6 mb-2 text-sm font-bold text-black">
+              {t("reason_for_reschedule_request")}
+              <span className="font-normal text-gray-500"> (Optional)</span>
+            </p>
+            <TextArea
+              data-testid="reschedule_reason"
+              name={t("reschedule_reason")}
+              value={rescheduleReason}
+              onChange={(e) => setRescheduleReason(e.target.value)}
+              className="mb-5 sm:mb-6"
+            />
+
+            <DialogFooter>
+              <DialogClose>
+                <Button color="secondary">{t("cancel")}</Button>
+              </DialogClose>
+              <Button
+                data-testid="send_request"
+                disabled={isLoading}
+                onClick={() => {
+                  rescheduleApi.mutate();
+                }}>
+                {t("send_reschedule_request")}
+              </Button>
+            </DialogFooter>
+          </div>
+        </div>
+      </DialogContent>
+    </Dialog>
+  );
+};
diff --git a/apps/web/components/ui/TableActions.tsx b/apps/web/components/ui/TableActions.tsx
index 94ebe93d..1716bd1d 100644
--- a/apps/web/components/ui/TableActions.tsx
+++ b/apps/web/components/ui/TableActions.tsx
@@ -1,7 +1,6 @@
-import { DotsHorizontalIcon } from "@heroicons/react/solid";
+import { ChevronDownIcon, DotsHorizontalIcon } from "@heroicons/react/solid";
 import React, { FC } from "react";
 
-import { useLocale } from "@calcom/lib/hooks/useLocale";
 import Button from "@calcom/ui/Button";
 import Dropdown, { DropdownMenuTrigger, DropdownMenuContent, DropdownMenuItem } from "@calcom/ui/Dropdown";
 
@@ -9,56 +8,76 @@ import { SVGComponent } from "@lib/types/SVGComponent";
 
 export type ActionType = {
   id: string;
-  icon: SVGComponent;
+  icon?: SVGComponent;
   label: string;
   disabled?: boolean;
   color?: "primary" | "secondary";
-} & ({ href?: never; onClick: () => any } | { href: string; onClick?: never });
+} & ({ href?: never; onClick: () => any } | { href?: string; onClick?: never }) & {
+    actions?: ActionType[];
+  };
 
 interface Props {
   actions: ActionType[];
 }
 
+const DropdownActions = ({ actions, actionTrigger }: { actions: ActionType[]; actionTrigger?: any }) => {
+  return (
+    <Dropdown>
+      {!actionTrigger ? (
+        <DropdownMenuTrigger className="h-[38px] w-[38px] cursor-pointer rounded-sm border border-transparent text-neutral-500 hover:border-gray-300 hover:text-neutral-900">
+          <DotsHorizontalIcon className="h-5 w-5 group-hover:text-gray-800" />
+        </DropdownMenuTrigger>
+      ) : (
+        <DropdownMenuTrigger asChild>{actionTrigger}</DropdownMenuTrigger>
+      )}
+      <DropdownMenuContent portalled>
+        {actions.map((action) => (
+          <DropdownMenuItem key={action.id} className="focus-visible:outline-none">
+            <Button
+              type="button"
+              size="sm"
+              color="minimal"
+              className="w-full rounded-none font-normal"
+              href={action.href}
+              StartIcon={action.icon}
+              onClick={action.onClick}
+              data-testid={action.id}>
+              {action.label}
+            </Button>
+          </DropdownMenuItem>
+        ))}
+      </DropdownMenuContent>
+    </Dropdown>
+  );
+};
+
 const TableActions: FC<Props> = ({ actions }) => {
-  const { t } = useLocale();
   return (
     <>
       <div className="hidden space-x-2 rtl:space-x-reverse lg:block">
-        {actions.map((action) => (
-          <Button
-            key={action.id}
-            data-testid={action.id}
-            href={action.href}
-            onClick={action.onClick}
-            StartIcon={action.icon}
-            disabled={action.disabled}
-            color={action.color || "secondary"}>
-            {action.label}
-          </Button>
-        ))}
+        {actions.map((action) => {
+          const button = (
+            <Button
+              key={action.id}
+              data-testid={action.id}
+              href={action.href}
+              onClick={action.onClick}
+              StartIcon={action.icon}
+              {...(action?.actions ? { EndIcon: ChevronDownIcon } : null)}
+              disabled={action.disabled}
+              color={action.color || "secondary"}>
+              {action.label}
+            </Button>
+          );
+          if (!action.actions) {
+            return button;
+          }
+
+          return <DropdownActions key={action.id} actions={action.actions} actionTrigger={button} />;
+        })}
       </div>
       <div className="inline-block text-left lg:hidden">
-        <Dropdown>
-          <DropdownMenuTrigger className="h-[38px] w-[38px] cursor-pointer rounded-sm border border-transparent text-neutral-500 hover:border-gray-300 hover:text-neutral-900">
-            <DotsHorizontalIcon className="h-5 w-5 group-hover:text-gray-800" />
-          </DropdownMenuTrigger>
-          <DropdownMenuContent portalled>
-            {actions.map((action) => (
-              <DropdownMenuItem key={action.id}>
-                <Button
-                  type="button"
-                  size="lg"
-                  color="minimal"
-                  className="w-full rounded-none font-normal"
-                  href={action.href}
-                  StartIcon={action.icon}
-                  onClick={action.onClick}>
-                  {action.label}
-                </Button>
-              </DropdownMenuItem>
-            ))}
-          </DropdownMenuContent>
-        </Dropdown>
+        <DropdownActions actions={actions} />
       </div>
     </>
   );
diff --git a/apps/web/components/ui/form/PhoneInput.tsx b/apps/web/components/ui/form/PhoneInput.tsx
index 2689273e..5455c21b 100644
--- a/apps/web/components/ui/form/PhoneInput.tsx
+++ b/apps/web/components/ui/form/PhoneInput.tsx
@@ -20,7 +20,8 @@ function PhoneInput<FormValues>({ control, name, ...rest }: PhoneInputProps<Form
       name={name}
       control={control}
       className={classNames(
-        "border-1 focus-within:border-brand block w-full rounded-sm border border-gray-300 py-px px-3 shadow-sm ring-black focus-within:ring-1 dark:border-black dark:bg-black dark:text-white"
+        "border-1 focus-within:border-brand block w-full rounded-sm border border-gray-300 py-px px-3 shadow-sm ring-black focus-within:ring-1 dark:border-black dark:bg-black dark:text-white",
+        rest.disabled ? "bg-gray-200 dark:text-gray-500" : ""
       )}
     />
   );
diff --git a/apps/web/ee/components/stripe/PaymentPage.tsx b/apps/web/ee/components/stripe/PaymentPage.tsx
index e4e0c897..bed4afd9 100644
--- a/apps/web/ee/components/stripe/PaymentPage.tsx
+++ b/apps/web/ee/components/stripe/PaymentPage.tsx
@@ -14,6 +14,7 @@ import { PaymentPageProps } from "@ee/pages/payment/[uid]";
 
 import { useLocale } from "@lib/hooks/useLocale";
 import useTheme from "@lib/hooks/useTheme";
+import { LocationOptionsToString } from "@lib/locationOptions";
 import { isBrowserLocale24h } from "@lib/timeFormat";
 
 dayjs.extend(utc);
@@ -58,6 +59,7 @@ const PaymentPage: FC<PaymentPageProps> = (props) => {
                   <div className="mx-auto flex h-12 w-12 items-center justify-center rounded-full bg-green-100">
                     <CreditCardIcon className="h-8 w-8 text-green-600" />
                   </div>
+
                   <div className="mt-3 text-center sm:mt-5">
                     <h3
                       className="text-2xl font-semibold leading-6 text-neutral-900 dark:text-white"
@@ -84,7 +86,9 @@ const PaymentPage: FC<PaymentPageProps> = (props) => {
                       {props.booking.location && (
                         <>
                           <div className="font-medium">{t("where")}</div>
-                          <div className="col-span-2 mb-6">{props.booking.location}</div>
+                          <div className="col-span-2 mb-6">
+                            {LocationOptionsToString(props.booking.location, t)}
+                          </div>
                         </>
                       )}
                       <div className="font-medium">{t("price")}</div>
diff --git a/apps/web/lib/attendeeToPersonConversionType.ts b/apps/web/lib/attendeeToPersonConversionType.ts
new file mode 100644
index 00000000..08be1a25
--- /dev/null
+++ b/apps/web/lib/attendeeToPersonConversionType.ts
@@ -0,0 +1,16 @@
+import { TFunction } from "next-i18next";
+
+import { Attendee } from "@calcom/prisma/client";
+import { Person } from "@calcom/types/Calendar";
+
+export const attendeeToPersonConversionType = (attendees: Attendee[], t: TFunction): Person[] => {
+  return attendees.map((attendee) => {
+    return {
+      name: attendee.name,
+      email: attendee.email,
+      timeZone: attendee.timeZone,
+      locale: attendee.locale || "en",
+      language: { translate: t, locale: attendee.locale || "en" },
+    };
+  });
+};
diff --git a/apps/web/lib/emails/email-manager.ts b/apps/web/lib/emails/email-manager.ts
index 910b2bc3..ae681f70 100644
--- a/apps/web/lib/emails/email-manager.ts
+++ b/apps/web/lib/emails/email-manager.ts
@@ -4,6 +4,7 @@ import AttendeeAwaitingPaymentEmail from "@lib/emails/templates/attendee-awaitin
 import AttendeeCancelledEmail from "@lib/emails/templates/attendee-cancelled-email";
 import AttendeeDeclinedEmail from "@lib/emails/templates/attendee-declined-email";
 import AttendeeRequestEmail from "@lib/emails/templates/attendee-request-email";
+import AttendeeRequestRescheduledEmail from "@lib/emails/templates/attendee-request-reschedule-email";
 import AttendeeRescheduledEmail from "@lib/emails/templates/attendee-rescheduled-email";
 import AttendeeScheduledEmail from "@lib/emails/templates/attendee-scheduled-email";
 import ForgotPasswordEmail, { PasswordReset } from "@lib/emails/templates/forgot-password-email";
@@ -11,6 +12,7 @@ import OrganizerCancelledEmail from "@lib/emails/templates/organizer-cancelled-e
 import OrganizerPaymentRefundFailedEmail from "@lib/emails/templates/organizer-payment-refund-failed-email";
 import OrganizerRequestEmail from "@lib/emails/templates/organizer-request-email";
 import OrganizerRequestReminderEmail from "@lib/emails/templates/organizer-request-reminder-email";
+import OrganizerRequestRescheduleEmail from "@lib/emails/templates/organizer-request-reschedule-email";
 import OrganizerRescheduledEmail from "@lib/emails/templates/organizer-rescheduled-email";
 import OrganizerScheduledEmail from "@lib/emails/templates/organizer-scheduled-email";
 import TeamInviteEmail, { TeamInvite } from "@lib/emails/templates/team-invite-email";
@@ -208,3 +210,34 @@ export const sendTeamInviteEmail = async (teamInviteEvent: TeamInvite) => {
     }
   });
 };
+
+export const sendRequestRescheduleEmail = async (
+  calEvent: CalendarEvent,
+  metadata: { rescheduleLink: string }
+) => {
+  const emailsToSend: Promise<unknown>[] = [];
+
+  emailsToSend.push(
+    new Promise((resolve, reject) => {
+      try {
+        const requestRescheduleEmail = new AttendeeRequestRescheduledEmail(calEvent, metadata);
+        resolve(requestRescheduleEmail.sendEmail());
+      } catch (e) {
+        reject(console.error("AttendeeRequestRescheduledEmail.sendEmail failed", e));
+      }
+    })
+  );
+
+  emailsToSend.push(
+    new Promise((resolve, reject) => {
+      try {
+        const requestRescheduleEmail = new OrganizerRequestRescheduleEmail(calEvent, metadata);
+        resolve(requestRescheduleEmail.sendEmail());
+      } catch (e) {
+        reject(console.error("OrganizerRequestRescheduledEmail.sendEmail failed", e));
+      }
+    })
+  );
+
+  await Promise.all(emailsToSend);
+};
diff --git a/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts b/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts
new file mode 100644
index 00000000..9e2356a6
--- /dev/null
+++ b/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts
@@ -0,0 +1,210 @@
+import dayjs from "dayjs";
+import localizedFormat from "dayjs/plugin/localizedFormat";
+import timezone from "dayjs/plugin/timezone";
+import toArray from "dayjs/plugin/toArray";
+import utc from "dayjs/plugin/utc";
+import { createEvent, DateArray, Person } from "ics";
+
+import { getCancelLink } from "@calcom/lib/CalEventParser";
+import { Attendee } from "@calcom/prisma/client";
+import { CalendarEvent } from "@calcom/types/Calendar";
+
+import {
+  emailHead,
+  emailSchedulingBodyHeader,
+  emailBodyLogo,
+  emailScheduledBodyHeaderContent,
+  emailSchedulingBodyDivider,
+} from "./common";
+import OrganizerScheduledEmail from "./organizer-scheduled-email";
+
+dayjs.extend(utc);
+dayjs.extend(timezone);
+dayjs.extend(localizedFormat);
+dayjs.extend(toArray);
+
+export default class AttendeeRequestRescheduledEmail extends OrganizerScheduledEmail {
+  private metadata: { rescheduleLink: string };
+  constructor(calEvent: CalendarEvent, metadata: { rescheduleLink: string }) {
+    super(calEvent);
+    this.metadata = metadata;
+  }
+  protected getNodeMailerPayload(): Record<string, unknown> {
+    const toAddresses = [this.calEvent.attendees[0].email];
+
+    return {
+      icalEvent: {
+        filename: "event.ics",
+        content: this.getiCalEventAsString(),
+      },
+      from: `Cal.com <${this.getMailerOptions().from}>`,
+      to: toAddresses.join(","),
+      subject: `${this.calEvent.organizer.language.translate("requested_to_reschedule_subject_attendee", {
+        eventType: this.calEvent.type,
+        name: this.calEvent.attendees[0].name,
+      })}`,
+      html: this.getHtmlBody(),
+      text: this.getTextBody(),
+    };
+  }
+
+  // @OVERRIDE
+  protected getiCalEventAsString(): string | undefined {
+    console.log("overriding");
+    const icsEvent = createEvent({
+      start: dayjs(this.calEvent.startTime)
+        .utc()
+        .toArray()
+        .slice(0, 6)
+        .map((v, i) => (i === 1 ? v + 1 : v)) as DateArray,
+      startInputType: "utc",
+      productId: "calendso/ics",
+      title: this.calEvent.organizer.language.translate("ics_event_title", {
+        eventType: this.calEvent.type,
+        name: this.calEvent.attendees[0].name,
+      }),
+      description: this.getTextBody(),
+      duration: { minutes: dayjs(this.calEvent.endTime).diff(dayjs(this.calEvent.startTime), "minute") },
+      organizer: { name: this.calEvent.organizer.name, email: this.calEvent.organizer.email },
+      attendees: this.calEvent.attendees.map((attendee: Person) => ({
+        name: attendee.name,
+        email: attendee.email,
+      })),
+      status: "CANCELLED",
+      method: "CANCEL",
+    });
+    if (icsEvent.error) {
+      throw icsEvent.error;
+    }
+    return icsEvent.value;
+  }
+  // @OVERRIDE
+  protected getWhen(): string {
+    return `
+    <p style="height: 6px"></p>
+    <div style="line-height: 6px;">
+      <p style="color: #494949;">${this.calEvent.organizer.language.translate("when")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;text-decoration: line-through;">
+      ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("dddd").toLowerCase()
+      )}, ${this.calEvent.organizer.language.translate(
+      this.getOrganizerStart().format("MMMM").toLowerCase()
+    )} ${this.getOrganizerStart().format("D")}, ${this.getOrganizerStart().format(
+      "YYYY"
+    )} | ${this.getOrganizerStart().format("h:mma")} - ${this.getOrganizerEnd().format(
+      "h:mma"
+    )} <span style="color: #888888">(${this.getTimezone()})</span>
+      </p>
+    </div>`;
+  }
+
+  protected getTextBody(): string {
+    return `
+${this.calEvent.organizer.language.translate("request_reschedule_title_attendee")}
+${this.calEvent.organizer.language.translate("request_reschedule_subtitle", {
+  organizer: this.calEvent.organizer.name,
+})},
+${this.getWhat()}
+${this.getWhen()}
+${this.getAdditionalNotes()}
+${this.calEvent.organizer.language.translate("need_to_reschedule_or_cancel")}
+${getCancelLink(this.calEvent)}
+`.replace(/(<([^>]+)>)/gi, "");
+  }
+
+  protected getHtmlBody(): string {
+    const headerContent = this.calEvent.organizer.language.translate("rescheduled_event_type_subject", {
+      eventType: this.calEvent.type,
+      name: this.calEvent.attendees[0].name,
+      date: `${this.getOrganizerStart().format("h:mma")} - ${this.getOrganizerEnd().format(
+        "h:mma"
+      )}, ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("dddd").toLowerCase()
+      )}, ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("MMMM").toLowerCase()
+      )} ${this.getOrganizerStart().format("D")}, ${this.getOrganizerStart().format("YYYY")}`,
+    });
+
+    return `
+    <!doctype html>
+    <html xmlns="http://www.w3.org/1999/xhtml" xmlns:v="urn:schemas-microsoft-com:vml" xmlns:o="urn:schemas-microsoft-com:office:office">
+    ${emailHead(headerContent)}
+    <body style="word-spacing:normal;background-color:#F5F5F5;">
+      <div style="background-color:#F5F5F5;">
+        ${emailSchedulingBodyHeader("calendarCircle")}
+        ${emailScheduledBodyHeaderContent(
+          this.calEvent.organizer.language.translate("request_reschedule_title_attendee"),
+          this.calEvent.organizer.language.translate("request_reschedule_subtitle", {
+            organizer: this.calEvent.organizer.name,
+          })
+        )}
+        ${emailSchedulingBodyDivider()}
+        <!--[if mso | IE]></td></tr></table><table align="center" border="0" cellpadding="0" cellspacing="0" class="" style="width:600px;" width="600" bgcolor="#FFFFFF" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+        <div style="background:#FFFFFF;background-color:#FFFFFF;margin:0px auto;max-width:600px;">
+          <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#FFFFFF;background-color:#FFFFFF;width:100%;">
+            <tbody>
+              <tr>
+                <td style="border-left:1px solid #E1E1E1;border-right:1px solid #E1E1E1;direction:ltr;font-size:0px;padding:0px;text-align:center;">
+                  <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:598px;" ><![endif]-->
+                  <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+                    <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+                      <tbody>
+                        <tr>
+                          <td align="left" style="font-size:0px;padding:10px 40px;word-break:break-word;">
+                            <div style="font-family:Roboto, Helvetica, sans-serif;font-size:16px;font-weight:500;line-height:1;text-align:left;color:#3E3E3E;">
+                              ${this.getWhat()}
+                              ${this.getWhen()}
+                              ${this.getWho()}
+                              ${this.getAdditionalNotes()}
+                            </div>
+                          </td>
+                        </tr>
+                      </tbody>
+                    </table>
+                  </div>
+                  <!--[if mso | IE]></td></tr></table><![endif]-->
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </div>
+        ${emailSchedulingBodyDivider()}
+        <!--[if mso | IE]></td></tr></table><table align="center" border="0" cellpadding="0" cellspacing="0" class="" style="width:600px;" width="600" bgcolor="#FFFFFF" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+        <div style="background:#FFFFFF;background-color:#FFFFFF;margin:0px auto;max-width:600px;">
+          <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#FFFFFF;background-color:#FFFFFF;width:100%;">
+            <tbody>
+              <tr>
+                <td style="border-bottom:1px solid #E1E1E1;border-left:1px solid #E1E1E1;border-right:1px solid #E1E1E1;direction:ltr;font-size:0px;padding:0px;text-align:center;">
+                  <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:598px;" ><![endif]-->
+                  <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+                    <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+                      <tbody>
+                        <tr>
+                          <td align="left" style="font-size:0px;padding:10px 25px;word-break:break-word;">
+                            <div style="font-family:Roboto, Helvetica, sans-serif;font-size:16px;font-weight:500;text-align:center;color:#3E3E3E;">
+                            <a style="padding: 8px 16px;background-color: #292929;color: white;border-radius: 2px;display: inline-block;margin-bottom: 16px;"
+                              href="${this.metadata.rescheduleLink}" target="_blank"
+                            >
+                              Book a new time
+                              <img src="https://app.cal.com/emails/linkIcon.png" style="width:16px; margin-left: 5px;filter: brightness(0) invert(1); vertical-align: top;" />
+                              </a>
+                            </div>
+                          </td>
+                        </tr>
+                      </tbody>
+                    </table>
+                  </div>
+                  <!--[if mso | IE]></td></tr></table><![endif]-->
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </div>
+        ${emailBodyLogo()}
+        <!--[if mso | IE]></td></tr></table><![endif]-->
+      </div>
+    </body>
+    </html>
+    `;
+  }
+}
diff --git a/apps/web/lib/emails/templates/common/scheduling-body-head.ts b/apps/web/lib/emails/templates/common/scheduling-body-head.ts
index 7f3a6d66..fc715d2a 100644
--- a/apps/web/lib/emails/templates/common/scheduling-body-head.ts
+++ b/apps/web/lib/emails/templates/common/scheduling-body-head.ts
@@ -40,7 +40,7 @@ export const emailSchedulingBodyHeader = (headerType: BodyHeadType): string => {
     <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#FFFFFF;background-color:#FFFFFF;width:100%;">
       <tbody>
         <tr>
-          <td style="border-left:1px solid #E1E1E1;border-right:1px solid #E1E1E1;border-top:1px solid #E1E1E1;direction:ltr;font-size:0px;padding:30px 20px 0 20px;text-align:center;">
+          <td style="border-left:1px solid #E1E1E1;border-right:1px solid #E1E1E1;border-top:1px solid #E1E1E1;direction:ltr;font-size:0px;padding:30px 30px 0 30px;text-align:center;">
             <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:558px;" ><![endif]-->
             <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
               <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
diff --git a/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts b/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts
new file mode 100644
index 00000000..667ca4e3
--- /dev/null
+++ b/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts
@@ -0,0 +1,189 @@
+import dayjs from "dayjs";
+import localizedFormat from "dayjs/plugin/localizedFormat";
+import timezone from "dayjs/plugin/timezone";
+import toArray from "dayjs/plugin/toArray";
+import utc from "dayjs/plugin/utc";
+import { createEvent, DateArray, Person } from "ics";
+
+import { getCancelLink } from "@calcom/lib/CalEventParser";
+import { CalendarEvent } from "@calcom/types/Calendar";
+
+import {
+  emailHead,
+  emailSchedulingBodyHeader,
+  emailBodyLogo,
+  emailScheduledBodyHeaderContent,
+  emailSchedulingBodyDivider,
+} from "./common";
+import OrganizerScheduledEmail from "./organizer-scheduled-email";
+
+dayjs.extend(utc);
+dayjs.extend(timezone);
+dayjs.extend(localizedFormat);
+dayjs.extend(toArray);
+
+export default class OrganizerRequestRescheduledEmail extends OrganizerScheduledEmail {
+  private metadata: { rescheduleLink: string };
+  constructor(calEvent: CalendarEvent, metadata: { rescheduleLink: string }) {
+    super(calEvent);
+    this.metadata = metadata;
+  }
+  protected getNodeMailerPayload(): Record<string, unknown> {
+    const toAddresses = [this.calEvent.organizer.email];
+
+    return {
+      icalEvent: {
+        filename: "event.ics",
+        content: this.getiCalEventAsString(),
+      },
+      from: `Cal.com <${this.getMailerOptions().from}>`,
+      to: toAddresses.join(","),
+      subject: `${this.calEvent.organizer.language.translate("rescheduled_event_type_subject", {
+        eventType: this.calEvent.type,
+        name: this.calEvent.attendees[0].name,
+        date: `${this.getOrganizerStart().format("h:mma")} - ${this.getOrganizerEnd().format(
+          "h:mma"
+        )}, ${this.calEvent.organizer.language.translate(
+          this.getOrganizerStart().format("dddd").toLowerCase()
+        )}, ${this.calEvent.organizer.language.translate(
+          this.getOrganizerStart().format("MMMM").toLowerCase()
+        )} ${this.getOrganizerStart().format("D")}, ${this.getOrganizerStart().format("YYYY")}`,
+      })}`,
+      html: this.getHtmlBody(),
+      text: this.getTextBody(),
+    };
+  }
+
+  // @OVERRIDE
+  protected getiCalEventAsString(): string | undefined {
+    console.log("overriding");
+    const icsEvent = createEvent({
+      start: dayjs(this.calEvent.startTime)
+        .utc()
+        .toArray()
+        .slice(0, 6)
+        .map((v, i) => (i === 1 ? v + 1 : v)) as DateArray,
+      startInputType: "utc",
+      productId: "calendso/ics",
+      title: this.calEvent.organizer.language.translate("ics_event_title", {
+        eventType: this.calEvent.type,
+        name: this.calEvent.attendees[0].name,
+      }),
+      description: this.getTextBody(),
+      duration: { minutes: dayjs(this.calEvent.endTime).diff(dayjs(this.calEvent.startTime), "minute") },
+      organizer: { name: this.calEvent.organizer.name, email: this.calEvent.organizer.email },
+      attendees: this.calEvent.attendees.map((attendee: Person) => ({
+        name: attendee.name,
+        email: attendee.email,
+      })),
+      status: "CANCELLED",
+      method: "CANCEL",
+    });
+    if (icsEvent.error) {
+      throw icsEvent.error;
+    }
+    return icsEvent.value;
+  }
+  // @OVERRIDE
+  protected getWhen(): string {
+    return `
+    <p style="height: 6px"></p>
+    <div style="line-height: 6px;">
+      <p style="color: #494949;">${this.calEvent.organizer.language.translate("when")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;text-decoration: line-through;">
+      ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("dddd").toLowerCase()
+      )}, ${this.calEvent.organizer.language.translate(
+      this.getOrganizerStart().format("MMMM").toLowerCase()
+    )} ${this.getOrganizerStart().format("D")}, ${this.getOrganizerStart().format(
+      "YYYY"
+    )} | ${this.getOrganizerStart().format("h:mma")} - ${this.getOrganizerEnd().format(
+      "h:mma"
+    )} <span style="color: #888888">(${this.getTimezone()})</span>
+      </p>
+    </div>`;
+  }
+
+  protected getTextBody(): string {
+    return `
+${this.calEvent.organizer.language.translate("request_reschedule_title_organizer", {
+  attendee: this.calEvent.attendees[0].name,
+})}
+${this.calEvent.organizer.language.translate("request_reschedule_subtitle_organizer", {
+  attendee: this.calEvent.attendees[0].name,
+})},
+${this.getWhat()}
+${this.getWhen()}
+${this.getLocation()}
+${this.getAdditionalNotes()}
+${this.calEvent.organizer.language.translate("need_to_reschedule_or_cancel")}
+${getCancelLink(this.calEvent)}
+`.replace(/(<([^>]+)>)/gi, "");
+  }
+
+  protected getHtmlBody(): string {
+    const headerContent = this.calEvent.organizer.language.translate("rescheduled_event_type_subject", {
+      eventType: this.calEvent.type,
+      name: this.calEvent.attendees[0].name,
+      date: `${this.getOrganizerStart().format("h:mma")} - ${this.getOrganizerEnd().format(
+        "h:mma"
+      )}, ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("dddd").toLowerCase()
+      )}, ${this.calEvent.organizer.language.translate(
+        this.getOrganizerStart().format("MMMM").toLowerCase()
+      )} ${this.getOrganizerStart().format("D")}, ${this.getOrganizerStart().format("YYYY")}`,
+    });
+
+    return `
+    <!doctype html>
+    <html xmlns="http://www.w3.org/1999/xhtml" xmlns:v="urn:schemas-microsoft-com:vml" xmlns:o="urn:schemas-microsoft-com:office:office">
+    ${emailHead(headerContent)}
+    <body style="word-spacing:normal;background-color:#F5F5F5;">
+      <div style="background-color:#F5F5F5;">
+        ${emailSchedulingBodyHeader("calendarCircle")}
+        ${emailScheduledBodyHeaderContent(
+          this.calEvent.organizer.language.translate("request_reschedule_title_organizer", {
+            attendee: this.calEvent.attendees[0].name,
+          }),
+          this.calEvent.organizer.language.translate("request_reschedule_subtitle_organizer", {
+            attendee: this.calEvent.attendees[0].name,
+          })
+        )}
+        ${emailSchedulingBodyDivider()}
+        <!--[if mso | IE]></td></tr></table><table align="center" border="0" cellpadding="0" cellspacing="0" class="" style="width:600px;" width="600" bgcolor="#FFFFFF" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+        <div style="background:#FFFFFF;background-color:#FFFFFF;margin:0px auto;max-width:600px;">
+          <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#FFFFFF;background-color:#FFFFFF;width:100%;">
+            <tbody>
+              <tr>
+                <td style="border-left:1px solid #E1E1E1;border-right:1px solid #E1E1E1;direction:ltr;font-size:0px;padding:0px;text-align:center;">
+                  <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:598px;" ><![endif]-->
+                  <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+                    <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+                      <tbody>
+                        <tr>
+                          <td align="left" style="font-size:0px;padding:10px 40px;word-break:break-word;">
+                            <div style="font-family:Roboto, Helvetica, sans-serif;font-size:16px;font-weight:500;line-height:1;text-align:left;color:#3E3E3E;">
+                              ${this.getWhat()}
+                              ${this.getWhen()}
+                              ${this.getWho()}
+                              ${this.getAdditionalNotes()}
+                            </div>
+                          </td>
+                        </tr>
+                      </tbody>
+                    </table>
+                  </div>
+                  <!--[if mso | IE]></td></tr></table><![endif]-->
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </div>
+        ${emailBodyLogo()}
+        <!--[if mso | IE]></td></tr></table><![endif]-->
+      </div>
+    </body>
+    </html>
+    `;
+  }
+}
diff --git a/apps/web/lib/getBooking.tsx b/apps/web/lib/getBooking.tsx
new file mode 100644
index 00000000..2c61e93d
--- /dev/null
+++ b/apps/web/lib/getBooking.tsx
@@ -0,0 +1,33 @@
+import { PrismaClient } from "@prisma/client";
+
+import { Prisma } from "@calcom/prisma/client";
+
+async function getBooking(prisma: PrismaClient, uid: string) {
+  const booking = await prisma.booking.findFirst({
+    where: {
+      uid,
+    },
+    select: {
+      startTime: true,
+      description: true,
+      attendees: {
+        select: {
+          email: true,
+          name: true,
+        },
+      },
+    },
+  });
+
+  if (booking) {
+    // @NOTE: had to do this because Server side cant return [Object objects]
+    // probably fixable with json.stringify -> json.parse
+    booking["startTime"] = (booking?.startTime as Date)?.toISOString() as unknown as Date;
+  }
+
+  return booking;
+}
+
+export type GetBookingType = Prisma.PromiseReturnType<typeof getBooking>;
+
+export default getBooking;
diff --git a/apps/web/lib/locationOptions.tsx b/apps/web/lib/locationOptions.tsx
new file mode 100644
index 00000000..c0d3b9d0
--- /dev/null
+++ b/apps/web/lib/locationOptions.tsx
@@ -0,0 +1,30 @@
+import { TFunction } from "next-i18next";
+
+import { LocationType } from "./location";
+
+export const LocationOptionsToString = (location: string, t: TFunction) => {
+  switch (location) {
+    case LocationType.InPerson:
+      return t("set_address_place");
+    case LocationType.Link:
+      return t("set_link_meeting");
+    case LocationType.Phone:
+      return t("cal_invitee_phone_number_scheduling");
+    case LocationType.GoogleMeet:
+      return t("cal_provide_google_meet_location");
+    case LocationType.Zoom:
+      return t("cal_provide_zoom_meeting_url");
+    case LocationType.Daily:
+      return t("cal_provide_video_meeting_url");
+    case LocationType.Jitsi:
+      return t("cal_provide_jitsi_meeting_url");
+    case LocationType.Huddle01:
+      return t("cal_provide_huddle01_meeting_url");
+    case LocationType.Tandem:
+      return t("cal_provide_tandem_meeting_url");
+    case LocationType.Teams:
+      return t("cal_provide_teams_meeting_url");
+    default:
+      return null;
+  }
+};
diff --git a/apps/web/lib/parseDate.ts b/apps/web/lib/parseDate.ts
new file mode 100644
index 00000000..755c98c7
--- /dev/null
+++ b/apps/web/lib/parseDate.ts
@@ -0,0 +1,14 @@
+import dayjs, { Dayjs } from "dayjs";
+import { I18n } from "next-i18next";
+
+import { detectBrowserTimeFormat } from "@lib/timeFormat";
+
+import { parseZone } from "./parseZone";
+
+export const parseDate = (date: string | null | Dayjs, i18n: I18n) => {
+  if (!date) return "No date";
+  const parsedZone = parseZone(date);
+  if (!parsedZone?.isValid()) return "Invalid date";
+  const formattedTime = parsedZone?.format(detectBrowserTimeFormat);
+  return formattedTime + ", " + dayjs(date).toDate().toLocaleString(i18n.language, { dateStyle: "full" });
+};
diff --git a/apps/web/pages/[user]/[type].tsx b/apps/web/pages/[user]/[type].tsx
index 557b5139..6f54f171 100644
--- a/apps/web/pages/[user]/[type].tsx
+++ b/apps/web/pages/[user]/[type].tsx
@@ -8,6 +8,7 @@ import { useLocale } from "@calcom/lib/hooks/useLocale";
 
 import { asStringOrNull } from "@lib/asStringOrNull";
 import { getWorkingHours } from "@lib/availability";
+import getBooking, { GetBookingType } from "@lib/getBooking";
 import prisma from "@lib/prisma";
 import { inferSSRProps } from "@lib/types/inferSSRProps";
 
@@ -48,6 +49,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   const userParam = asStringOrNull(context.query.user);
   const typeParam = asStringOrNull(context.query.type);
   const dateParam = asStringOrNull(context.query.date);
+  const rescheduleUid = asStringOrNull(context.query.rescheduleUid);
 
   if (!userParam || !typeParam) {
     throw new Error(`File is not named [type]/[user]`);
@@ -261,6 +263,11 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   eventTypeObject.schedule = null;
   eventTypeObject.availability = [];
 
+  let booking: GetBookingType | null = null;
+  if (rescheduleUid) {
+    booking = await getBooking(prisma, rescheduleUid);
+  }
+
   const dynamicNames = isDynamicGroup
     ? users.map((user) => {
         return user.name || "";
@@ -302,6 +309,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
       workingHours,
       trpcState: ssr.dehydrate(),
       previousPage: context.req.headers.referer ?? null,
+      booking,
     },
   };
 };
diff --git a/apps/web/pages/[user]/book.tsx b/apps/web/pages/[user]/book.tsx
index 3966bcd9..804a3661 100644
--- a/apps/web/pages/[user]/book.tsx
+++ b/apps/web/pages/[user]/book.tsx
@@ -1,4 +1,3 @@
-import { Prisma } from "@prisma/client";
 import dayjs from "dayjs";
 import timezone from "dayjs/plugin/timezone";
 import utc from "dayjs/plugin/utc";
@@ -15,6 +14,7 @@ import {
 import { useLocale } from "@calcom/lib/hooks/useLocale";
 
 import { asStringOrThrow } from "@lib/asStringOrNull";
+import getBooking, { GetBookingType } from "@lib/getBooking";
 import prisma from "@lib/prisma";
 import { inferSSRProps } from "@lib/types/inferSSRProps";
 
@@ -102,6 +102,7 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
             disableGuests: true,
             users: {
               select: {
+                id: true,
                 username: true,
                 name: true,
                 email: true,
@@ -147,28 +148,9 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
     };
   })[0];
 
-  async function getBooking() {
-    return prisma.booking.findFirst({
-      where: {
-        uid: asStringOrThrow(context.query.rescheduleUid),
-      },
-      select: {
-        description: true,
-        attendees: {
-          select: {
-            email: true,
-            name: true,
-          },
-        },
-      },
-    });
-  }
-
-  type Booking = Prisma.PromiseReturnType<typeof getBooking>;
-  let booking: Booking | null = null;
-
+  let booking: GetBookingType | null = null;
   if (context.query.rescheduleUid) {
-    booking = await getBooking();
+    booking = await getBooking(prisma, context.query.rescheduleUid as string);
   }
 
   const isDynamicGroupBooking = users.length > 1;
diff --git a/apps/web/pages/api/book/confirm.ts b/apps/web/pages/api/book/confirm.ts
index 3e39bde5..64a0b920 100644
--- a/apps/web/pages/api/book/confirm.ts
+++ b/apps/web/pages/api/book/confirm.ts
@@ -169,9 +169,15 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
           metadata.conferenceData = results[0].createdEvent?.conferenceData;
           metadata.entryPoints = results[0].createdEvent?.entryPoints;
         }
-        await sendScheduledEmails({ ...evt, additionInformation: metadata });
+        try {
+          await sendScheduledEmails({ ...evt, additionInformation: metadata });
+        } catch (error) {
+          log.error(error);
+        }
       }
 
+      // @NOTE: be careful with this as if any error occurs before this booking doesn't get confirmed
+      // Should perform update on booking (confirm) -> then trigger the rest handlers
       await prisma.booking.update({
         where: {
           id: bookingId,
diff --git a/apps/web/pages/api/book/event.ts b/apps/web/pages/api/book/event.ts
index 79f7f43c..8c8ef7d7 100644
--- a/apps/web/pages/api/book/event.ts
+++ b/apps/web/pages/api/book/event.ts
@@ -1,4 +1,11 @@
-import { Credential, Prisma, SchedulingType, WebhookTriggerEvents } from "@prisma/client";
+import {
+  BookingStatus,
+  Credential,
+  Payment,
+  Prisma,
+  SchedulingType,
+  WebhookTriggerEvents,
+} from "@prisma/client";
 import async from "async";
 import dayjs from "dayjs";
 import dayjsBusinessTime from "dayjs-business-time";
@@ -12,12 +19,12 @@ import { v5 as uuidv5 } from "uuid";
 import { getBusyCalendarTimes } from "@calcom/core/CalendarManager";
 import EventManager from "@calcom/core/EventManager";
 import { getBusyVideoTimes } from "@calcom/core/videoClient";
-import { getDefaultEvent, getUsernameList } from "@calcom/lib/defaultEvents";
+import { getDefaultEvent, getUsernameList, getGroupName } from "@calcom/lib/defaultEvents";
 import { getErrorFromUnknown } from "@calcom/lib/errors";
 import logger from "@calcom/lib/logger";
 import notEmpty from "@calcom/lib/notEmpty";
 import type { BufferedBusyTime } from "@calcom/types/BufferedBusyTime";
-import type { AdditionInformation, CalendarEvent, EventBusyDate } from "@calcom/types/Calendar";
+import type { AdditionInformation, CalendarEvent, EventBusyDate, Person } from "@calcom/types/Calendar";
 import type { EventResult, PartialReference } from "@calcom/types/EventManager";
 import { handlePayment } from "@ee/lib/stripe/server";
 
@@ -223,7 +230,9 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
   const reqBody = req.body as BookingCreateBody;
 
   // handle dynamic user
-  const dynamicUserList = getUsernameList(reqBody?.user);
+  const dynamicUserList = Array.isArray(reqBody.user)
+    ? getGroupName(req.body.user)
+    : getUsernameList(reqBody.user as string);
   const eventTypeSlug = reqBody.eventTypeSlug;
   const eventTypeId = reqBody.eventTypeId;
   const tAttendees = await getTranslation(reqBody.language ?? "en", "common");
@@ -344,6 +353,7 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
       (str, input) => str + "<br /><br />" + input.label + ":<br />" + input.value,
       ""
     );
+
   const evt: CalendarEvent = {
     type: eventType.title,
     title: getEventName(eventNameObject), //this needs to be either forced in english, or fetched for each attendee and organizer separately
@@ -373,6 +383,41 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
 
   // Initialize EventManager with credentials
   const rescheduleUid = reqBody.rescheduleUid;
+  async function getOriginalRescheduledBooking(uid: string) {
+    return prisma.booking.findFirst({
+      where: {
+        uid,
+        status: {
+          in: [BookingStatus.ACCEPTED, BookingStatus.CANCELLED],
+        },
+      },
+      include: {
+        attendees: {
+          select: {
+            name: true,
+            email: true,
+            locale: true,
+            timeZone: true,
+          },
+        },
+        user: {
+          select: {
+            id: true,
+            name: true,
+            email: true,
+            locale: true,
+            timeZone: true,
+          },
+        },
+        payment: true,
+      },
+    });
+  }
+  type BookingType = Prisma.PromiseReturnType<typeof getOriginalRescheduledBooking>;
+  let originalRescheduledBooking: BookingType = null;
+  if (rescheduleUid) {
+    originalRescheduledBooking = await getOriginalRescheduledBooking(rescheduleUid);
+  }
 
   async function createBooking() {
     // @TODO: check as metadata
@@ -381,6 +426,12 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
       await verifyAccount(web3Details.userSignature, web3Details.userWallet);
     }
 
+    if (originalRescheduledBooking) {
+      evt.title = originalRescheduledBooking?.title || evt.title;
+      evt.description = originalRescheduledBooking?.description || evt.additionalNotes;
+      evt.location = originalRescheduledBooking?.location;
+    }
+
     const eventTypeRel = !eventTypeId
       ? {}
       : {
@@ -392,51 +443,72 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     const dynamicEventSlugRef = !eventTypeId ? eventTypeSlug : null;
     const dynamicGroupSlugRef = !eventTypeId ? (reqBody.user as string).toLowerCase() : null;
 
-    return prisma.booking.create({
+    const newBookingData: Prisma.BookingCreateInput = {
+      uid,
+      title: evt.title,
+      startTime: dayjs(evt.startTime).toDate(),
+      endTime: dayjs(evt.endTime).toDate(),
+      description: evt.additionalNotes,
+      confirmed: (!eventType.requiresConfirmation && !eventType.price) || !!rescheduleUid,
+      location: evt.location,
+      eventType: eventTypeRel,
+      attendees: {
+        createMany: {
+          data: evt.attendees.map((attendee) => {
+            //if attendee is team member, it should fetch their locale not booker's locale
+            //perhaps make email fetch request to see if his locale is stored, else
+            const retObj = {
+              name: attendee.name,
+              email: attendee.email,
+              timeZone: attendee.timeZone,
+              locale: attendee.language.locale,
+            };
+            return retObj;
+          }),
+        },
+      },
+      dynamicEventSlugRef,
+      dynamicGroupSlugRef,
+      user: {
+        connect: {
+          id: users[0].id,
+        },
+      },
+      destinationCalendar: evt.destinationCalendar
+        ? {
+            connect: { id: evt.destinationCalendar.id },
+          }
+        : undefined,
+    };
+    if (originalRescheduledBooking) {
+      newBookingData["paid"] = originalRescheduledBooking.paid;
+      newBookingData["fromReschedule"] = originalRescheduledBooking.uid;
+      if (newBookingData.attendees?.createMany?.data) {
+        newBookingData.attendees.createMany.data = originalRescheduledBooking.attendees;
+      }
+    }
+    const createBookingObj = {
       include: {
         user: {
           select: { email: true, name: true, timeZone: true },
         },
         attendees: true,
+        payment: true,
       },
-      data: {
-        uid,
-        title: evt.title,
-        startTime: dayjs(evt.startTime).toDate(),
-        endTime: dayjs(evt.endTime).toDate(),
-        description: evt.additionalNotes,
-        confirmed: (!eventType.requiresConfirmation && !eventType.price) || !!rescheduleUid,
-        location: evt.location,
-        eventType: eventTypeRel,
-        attendees: {
-          createMany: {
-            data: evt.attendees.map((attendee) => {
-              //if attendee is team member, it should fetch their locale not booker's locale
-              //perhaps make email fetch request to see if his locale is stored, else
-              const retObj = {
-                name: attendee.name,
-                email: attendee.email,
-                timeZone: attendee.timeZone,
-                locale: attendee.language.locale,
-              };
-              return retObj;
-            }),
-          },
-        },
-        dynamicEventSlugRef,
-        dynamicGroupSlugRef,
-        user: {
-          connect: {
-            id: users[0].id,
-          },
-        },
-        destinationCalendar: evt.destinationCalendar
-          ? {
-              connect: { id: evt.destinationCalendar.id },
-            }
-          : undefined,
-      },
-    });
+      data: newBookingData,
+    };
+
+    if (originalRescheduledBooking?.paid && originalRescheduledBooking?.payment) {
+      const bookingPayment = originalRescheduledBooking?.payment?.find((payment) => payment.success);
+
+      if (bookingPayment) {
+        createBookingObj.data.payment = {
+          connect: { id: bookingPayment.id },
+        };
+      }
+    }
+
+    return prisma.booking.create(createBookingObj);
   }
 
   let results: EventResult[] = [];
@@ -569,9 +641,9 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
   const credentials = await refreshCredentials(user.credentials);
   const eventManager = new EventManager({ ...user, credentials });
 
-  if (rescheduleUid) {
+  if (originalRescheduledBooking?.uid) {
     // Use EventManager to conditionally use all needed integrations.
-    const updateManager = await eventManager.update(evt, rescheduleUid);
+    const updateManager = await eventManager.update(evt, originalRescheduledBooking.uid, booking.id);
     // This gets overridden when updating the event - to check if notes have been hidden or not. We just reset this back
     // to the default description when we are sending the emails.
     evt.description = eventType.description;
@@ -615,7 +687,6 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
 
     results = createManager.results;
     referencesToCreate = createManager.referencesToCreate;
-
     if (results.length > 0 && results.every((res) => !res.success)) {
       const error = {
         errorCode: "BookingCreatingMeetingFailed",
@@ -641,9 +712,10 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     await sendAttendeeRequestEmail(evt, attendeesList[0]);
   }
 
-  if (typeof eventType.price === "number" && eventType.price > 0) {
+  if (typeof eventType.price === "number" && eventType.price > 0 && !originalRescheduledBooking?.paid) {
     try {
       const [firstStripeCredential] = user.credentials.filter((cred) => cred.type == "stripe_payment");
+
       if (!booking.user) booking.user = user;
       const payment = await handlePayment(evt, eventType, firstStripeCredential, booking);
 
diff --git a/apps/web/pages/api/book/request-reschedule.ts b/apps/web/pages/api/book/request-reschedule.ts
new file mode 100644
index 00000000..0c321678
--- /dev/null
+++ b/apps/web/pages/api/book/request-reschedule.ts
@@ -0,0 +1,217 @@
+import { BookingStatus, User, Booking, Attendee, BookingReference } from "@prisma/client";
+import dayjs from "dayjs";
+import type { NextApiRequest, NextApiResponse } from "next";
+import { getSession } from "next-auth/react";
+import type { TFunction } from "next-i18next";
+import { z, ZodError } from "zod";
+
+import { getCalendar } from "@calcom/core/CalendarManager";
+import EventManager from "@calcom/core/EventManager";
+import { CalendarEventBuilder } from "@calcom/core/builders/CalendarEvent/builder";
+import { CalendarEventDirector } from "@calcom/core/builders/CalendarEvent/director";
+import { deleteMeeting } from "@calcom/core/videoClient";
+import { getTranslation } from "@calcom/lib/server/i18n";
+import { Person } from "@calcom/types/Calendar";
+
+import { sendRequestRescheduleEmail } from "@lib/emails/email-manager";
+import prisma from "@lib/prisma";
+
+export type RescheduleResponse = Booking & {
+  attendees: Attendee[];
+};
+export type PersonAttendeeCommonFields = Pick<
+  User,
+  "id" | "email" | "name" | "locale" | "timeZone" | "username"
+>;
+
+const rescheduleSchema = z.object({
+  bookingId: z.string(),
+  rescheduleReason: z.string().optional(),
+});
+
+const findUserOwnerByUserId = async (userId: number) => {
+  return await prisma.user.findUnique({
+    rejectOnNotFound: true,
+    where: {
+      id: userId,
+    },
+    select: {
+      id: true,
+      name: true,
+      username: true,
+      email: true,
+      timeZone: true,
+      locale: true,
+      credentials: true,
+      destinationCalendar: true,
+    },
+  });
+};
+
+const handler = async (
+  req: NextApiRequest,
+  res: NextApiResponse
+): Promise<RescheduleResponse | NextApiResponse | void> => {
+  const session = await getSession({ req });
+  const {
+    bookingId,
+    rescheduleReason: cancellationReason,
+  }: { bookingId: string; rescheduleReason: string; cancellationReason: string } = req.body;
+  let userOwner: Awaited<ReturnType<typeof findUserOwnerByUserId>>;
+  try {
+    if (session?.user?.id) {
+      userOwner = await findUserOwnerByUserId(session?.user.id);
+    } else {
+      return res.status(501);
+    }
+
+    const bookingToReschedule = await prisma.booking.findFirst({
+      select: {
+        id: true,
+        uid: true,
+        title: true,
+        startTime: true,
+        endTime: true,
+        eventTypeId: true,
+        location: true,
+        attendees: true,
+        references: true,
+      },
+      rejectOnNotFound: true,
+      where: {
+        uid: bookingId,
+        NOT: {
+          status: {
+            in: [BookingStatus.CANCELLED, BookingStatus.REJECTED],
+          },
+        },
+      },
+    });
+
+    if (bookingToReschedule && bookingToReschedule.eventTypeId && userOwner) {
+      const event = await prisma.eventType.findFirst({
+        select: {
+          title: true,
+          users: true,
+          schedulingType: true,
+        },
+        rejectOnNotFound: true,
+        where: {
+          id: bookingToReschedule.eventTypeId,
+        },
+      });
+      await prisma.booking.update({
+        where: {
+          id: bookingToReschedule.id,
+        },
+        data: {
+          rescheduled: true,
+          cancellationReason,
+          status: BookingStatus.CANCELLED,
+          updatedAt: dayjs().toISOString(),
+        },
+      });
+
+      const [mainAttendee] = bookingToReschedule.attendees;
+      // @NOTE: Should we assume attendees language?
+      const tAttendees = await getTranslation(mainAttendee.locale ?? "en", "common");
+      const usersToPeopleType = (
+        users: PersonAttendeeCommonFields[],
+        selectedLanguage: TFunction
+      ): Person[] => {
+        return users?.map((user) => {
+          return {
+            email: user.email || "",
+            name: user.name || "",
+            username: user?.username || "",
+            language: { translate: selectedLanguage, locale: user.locale || "en" },
+            timeZone: user?.timeZone,
+          };
+        });
+      };
+
+      const userOwnerTranslation = await getTranslation(userOwner.locale ?? "en", "common");
+      const [userOwnerAsPeopleType] = usersToPeopleType([userOwner], userOwnerTranslation);
+
+      const builder = new CalendarEventBuilder();
+      builder.init({
+        title: bookingToReschedule.title,
+        type: event.title,
+        startTime: bookingToReschedule.startTime.toISOString(),
+        endTime: bookingToReschedule.endTime.toISOString(),
+        attendees: usersToPeopleType(
+          // username field doesn't exists on attendee but could be in the future
+          bookingToReschedule.attendees as unknown as PersonAttendeeCommonFields[],
+          tAttendees
+        ),
+        organizer: userOwnerAsPeopleType,
+      });
+
+      const director = new CalendarEventDirector();
+      director.setBuilder(builder);
+      director.setExistingBooking(bookingToReschedule as unknown as Booking);
+      director.setCancellationReason(cancellationReason);
+      await director.buildForRescheduleEmail();
+
+      // Handling calendar and videos cancellation
+      // This can set previous time as available, until virtual calendar is done
+      const credentialsMap = new Map();
+      userOwner.credentials.forEach((credential) => {
+        credentialsMap.set(credential.type, credential);
+      });
+      const bookingRefsFiltered: BookingReference[] = bookingToReschedule.references.filter(
+        (ref) => !!credentialsMap.get(ref.type)
+      );
+      bookingRefsFiltered.forEach((bookingRef) => {
+        if (bookingRef.uid) {
+          if (bookingRef.type.endsWith("_calendar")) {
+            const calendar = getCalendar(credentialsMap.get(bookingRef.type));
+
+            return calendar?.deleteEvent(bookingRef.uid, builder.calendarEvent);
+          } else if (bookingRef.type.endsWith("_video")) {
+            return deleteMeeting(credentialsMap.get(bookingRef.type), bookingRef.uid);
+          }
+        }
+      });
+
+      // Creating cancelled event as placeholders in calendars, remove when virtual calendar handles it
+      const eventManager = new EventManager({
+        credentials: userOwner.credentials,
+        destinationCalendar: userOwner.destinationCalendar,
+      });
+      builder.calendarEvent.title = `Cancelled: ${builder.calendarEvent.title}`;
+      await eventManager.updateAndSetCancelledPlaceholder(builder.calendarEvent, bookingToReschedule);
+
+      // Send emails
+      await sendRequestRescheduleEmail(builder.calendarEvent, {
+        rescheduleLink: builder.rescheduleLink,
+      });
+    }
+
+    return res.status(200).json(bookingToReschedule);
+  } catch (error) {
+    throw new Error("Error.request.reschedule");
+  }
+};
+
+function validate(
+  handler: (req: NextApiRequest, res: NextApiResponse) => Promise<RescheduleResponse | NextApiResponse | void>
+) {
+  return async (req: NextApiRequest, res: NextApiResponse) => {
+    if (req.method === "POST") {
+      try {
+        rescheduleSchema.parse(req.body);
+      } catch (error) {
+        if (error instanceof ZodError && error?.name === "ZodError") {
+          return res.status(400).json(error?.issues);
+        }
+        return res.status(402);
+      }
+    } else {
+      return res.status(405);
+    }
+    await handler(req, res);
+  };
+}
+
+export default validate(handler);
diff --git a/apps/web/pages/bookings/[status].tsx b/apps/web/pages/bookings/[status].tsx
index 717d9164..07a98418 100644
--- a/apps/web/pages/bookings/[status].tsx
+++ b/apps/web/pages/bookings/[status].tsx
@@ -2,11 +2,11 @@ import { CalendarIcon } from "@heroicons/react/outline";
 import { useRouter } from "next/router";
 import { Fragment } from "react";
 
+import { useLocale } from "@calcom/lib/hooks/useLocale";
 import { Alert } from "@calcom/ui/Alert";
 import Button from "@calcom/ui/Button";
 
 import { useInViewObserver } from "@lib/hooks/useInViewObserver";
-import { useLocale } from "@lib/hooks/useLocale";
 import { inferQueryInput, trpc } from "@lib/trpc";
 
 import BookingsShell from "@components/BookingsShell";
diff --git a/apps/web/pages/cancel/[uid].tsx b/apps/web/pages/cancel/[uid].tsx
index 3f64966e..538d81f6 100644
--- a/apps/web/pages/cancel/[uid].tsx
+++ b/apps/web/pages/cancel/[uid].tsx
@@ -101,8 +101,8 @@ export default function Type(props: inferSSRProps<typeof getServerSideProps>) {
                           className="mb-5 sm:mb-6"
                         />
                         <div className="space-x-2 text-center rtl:space-x-reverse">
-                          <Button color="secondary" onClick={() => router.push("/reschedule/" + uid)}>
-                            {t("reschedule_this")}
+                          <Button color="secondary" onClick={() => router.back()}>
+                            {t("back_to_bookings")}
                           </Button>
                           <Button
                             data-testid="cancel"
diff --git a/apps/web/pages/cancel/success.tsx b/apps/web/pages/cancel/success.tsx
index e2c2af98..64dba79d 100644
--- a/apps/web/pages/cancel/success.tsx
+++ b/apps/web/pages/cancel/success.tsx
@@ -1,5 +1,5 @@
 import { CheckIcon } from "@heroicons/react/outline";
-import { ArrowRightIcon } from "@heroicons/react/solid";
+import { ArrowLeftIcon } from "@heroicons/react/solid";
 import { useSession } from "next-auth/react";
 import { useRouter } from "next/router";
 
@@ -52,7 +52,7 @@ export default function CancelSuccess() {
                   <div className="mt-5">
                     {!loading && !session?.user && <Button href={eventPage as string}>Pick another</Button>}
                     {!loading && session?.user && (
-                      <Button data-testid="back-to-bookings" href="/bookings" EndIcon={ArrowRightIcon}>
+                      <Button data-testid="back-to-bookings" href="/bookings" StartIcon={ArrowLeftIcon}>
                         {t("back_to_bookings")}
                       </Button>
                     )}
diff --git a/apps/web/pages/success.tsx b/apps/web/pages/success.tsx
index 9f07efbd..4b88e1c5 100644
--- a/apps/web/pages/success.tsx
+++ b/apps/web/pages/success.tsx
@@ -1,5 +1,5 @@
 import { CheckIcon } from "@heroicons/react/outline";
-import { ClockIcon, XIcon } from "@heroicons/react/solid";
+import { ArrowLeftIcon, ClockIcon, XIcon } from "@heroicons/react/solid";
 import classNames from "classnames";
 import dayjs from "dayjs";
 import timezone from "dayjs/plugin/timezone";
@@ -7,6 +7,7 @@ import toArray from "dayjs/plugin/toArray";
 import utc from "dayjs/plugin/utc";
 import { createEvent } from "ics";
 import { GetServerSidePropsContext } from "next";
+import { useSession } from "next-auth/react";
 import Link from "next/link";
 import { useRouter } from "next/router";
 import { useEffect, useState, useRef } from "react";
@@ -133,6 +134,7 @@ export default function Success(props: inferSSRProps<typeof getServerSideProps>)
   const { location: _location, name, reschedule } = router.query;
   const location = Array.isArray(_location) ? _location[0] : _location;
   const [is24h, setIs24h] = useState(isBrowserLocale24h());
+  const { data: session } = useSession();
 
   const [date, setDate] = useState(dayjs.utc(asStringOrThrow(router.query.date)));
   const { isReady, Theme } = useTheme(props.profile.theme);
@@ -200,7 +202,7 @@ export default function Success(props: inferSSRProps<typeof getServerSideProps>)
 
     return encodeURIComponent(event.value ? event.value : false);
   }
-
+  const userIsOwner = !!(session?.user?.id && eventType.users.find((user) => (user.id = session.user.id)));
   return (
     (isReady && (
       <div
@@ -268,8 +270,8 @@ export default function Success(props: inferSSRProps<typeof getServerSideProps>)
                         </div>
                         {location && (
                           <>
-                            <div className="font-medium">{t("where")}</div>
-                            <div className="col-span-2">
+                            <div className="mt-6 font-medium">{t("where")}</div>
+                            <div className="col-span-2 mt-6">
                               {location.startsWith("http") ? (
                                 <a title="Meeting Link" href={location}>
                                   {location}
@@ -382,7 +384,7 @@ export default function Success(props: inferSSRProps<typeof getServerSideProps>)
                       </div>
                     </div>
                   )}
-                  {!props.hideBranding && (
+                  {!(userIsOwner || props.hideBranding) && (
                     <div className="border-bookinglightest text-booking-lighter pt-4 text-center text-xs dark:border-gray-900 dark:text-white">
                       <a href="https://cal.com/signup">{t("create_booking_link_with_calcom")}</a>
 
@@ -405,6 +407,15 @@ export default function Success(props: inferSSRProps<typeof getServerSideProps>)
                       </form>
                     </div>
                   )}
+                  {userIsOwner && (
+                    <div className="mt-4">
+                      <Link href="/bookings">
+                        <a className="flex items-center text-black dark:text-white">
+                          <ArrowLeftIcon className="mr-1 h-4 w-4" /> {t("back_to_bookings")}
+                        </a>
+                      </Link>
+                    </div>
+                  )}
                 </div>
               </div>
             </div>
@@ -432,6 +443,7 @@ const getEventTypesFromDB = async (typeId: number) => {
       successRedirectUrl: true,
       users: {
         select: {
+          id: true,
           name: true,
           hideBranding: true,
           plan: true,
@@ -478,6 +490,7 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
         id: eventType.userId,
       },
       select: {
+        id: true,
         name: true,
         hideBranding: true,
         plan: true,
diff --git a/apps/web/pages/team/[slug]/[type].tsx b/apps/web/pages/team/[slug]/[type].tsx
index e8bf0039..8f15f1be 100644
--- a/apps/web/pages/team/[slug]/[type].tsx
+++ b/apps/web/pages/team/[slug]/[type].tsx
@@ -5,6 +5,7 @@ import { UserPlan } from "@calcom/prisma/client";
 
 import { asStringOrNull } from "@lib/asStringOrNull";
 import { getWorkingHours } from "@lib/availability";
+import getBooking, { GetBookingType } from "@lib/getBooking";
 import prisma from "@lib/prisma";
 import { inferSSRProps } from "@lib/types/inferSSRProps";
 
@@ -20,6 +21,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   const slugParam = asStringOrNull(context.query.slug);
   const typeParam = asStringOrNull(context.query.type);
   const dateParam = asStringOrNull(context.query.date);
+  const rescheduleUid = asStringOrNull(context.query.rescheduleUid);
 
   if (!slugParam || !typeParam) {
     throw new Error(`File is not named [idOrSlug]/[user]`);
@@ -110,6 +112,11 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
 
   eventTypeObject.availability = [];
 
+  let booking: GetBookingType | null = null;
+  if (rescheduleUid) {
+    booking = await getBooking(prisma, rescheduleUid);
+  }
+
   return {
     props: {
       // Team is always pro
@@ -127,6 +134,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
       eventType: eventTypeObject,
       workingHours,
       previousPage: context.req.headers.referer ?? null,
+      booking,
     },
   };
 };
diff --git a/apps/web/pages/team/[slug]/book.tsx b/apps/web/pages/team/[slug]/book.tsx
index 442c8c9e..faa08311 100644
--- a/apps/web/pages/team/[slug]/book.tsx
+++ b/apps/web/pages/team/[slug]/book.tsx
@@ -5,6 +5,7 @@ import { JSONObject } from "superjson/dist/types";
 import { getLocationLabels } from "@calcom/app-store/utils";
 
 import { asStringOrThrow } from "@lib/asStringOrNull";
+import getBooking, { GetBookingType } from "@lib/getBooking";
 import prisma from "@lib/prisma";
 import { inferSSRProps } from "@lib/types/inferSSRProps";
 
@@ -56,6 +57,7 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
       },
       users: {
         select: {
+          id: true,
           avatar: true,
           name: true,
         },
@@ -74,28 +76,9 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
     };
   })[0];
 
-  async function getBooking() {
-    return prisma.booking.findFirst({
-      where: {
-        uid: asStringOrThrow(context.query.rescheduleUid),
-      },
-      select: {
-        description: true,
-        attendees: {
-          select: {
-            email: true,
-            name: true,
-          },
-        },
-      },
-    });
-  }
-
-  type Booking = Prisma.PromiseReturnType<typeof getBooking>;
-  let booking: Booking | null = null;
-
+  let booking: GetBookingType | null = null;
   if (context.query.rescheduleUid) {
-    booking = await getBooking();
+    booking = await getBooking(prisma, context.query.rescheduleUid as string);
   }
 
   const t = await getTranslation(context.locale ?? "en", "common");
diff --git a/apps/web/playwright/booking-pages.test.ts b/apps/web/playwright/booking-pages.test.ts
index 6c54ab66..6c0115b0 100644
--- a/apps/web/playwright/booking-pages.test.ts
+++ b/apps/web/playwright/booking-pages.test.ts
@@ -109,6 +109,7 @@ test.describe("pro user", () => {
 
     await page.goto("/bookings/upcoming");
     await page.locator('[data-testid="reschedule"]').click();
+    await page.locator('[data-testid="edit"]').click();
     await page.waitForNavigation({
       url: (url) => {
         const bookingId = url.searchParams.get("rescheduleUid");
diff --git a/apps/web/playwright/dynamic-booking-pages.test.ts b/apps/web/playwright/dynamic-booking-pages.test.ts
index 5eba38df..ec3a3fb0 100644
--- a/apps/web/playwright/dynamic-booking-pages.test.ts
+++ b/apps/web/playwright/dynamic-booking-pages.test.ts
@@ -43,6 +43,7 @@ test.describe("dynamic booking", () => {
     // Logged in
     await page.goto("/bookings/upcoming");
     await page.locator('[data-testid="reschedule"]').click();
+    await page.locator('[data-testid="edit"]').click();
     await page.waitForNavigation({
       url: (url) => {
         const bookingId = url.searchParams.get("rescheduleUid");
diff --git a/apps/web/playwright/integrations-stripe.test.ts b/apps/web/playwright/integrations-stripe.test.ts
index f2a2f52c..f6426591 100644
--- a/apps/web/playwright/integrations-stripe.test.ts
+++ b/apps/web/playwright/integrations-stripe.test.ts
@@ -13,6 +13,7 @@ test.describe.serial("Stripe integration", () => {
   test.afterAll(() => {
     teardown.deleteAllPaymentsByEmail("pro@example.com");
     teardown.deleteAllBookingsByEmail("pro@example.com");
+    teardown.deleteAllPaymentCredentialsByEmail("pro@example.com");
   });
   test.skip(!IS_STRIPE_ENABLED, "It should only run if Stripe is installed");
 
diff --git a/apps/web/playwright/lib/dbSetup.ts b/apps/web/playwright/lib/dbSetup.ts
new file mode 100644
index 00000000..8837f785
--- /dev/null
+++ b/apps/web/playwright/lib/dbSetup.ts
@@ -0,0 +1,80 @@
+import { Booking } from "@prisma/client";
+import dayjs from "dayjs";
+import utc from "dayjs/plugin/utc";
+import short from "short-uuid";
+import { v5 as uuidv5, v4 as uuidv4 } from "uuid";
+
+dayjs.extend(utc);
+
+const translator = short();
+
+const TestUtilCreateBookingOnUserId = async (
+  userId: number,
+  username: string,
+  eventTypeId: number,
+  { confirmed = true, rescheduled = false, paid = false, status = "ACCEPTED" }: Partial<Booking>
+) => {
+  const startDate = dayjs().add(1, "day").toDate();
+  const seed = `${username}:${dayjs(startDate).utc().format()}:${new Date().getTime()}`;
+  const uid = translator.fromUUID(uuidv5(seed, uuidv5.URL));
+  return await prisma?.booking.create({
+    data: {
+      uid: uid,
+      title: "30min",
+      startTime: startDate,
+      endTime: dayjs().add(1, "day").add(30, "minutes").toDate(),
+      user: {
+        connect: {
+          id: userId,
+        },
+      },
+      attendees: {
+        create: {
+          email: "attendee@example.com",
+          name: "Attendee Example",
+          timeZone: "Europe/London",
+        },
+      },
+      eventType: {
+        connect: {
+          id: eventTypeId,
+        },
+      },
+      confirmed,
+      rescheduled,
+      paid,
+      status,
+    },
+    select: {
+      id: true,
+      uid: true,
+      user: true,
+    },
+  });
+};
+
+const TestUtilCreatePayment = async (
+  bookingId: number,
+  { success = false, refunded = false }: { success?: boolean; refunded?: boolean }
+) => {
+  return await prisma?.payment.create({
+    data: {
+      uid: uuidv4(),
+      amount: 20000,
+      fee: 160,
+      currency: "usd",
+      success,
+      refunded,
+      type: "STRIPE",
+      data: {},
+      externalId: "DEMO_PAYMENT_FROM_DB",
+      booking: {
+        connect: {
+          id: bookingId,
+        },
+      },
+    },
+  });
+};
+
+export { TestUtilCreateBookingOnUserId, TestUtilCreatePayment };
diff --git a/apps/web/playwright/lib/teardown.ts b/apps/web/playwright/lib/teardown.ts
index 51fbbb61..18e63172 100644
--- a/apps/web/playwright/lib/teardown.ts
+++ b/apps/web/playwright/lib/teardown.ts
@@ -1,11 +1,17 @@
+import { Prisma } from "@prisma/client";
+
 import prisma from "@lib/prisma";
 
-export const deleteAllBookingsByEmail = async (email: string) =>
+export const deleteAllBookingsByEmail = async (
+  email: string,
+  whereConditional: Prisma.BookingWhereInput = {}
+) =>
   prisma.booking.deleteMany({
     where: {
       user: {
         email,
       },
+      ...whereConditional,
     },
   });
 
@@ -38,3 +44,20 @@ export const deleteAllPaymentsByEmail = async (email: string) => {
     },
   });
 };
+
+export const deleteAllPaymentCredentialsByEmail = async (email: string) => {
+  await prisma.user.update({
+    where: {
+      email,
+    },
+    data: {
+      credentials: {
+        deleteMany: {
+          type: {
+            endsWith: "_payment",
+          },
+        },
+      },
+    },
+  });
+};
diff --git a/apps/web/playwright/reschedule.test.ts b/apps/web/playwright/reschedule.test.ts
new file mode 100644
index 00000000..695d6d25
--- /dev/null
+++ b/apps/web/playwright/reschedule.test.ts
@@ -0,0 +1,246 @@
+import { expect, test } from "@playwright/test";
+import { BookingStatus } from "@prisma/client";
+import dayjs from "dayjs";
+
+import { TestUtilCreateBookingOnUserId, TestUtilCreatePayment } from "./lib/dbSetup";
+import { deleteAllBookingsByEmail } from "./lib/teardown";
+import { selectFirstAvailableTimeSlotNextMonth } from "./lib/testUtils";
+
+const IS_STRIPE_ENABLED = !!(
+  process.env.STRIPE_CLIENT_ID &&
+  process.env.NEXT_PUBLIC_STRIPE_PUBLIC_KEY &&
+  process.env.STRIPE_PRIVATE_KEY
+);
+const findUserByEmail = async (email: string) => {
+  return await prisma?.user.findFirst({
+    select: {
+      id: true,
+      email: true,
+      username: true,
+      credentials: true,
+    },
+    where: {
+      email,
+    },
+  });
+};
+test.describe("Reschedule Tests", async () => {
+  let currentUser: Awaited<ReturnType<typeof findUserByEmail>>;
+  // Using logged in state from globalSetup
+  test.use({ storageState: "playwright/artifacts/proStorageState.json" });
+  test.beforeAll(async () => {
+    currentUser = await findUserByEmail("pro@example.com");
+  });
+  test.afterEach(async () => {
+    try {
+      await deleteAllBookingsByEmail("pro@example.com", {
+        createdAt: { gte: dayjs().startOf("day").toISOString() },
+      });
+    } catch (error) {
+      console.log("Error while trying to delete all bookings from pro user");
+    }
+  });
+
+  test("Should do a booking request reschedule from /bookings", async ({ page }) => {
+    const user = currentUser;
+    const eventType = await prisma?.eventType.findFirst({
+      where: {
+        userId: user?.id,
+        slug: "30min",
+      },
+    });
+    let originalBooking;
+    if (user && user.id && user.username && eventType) {
+      originalBooking = await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+        status: BookingStatus.ACCEPTED,
+      });
+    }
+
+    await page.goto("/bookings/upcoming");
+
+    await page.locator('[data-testid="reschedule"]').click();
+
+    await page.locator('[data-testid="reschedule_request"]').click();
+
+    await page.fill('[data-testid="reschedule_reason"]', "I can't longer have it");
+
+    await page.locator('button[data-testid="send_request"]').click();
+
+    await page.goto("/bookings/cancelled");
+
+    // Find booking that was recently cancelled
+    const booking = await prisma?.booking.findFirst({
+      select: {
+        id: true,
+        uid: true,
+        cancellationReason: true,
+        status: true,
+        rescheduled: true,
+      },
+      where: { id: originalBooking?.id },
+    });
+
+    expect(booking?.rescheduled).toBe(true);
+    expect(booking?.cancellationReason).toBe("I can't longer have it");
+    expect(booking?.status).toBe(BookingStatus.CANCELLED);
+  });
+
+  test("Should display former time when rescheduling availability", async ({ page }) => {
+    const user = currentUser;
+    const eventType = await prisma?.eventType.findFirst({
+      where: {
+        userId: user?.id,
+        slug: "30min",
+      },
+    });
+    let originalBooking;
+    if (user && user.id && user.username && eventType) {
+      originalBooking = await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+        status: BookingStatus.CANCELLED,
+        rescheduled: true,
+      });
+    }
+
+    await page.goto(
+      `/${originalBooking?.user?.username}/${eventType?.slug}?rescheduleUid=${originalBooking?.uid}`
+    );
+    const formerTimeElement = await page.locator('[data-testid="former_time_p"]');
+    await expect(formerTimeElement).toBeVisible();
+  });
+
+  test("Should display request reschedule send on bookings/cancelled", async ({ page }) => {
+    const user = currentUser;
+    const eventType = await prisma?.eventType.findFirst({
+      where: {
+        userId: user?.id,
+        slug: "30min",
+      },
+    });
+
+    if (user && user.id && user.username && eventType) {
+      await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+        status: BookingStatus.CANCELLED,
+        rescheduled: true,
+      });
+    }
+    await page.goto("/bookings/cancelled");
+
+    const requestRescheduleSentElement = await page.locator('[data-testid="request_reschedule_sent"]').nth(1);
+    await expect(requestRescheduleSentElement).toBeVisible();
+  });
+
+  test("Should do a reschedule from user owner", async ({ page }) => {
+    const user = currentUser;
+
+    const eventType = await prisma?.eventType.findFirst({
+      where: {
+        userId: user?.id,
+      },
+    });
+    if (user?.id && user?.username && eventType?.id) {
+      const booking = await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+        rescheduled: true,
+        status: BookingStatus.CANCELLED,
+      });
+
+      await page.goto(`/${user?.username}/${eventType?.slug}?rescheduleUid=${booking?.uid}`);
+
+      await selectFirstAvailableTimeSlotNextMonth(page);
+
+      await expect(page.locator('[name="name"]')).toBeDisabled();
+      await expect(page.locator('[name="email"]')).toBeDisabled();
+      await expect(page.locator('[name="notes"]')).toBeDisabled();
+
+      await page.locator('[data-testid="confirm-reschedule-button"]').click();
+
+      await page.waitForNavigation({
+        url(url) {
+          return url.pathname.endsWith("/success");
+        },
+      });
+
+      await expect(page).toHaveURL(/.*success/);
+
+      // NOTE: remove if old booking should not be deleted
+      const oldBooking = await prisma?.booking.findFirst({ where: { id: booking?.id } });
+      expect(oldBooking).toBeNull();
+
+      const newBooking = await prisma?.booking.findFirst({ where: { fromReschedule: booking?.uid } });
+      expect(newBooking).not.toBeNull();
+    }
+  });
+
+  test("Unpaid rescheduling should go to payment page", async ({ page }) => {
+    let user = currentUser;
+
+    test.skip(
+      IS_STRIPE_ENABLED && !(user && user.credentials.length > 0),
+      "Skipped as stripe is not installed and user is missing credentials"
+    );
+
+    const eventType = await prisma?.eventType.findFirst({
+      where: {
+        userId: user?.id,
+        slug: "paid",
+      },
+    });
+    if (user?.id && user?.username && eventType?.id) {
+      const booking = await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+        rescheduled: true,
+        status: BookingStatus.CANCELLED,
+        paid: false,
+      });
+      if (booking?.id) {
+        await TestUtilCreatePayment(booking.id, {});
+        await page.goto(`/${user?.username}/${eventType?.slug}?rescheduleUid=${booking?.uid}`);
+
+        await selectFirstAvailableTimeSlotNextMonth(page);
+
+        await page.locator('[data-testid="confirm-reschedule-button"]').click();
+
+        await page.waitForNavigation({
+          url(url) {
+            return url.pathname.indexOf("/payment") > -1;
+          },
+        });
+
+        await expect(page).toHaveURL(/.*payment/);
+      }
+    }
+  });
+
+  test("Paid rescheduling should go to success page", async ({ page }) => {
+    let user = currentUser;
+    try {
+      const eventType = await prisma?.eventType.findFirst({
+        where: {
+          userId: user?.id,
+          slug: "paid",
+        },
+      });
+      if (user?.id && user?.username && eventType?.id) {
+        const booking = await TestUtilCreateBookingOnUserId(user?.id, user?.username, eventType?.id, {
+          rescheduled: true,
+          status: BookingStatus.CANCELLED,
+          paid: true,
+        });
+        if (booking?.id) {
+          await TestUtilCreatePayment(booking.id, {});
+          await page.goto(`/${user?.username}/${eventType?.slug}?rescheduleUid=${booking?.uid}`);
+
+          await selectFirstAvailableTimeSlotNextMonth(page);
+
+          await page.locator('[data-testid="confirm-reschedule-button"]').click();
+
+          await expect(page).toHaveURL(/.*success/);
+        }
+      }
+    } catch (error) {
+      await prisma?.payment.delete({
+        where: {
+          externalId: "DEMO_PAYMENT_FROM_DB",
+        },
+      });
+    }
+  });
+});
diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index cb3b43be..ab12bd5c 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -66,6 +66,11 @@
   "your_meeting_has_been_booked": "Your meeting has been booked",
   "event_type_has_been_rescheduled_on_time_date": "Your {{eventType}} with {{name}} has been rescheduled to {{time}} ({{timeZone}}) on {{date}}.",
   "event_has_been_rescheduled": "Updated - Your event has been rescheduled",
+  "request_reschedule_title_attendee": "Request to reschedule your booking",
+  "request_reschedule_subtitle": "{{organizer}} has cancelled the booking and requested you to pick another time.",
+  "request_reschedule_title_organizer": "You have requested {{attendee}} to reschedule",
+  "request_reschedule_subtitle_organizer": "You have cancelled the booking and {{attendee}} should be pick a new booking time with you.",
+  "reschedule_reason": "Reason for reschedule",
   "hi_user_name": "Hi {{name}}",
   "ics_event_title": "{{eventType}} with {{name}}",
   "new_event_subject": "New event: {{attendeeName}} - {{date}} - {{eventType}}",
@@ -84,6 +89,7 @@
   "meeting_url": "Meeting URL",
   "meeting_request_rejected": "Your meeting request has been rejected",
   "rescheduled_event_type_subject": "Rescheduled: {{eventType}} with {{name}} at {{date}}",
+  "requested_to_reschedule_subject_attendee": "Action Required Reschedule: Please book a new to time for {{eventType}} with {{name}}",
   "rejected_event_type_with_organizer": "Rejected: {{eventType}} with {{organizer}} on {{date}}",
   "hi": "Hi",
   "join_team": "Join team",
@@ -411,7 +417,7 @@
   "booking_confirmation": "Confirm your {{eventTypeTitle}} with {{profileName}}",
   "booking_reschedule_confirmation": "Reschedule your {{eventTypeTitle}} with {{profileName}}",
   "in_person_meeting": "In-person meeting",
-  "link_meeting":"Link meeting",
+  "link_meeting": "Link meeting",
   "phone_call": "Phone call",
   "phone_number": "Phone Number",
   "enter_phone_number": "Enter phone number",
@@ -720,5 +726,15 @@
   "external_redirect_url": "https://example.com/redirect-to-my-success-page",
   "redirect_url_upgrade_description": "In order to use this feature, you need to upgrade to a Pro account.",
   "duplicate": "Duplicate",
-  "you_can_manage_your_schedules": "You can manage your schedules on the Availability page."
+  "you_can_manage_your_schedules": "You can manage your schedules on the Availability page.",
+  "request_reschedule_booking": "Request to reschedule your booking",
+  "reason_for_reschedule": "Reason for reschedule",
+  "book_a_new_time": "Book a new time",
+  "reschedule_request_sent": "Reschedule request sent",
+  "reschedule_modal_description": "This will cancel the scheduled meeting, notify the scheduler and ask them to pick a new time.",
+  "reason_for_reschedule_request": "Reason for reschedule request",
+  "send_reschedule_request": "Send reschedule request",
+  "edit_booking": "Edit booking",
+  "reschedule_booking": "Reschedule booking",
+  "former_time": "Former time"
 }
diff --git a/apps/web/server/routers/viewer.tsx b/apps/web/server/routers/viewer.tsx
index 3f32214a..2eaa0fc8 100644
--- a/apps/web/server/routers/viewer.tsx
+++ b/apps/web/server/routers/viewer.tsx
@@ -393,6 +393,7 @@ const loggedInViewerRouter = createProtectedRouter()
               id: true,
             },
           },
+          rescheduled: true,
         },
         orderBy,
         take: take + 1,
diff --git a/apps/web/styles/globals.css b/apps/web/styles/globals.css
index a2b646b9..d3e54f5d 100644
--- a/apps/web/styles/globals.css
+++ b/apps/web/styles/globals.css
@@ -13,20 +13,20 @@
  * Override the default tailwindcss-forms styling (default is: 'colors.blue.600')
  * @see: https://github.com/tailwindlabs/tailwindcss-forms/issues/14#issuecomment-1005376006 
  */
-[type='text']:focus,
-[type='email']:focus,
-[type='url']:focus,
-[type='password']:focus,
-[type='number']:focus,
-[type='date']:focus,
-[type='datetime-local']:focus,
-[type='month']:focus,
-[type='search']:focus,
-[type='tel']:focus,
-[type='checkbox']:focus,
-[type='radio']:focus,
-[type='time']:focus,
-[type='week']:focus,
+[type="text"]:focus,
+[type="email"]:focus,
+[type="url"]:focus,
+[type="password"]:focus,
+[type="number"]:focus,
+[type="date"]:focus,
+[type="datetime-local"]:focus,
+[type="month"]:focus,
+[type="search"]:focus,
+[type="tel"]:focus,
+[type="checkbox"]:focus,
+[type="radio"]:focus,
+[type="time"]:focus,
+[type="week"]:focus,
 [multiple]:focus,
 textarea:focus,
 select:focus {
@@ -217,7 +217,7 @@ button[role="switch"][data-state="checked"] span {
 }
 
 .react-multi-email > [type="text"] {
-  @apply block w-full rounded-md border-gray-300 shadow-sm dark:border-gray-900 dark:bg-gray-700 dark:text-white sm:text-sm;
+  @apply focus:border-brand block w-full rounded-[2px] border-gray-300 shadow-sm focus:ring-black dark:border-gray-900 dark:bg-gray-700 dark:text-white sm:text-sm;
 }
 
 .react-multi-email [data-tag] {
diff --git a/apps/website b/apps/website
index e3409f6a..fb5ce134 160000
--- a/apps/website
+++ b/apps/website
@@ -1 +1 @@
-Subproject commit e3409f6aff7e615e061826184a9de8eea3f38cbe
+Subproject commit fb5ce134e57d708cb46036c53d91bbb1f33072af
diff --git a/packages/core/EventManager.ts b/packages/core/EventManager.ts
index bf1289ac..899edb1c 100644
--- a/packages/core/EventManager.ts
+++ b/packages/core/EventManager.ts
@@ -161,7 +161,11 @@ export default class EventManager {
    *
    * @param event
    */
-  public async update(event: CalendarEvent, rescheduleUid: string): Promise<CreateUpdateResult> {
+  public async update(
+    event: CalendarEvent,
+    rescheduleUid: string,
+    newBookingId?: number
+  ): Promise<CreateUpdateResult> {
     const evt = processLocation(event);
 
     if (!rescheduleUid) {
@@ -187,6 +191,7 @@ export default class EventManager {
           },
         },
         destinationCalendar: true,
+        payment: true,
       },
     });
 
@@ -210,6 +215,23 @@ export default class EventManager {
     // Update all calendar events.
     results.push(...(await this.updateAllCalendarEvents(evt, booking)));
 
+    const bookingPayment = booking?.payment;
+
+    // Updating all payment to new
+    if (bookingPayment && newBookingId) {
+      const paymentIds = bookingPayment.map((payment) => payment.id);
+      await prisma.payment.updateMany({
+        where: {
+          id: {
+            in: paymentIds,
+          },
+        },
+        data: {
+          bookingId: newBookingId,
+        },
+      });
+    }
+
     // Now we can delete the old booking and its references.
     const bookingReferenceDeletes = prisma.bookingReference.deleteMany({
       where: {
@@ -345,4 +367,16 @@ export default class EventManager {
       return Promise.reject("No suitable credentials given for the requested integration name.");
     }
   }
+
+  /**
+   * Update event to set a cancelled event placeholder on users calendar
+   * remove if virtual calendar is already done and user availability its read from there
+   * and not only in their calendars
+   * @param event
+   * @param booking
+   * @public
+   */
+  public async updateAndSetCancelledPlaceholder(event: CalendarEvent, booking: PartialBooking) {
+    await this.updateAllCalendarEvents(event, booking);
+  }
 }
diff --git a/packages/core/builders/CalendarEvent/builder.ts b/packages/core/builders/CalendarEvent/builder.ts
new file mode 100644
index 00000000..d6ff8108
--- /dev/null
+++ b/packages/core/builders/CalendarEvent/builder.ts
@@ -0,0 +1,283 @@
+import { Prisma } from "@prisma/client";
+import dayjs from "dayjs";
+import short from "short-uuid";
+import { v5 as uuidv5 } from "uuid";
+
+import { getTranslation } from "@calcom/lib/server/i18n";
+import prisma from "@calcom/prisma";
+
+import { CalendarEventClass } from "./class";
+
+const translator = short();
+const userSelect = Prisma.validator<Prisma.UserArgs>()({
+  select: {
+    id: true,
+    email: true,
+    name: true,
+    username: true,
+    timeZone: true,
+    credentials: true,
+    bufferTime: true,
+    destinationCalendar: true,
+    locale: true,
+  },
+});
+
+type User = Prisma.UserGetPayload<typeof userSelect>;
+type PersonAttendeeCommonFields = Pick<User, "id" | "email" | "name" | "locale" | "timeZone" | "username">;
+interface ICalendarEventBuilder {
+  calendarEvent: CalendarEventClass;
+  eventType: Awaited<ReturnType<CalendarEventBuilder["getEventFromEventId"]>>;
+  users: Awaited<ReturnType<CalendarEventBuilder["getUserById"]>>[];
+  attendeesList: PersonAttendeeCommonFields[];
+  teamMembers: Awaited<ReturnType<CalendarEventBuilder["getTeamMembers"]>>;
+  rescheduleLink: string;
+}
+
+export class CalendarEventBuilder implements ICalendarEventBuilder {
+  calendarEvent!: CalendarEventClass;
+  eventType!: ICalendarEventBuilder["eventType"];
+  users!: ICalendarEventBuilder["users"];
+  attendeesList: ICalendarEventBuilder["attendeesList"] = [];
+  teamMembers: ICalendarEventBuilder["teamMembers"] = [];
+  rescheduleLink!: string;
+
+  constructor() {
+    this.reset();
+  }
+
+  private reset() {
+    this.calendarEvent = new CalendarEventClass();
+  }
+
+  public init(initProps: CalendarEventClass) {
+    this.calendarEvent = new CalendarEventClass(initProps);
+  }
+
+  public setEventType(eventType: ICalendarEventBuilder["eventType"]) {
+    this.eventType = eventType;
+  }
+
+  public async buildEventObjectFromInnerClass(eventId: number) {
+    const resultEvent = await this.getEventFromEventId(eventId);
+    if (resultEvent) {
+      this.eventType = resultEvent;
+    }
+  }
+
+  public async buildUsersFromInnerClass() {
+    if (!this.eventType) {
+      throw new Error("exec BuildEventObjectFromInnerClass before calling this function");
+    }
+    let users = this.eventType.users;
+
+    /* If this event was pre-relationship migration */
+    if (!users.length && this.eventType.userId) {
+      const eventTypeUser = await this.getUserById(this.eventType.userId);
+      if (!eventTypeUser) {
+        throw new Error("buildUsersFromINnerClass.eventTypeUser.notFound");
+      }
+      users.push(eventTypeUser);
+    }
+    this.users = users;
+  }
+
+  public buildAttendeesList() {
+    // Language Function was set on builder init
+    this.attendeesList = [
+      ...(this.calendarEvent.attendees as unknown as PersonAttendeeCommonFields[]),
+      ...this.teamMembers,
+    ];
+  }
+
+  private async getUserById(userId: number) {
+    let resultUser: User | null;
+    try {
+      resultUser = await prisma.user.findUnique({
+        rejectOnNotFound: true,
+        where: {
+          id: userId,
+        },
+        ...userSelect,
+      });
+    } catch (error) {
+      throw new Error("getUsersById.users.notFound");
+    }
+    return resultUser;
+  }
+
+  private async getEventFromEventId(eventTypeId: number) {
+    let resultEventType;
+    try {
+      resultEventType = await prisma.eventType.findUnique({
+        rejectOnNotFound: true,
+        where: {
+          id: eventTypeId,
+        },
+        select: {
+          id: true,
+          users: userSelect,
+          team: {
+            select: {
+              id: true,
+              name: true,
+              slug: true,
+            },
+          },
+          slug: true,
+          teamId: true,
+          title: true,
+          length: true,
+          eventName: true,
+          schedulingType: true,
+          periodType: true,
+          periodStartDate: true,
+          periodEndDate: true,
+          periodDays: true,
+          periodCountCalendarDays: true,
+          requiresConfirmation: true,
+          userId: true,
+          price: true,
+          currency: true,
+          metadata: true,
+          destinationCalendar: true,
+          hideCalendarNotes: true,
+        },
+      });
+    } catch (error) {
+      throw new Error("Error while getting eventType");
+    }
+    return resultEventType;
+  }
+
+  public async buildLuckyUsers() {
+    if (!this.eventType && this.users && this.users.length) {
+      throw new Error("exec buildUsersFromInnerClass before calling this function");
+    }
+
+    // @TODO: user?.username gets flagged as null somehow, maybe a filter before map?
+    const filterUsernames = this.users.filter((user) => user && typeof user.username === "string");
+    const userUsernames = filterUsernames.map((user) => user.username) as string[]; // @TODO: hack
+    const users = await prisma.user.findMany({
+      where: {
+        username: { in: userUsernames },
+        eventTypes: {
+          some: {
+            id: this.eventType.id,
+          },
+        },
+      },
+      select: {
+        id: true,
+        username: true,
+        locale: true,
+      },
+    });
+
+    const userNamesWithBookingCounts = await Promise.all(
+      users.map(async (user) => ({
+        username: user.username,
+        bookingCount: await prisma.booking.count({
+          where: {
+            user: {
+              id: user.id,
+            },
+            startTime: {
+              gt: new Date(),
+            },
+            eventTypeId: this.eventType.id,
+          },
+        }),
+      }))
+    );
+    const luckyUsers = this.getLuckyUsers(this.users, userNamesWithBookingCounts);
+    this.users = luckyUsers;
+  }
+
+  private getLuckyUsers(
+    users: User[],
+    bookingCounts: {
+      username: string | null;
+      bookingCount: number;
+    }[]
+  ) {
+    if (!bookingCounts.length) users.slice(0, 1);
+
+    const [firstMostAvailableUser] = bookingCounts.sort((a, b) => (a.bookingCount > b.bookingCount ? 1 : -1));
+    const luckyUser = users.find((user) => user.username === firstMostAvailableUser?.username);
+    return luckyUser ? [luckyUser] : users;
+  }
+
+  public async buildTeamMembers() {
+    this.teamMembers = await this.getTeamMembers();
+  }
+
+  private async getTeamMembers() {
+    // Users[0] its organizer so we are omitting with slice(1)
+    const teamMemberPromises = this.users.slice(1).map(async function (user) {
+      return {
+        id: user.id,
+        username: user.username,
+        email: user.email || "", // @NOTE: Should we change this "" to teamMemberId?
+        name: user.name || "",
+        timeZone: user.timeZone,
+        language: {
+          translate: await getTranslation(user.locale ?? "en", "common"),
+          locale: user.locale ?? "en",
+        },
+        locale: user.locale,
+      } as PersonAttendeeCommonFields;
+    });
+    return await Promise.all(teamMemberPromises);
+  }
+
+  public buildUIDCalendarEvent() {
+    if (this.users && this.users.length > 0) {
+      throw new Error("call buildUsers before calling this function");
+    }
+    const [mainOrganizer] = this.users;
+    const seed = `${mainOrganizer.username}:${dayjs(this.calendarEvent.startTime)
+      .utc()
+      .format()}:${new Date().getTime()}`;
+    const uid = translator.fromUUID(uuidv5(seed, uuidv5.URL));
+    this.calendarEvent.uid = uid;
+  }
+
+  public setLocation(location: CalendarEventClass["location"]) {
+    this.calendarEvent.location = location;
+  }
+
+  public setUId(uid: CalendarEventClass["uid"]) {
+    this.calendarEvent.uid = uid;
+  }
+
+  public setDestinationCalendar(destinationCalendar: CalendarEventClass["destinationCalendar"]) {
+    this.calendarEvent.destinationCalendar = destinationCalendar;
+  }
+
+  public setHideCalendarNotes(hideCalendarNotes: CalendarEventClass["hideCalendarNotes"]) {
+    this.calendarEvent.hideCalendarNotes = hideCalendarNotes;
+  }
+
+  public setDescription(description: CalendarEventClass["description"]) {
+    this.calendarEvent.description = description;
+  }
+
+  public setCancellationReason(cancellationReason: CalendarEventClass["cancellationReason"]) {
+    this.calendarEvent.cancellationReason = cancellationReason;
+  }
+
+  public buildRescheduleLink(originalBookingUId: string) {
+    if (!this.eventType) {
+      throw new Error("Run buildEventObjectFromInnerClass before this function");
+    }
+    const isTeam = !!this.eventType.teamId;
+
+    const queryParams = new URLSearchParams();
+    queryParams.set("rescheduleUid", `${originalBookingUId}`);
+    const rescheduleLink = `${process.env.NEXT_PUBLIC_WEBAPP_URL}/${
+      isTeam ? `/team/${this.eventType.team?.slug}` : this.users[0].username
+    }/${this.eventType.slug}?${queryParams.toString()}`;
+    this.rescheduleLink = rescheduleLink;
+  }
+}
diff --git a/packages/core/builders/CalendarEvent/class.ts b/packages/core/builders/CalendarEvent/class.ts
new file mode 100644
index 00000000..d433bda2
--- /dev/null
+++ b/packages/core/builders/CalendarEvent/class.ts
@@ -0,0 +1,31 @@
+import { AdditionInformation, CalendarEvent, ConferenceData, Person } from "@calcom/types/Calendar";
+
+import { DestinationCalendar } from ".prisma/client";
+
+class CalendarEventClass implements CalendarEvent {
+  type!: string;
+  title!: string;
+  startTime!: string;
+  endTime!: string;
+  organizer!: Person;
+  attendees!: Person[];
+  description?: string | null;
+  team?: { name: string; members: string[] };
+  location?: string | null;
+  conferenceData?: ConferenceData;
+  additionInformation?: AdditionInformation;
+  uid?: string | null;
+  videoCallData?: any;
+  paymentInfo?: any;
+  destinationCalendar?: DestinationCalendar | null;
+  cancellationReason?: string | null;
+  rejectionReason?: string | null;
+  hideCalendarNotes?: boolean;
+
+  constructor(initProps?: CalendarEvent) {
+    // If more parameters are given we update this
+    Object.assign(this, initProps);
+  }
+}
+
+export { CalendarEventClass };
diff --git a/packages/core/builders/CalendarEvent/director.ts b/packages/core/builders/CalendarEvent/director.ts
new file mode 100644
index 00000000..0eda82f9
--- /dev/null
+++ b/packages/core/builders/CalendarEvent/director.ts
@@ -0,0 +1,35 @@
+import { Booking } from "@prisma/client";
+
+import { CalendarEventBuilder } from "./builder";
+
+export class CalendarEventDirector {
+  private builder!: CalendarEventBuilder;
+  private existingBooking!: Partial<Booking>;
+  private cancellationReason!: string;
+
+  public setBuilder(builder: CalendarEventBuilder): void {
+    this.builder = builder;
+  }
+
+  public setExistingBooking(booking: Booking) {
+    this.existingBooking = booking;
+  }
+
+  public setCancellationReason(reason: string) {
+    this.cancellationReason = reason;
+  }
+
+  public async buildForRescheduleEmail(): Promise<void> {
+    if (this.existingBooking && this.existingBooking.eventTypeId && this.existingBooking.uid) {
+      await this.builder.buildEventObjectFromInnerClass(this.existingBooking.eventTypeId);
+      await this.builder.buildUsersFromInnerClass();
+      this.builder.buildAttendeesList();
+      this.builder.setLocation(this.existingBooking.location);
+      this.builder.setUId(this.existingBooking.uid);
+      this.builder.setCancellationReason(this.cancellationReason);
+      this.builder.buildRescheduleLink(this.existingBooking.uid);
+    } else {
+      throw new Error("buildForRescheduleEmail.missing.params.required");
+    }
+  }
+}
diff --git a/packages/core/tsconfig.json b/packages/core/tsconfig.json
index 184d5dec..39577403 100644
--- a/packages/core/tsconfig.json
+++ b/packages/core/tsconfig.json
@@ -3,6 +3,6 @@
   "compilerOptions": {
     "baseUrl": "."
   },
-  "include": ["."],
+  "include": [".", "../types/*.d.ts"],
   "exclude": ["dist", "build", "node_modules"]
 }
diff --git a/packages/prisma/index.ts b/packages/prisma/index.ts
index 1f92195d..0cf3363f 100644
--- a/packages/prisma/index.ts
+++ b/packages/prisma/index.ts
@@ -1,5 +1,7 @@
 import { PrismaClient } from "@prisma/client";
 
+import { bookingReferenceMiddleware } from "./middleware";
+
 declare global {
   var prisma: PrismaClient | undefined;
 }
@@ -13,5 +15,7 @@ export const prisma =
 if (process.env.NODE_ENV !== "production") {
   globalThis.prisma = prisma;
 }
+// If any changed on middleware server restart is required
+bookingReferenceMiddleware(prisma);
 
 export default prisma;
diff --git a/packages/prisma/middleware/bookingReference.ts b/packages/prisma/middleware/bookingReference.ts
new file mode 100644
index 00000000..a2c771ff
--- /dev/null
+++ b/packages/prisma/middleware/bookingReference.ts
@@ -0,0 +1,51 @@
+import { PrismaClient } from "@prisma/client";
+
+async function middleware(prisma: PrismaClient) {
+  /***********************************/
+  /* SOFT DELETE MIDDLEWARE */
+  /***********************************/
+  prisma.$use(async (params, next) => {
+    // Check incoming query type
+
+    if (params.model === "BookingReference") {
+      if (params.action === "delete") {
+        // Delete queries
+        // Change action to an update
+        params.action = "update";
+        params.args["data"] = { deleted: true };
+      }
+      if (params.action === "deleteMany") {
+        console.log("deletingMany");
+        // Delete many queries
+        params.action = "updateMany";
+        if (params.args.data !== undefined) {
+          params.args.data["deleted"] = true;
+        } else {
+          params.args["data"] = { deleted: true };
+        }
+      }
+      if (params.action === "findUnique") {
+        // Change to findFirst - you cannot filter
+        // by anything except ID / unique with findUnique
+        params.action = "findFirst";
+        // Add 'deleted' filter
+        // ID filter maintained
+        params.args.where["deleted"] = null;
+      }
+      if (params.action === "findMany" || params.action === "findFirst") {
+        // Find many queries
+        if (params.args.where !== undefined) {
+          if (params.args.where.deleted === undefined) {
+            // Exclude deleted records if they have not been explicitly requested
+            params.args.where["deleted"] = null;
+          }
+        } else {
+          params.args["where"] = { deleted: null };
+        }
+      }
+    }
+    return next(params);
+  });
+}
+
+export default middleware;
diff --git a/packages/prisma/middleware/index.ts b/packages/prisma/middleware/index.ts
new file mode 100644
index 00000000..90097ed1
--- /dev/null
+++ b/packages/prisma/middleware/index.ts
@@ -0,0 +1 @@
+export { default as bookingReferenceMiddleware } from "./bookingReference";
diff --git a/packages/prisma/migrations/20220323033335_reschedule_fields_to_bookings_table/migration.sql b/packages/prisma/migrations/20220323033335_reschedule_fields_to_bookings_table/migration.sql
new file mode 100644
index 00000000..e539b327
--- /dev/null
+++ b/packages/prisma/migrations/20220323033335_reschedule_fields_to_bookings_table/migration.sql
@@ -0,0 +1,3 @@
+-- AlterTable
+ALTER TABLE "Booking" ADD COLUMN     "fromReschedule" TEXT,
+ADD COLUMN     "rescheduled" BOOLEAN;
\ No newline at end of file
diff --git a/packages/prisma/migrations/20220328185001_soft_delete_booking_references/migration.sql b/packages/prisma/migrations/20220328185001_soft_delete_booking_references/migration.sql
new file mode 100644
index 00000000..6e561ef0
--- /dev/null
+++ b/packages/prisma/migrations/20220328185001_soft_delete_booking_references/migration.sql
@@ -0,0 +1,2 @@
+-- AlterTable
+ALTER TABLE "BookingReference" ADD COLUMN     "deleted" BOOLEAN;
diff --git a/packages/prisma/migrations/20220412172742_payment_on_delete_cascade/migration.sql b/packages/prisma/migrations/20220412172742_payment_on_delete_cascade/migration.sql
new file mode 100644
index 00000000..0070f627
--- /dev/null
+++ b/packages/prisma/migrations/20220412172742_payment_on_delete_cascade/migration.sql
@@ -0,0 +1,5 @@
+-- DropForeignKey
+ALTER TABLE "Payment" DROP CONSTRAINT "Payment_bookingId_fkey";
+
+-- AddForeignKey
+ALTER TABLE "Payment" ADD CONSTRAINT "Payment_bookingId_fkey" FOREIGN KEY ("bookingId") REFERENCES "Booking"("id") ON DELETE CASCADE ON UPDATE CASCADE;
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 3153a2b2..9e206f2d 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -204,8 +204,9 @@ model BookingReference {
   meetingId       String?
   meetingPassword String?
   meetingUrl      String?
-  booking         Booking? @relation(fields: [bookingId], references: [id])
+  booking         Booking? @relation(fields: [bookingId], references: [id], onDelete: Cascade)
   bookingId       Int?
+  deleted         Boolean?
 }
 
 model Attendee {
@@ -260,6 +261,8 @@ model Booking {
   rejectionReason     String?
   dynamicEventSlugRef String?
   dynamicGroupSlugRef String?
+  rescheduled         Boolean?
+  fromReschedule      String?
 }
 
 model Schedule {
@@ -342,7 +345,7 @@ model Payment {
   uid        String      @unique
   type       PaymentType
   bookingId  Int
-  booking    Booking?    @relation(fields: [bookingId], references: [id])
+  booking    Booking?    @relation(fields: [bookingId], references: [id], onDelete: Cascade)
   amount     Int
   fee        Int
   currency   String
diff --git a/packages/types/Calendar.d.ts b/packages/types/Calendar.d.ts
index 00b9ab3f..f6cc7356 100644
--- a/packages/types/Calendar.d.ts
+++ b/packages/types/Calendar.d.ts
@@ -12,6 +12,8 @@ export type Person = {
   email: string;
   timeZone: string;
   language: { translate: TFunction; locale: string };
+  username?: string;
+  id?: string;
 };
 
 export type EventBusyDate = Record<"start" | "end", Date | string>;
@@ -70,11 +72,14 @@ export interface AdditionInformation {
   hangoutLink?: string;
 }
 
+// If modifying this interface, probably should update builders/calendarEvent files
 export interface CalendarEvent {
   type: string;
   title: string;
   startTime: string;
   endTime: string;
+  organizer: Person;
+  attendees: Person[];
   additionalNotes?: string | null;
   description?: string | null;
   team?: {
@@ -82,8 +87,6 @@ export interface CalendarEvent {
     members: string[];
   };
   location?: string | null;
-  organizer: Person;
-  attendees: Person[];
   conferenceData?: ConferenceData;
   additionInformation?: AdditionInformation;
   uid?: string | null;