diff --git a/apps/web/lib/reschedule/[uid]/getServerSideProps.ts b/apps/web/lib/reschedule/[uid]/getServerSideProps.ts
index fe3974642fb30c..6dcee9ab629e81 100644
--- a/apps/web/lib/reschedule/[uid]/getServerSideProps.ts
+++ b/apps/web/lib/reschedule/[uid]/getServerSideProps.ts
@@ -95,6 +95,18 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
     } as const;
   }
 
+  const eventType = booking.eventType ? booking.eventType : getDefaultEvent(dynamicEventSlugRef);
+
+  const enrichedBookingUser = booking.user
+    ? await UserRepository.enrichUserWithItsProfile({ user: booking.user })
+    : null;
+
+  const eventUrl = await buildEventUrlFromBooking({
+    eventType,
+    dynamicGroupSlugRef: booking.dynamicGroupSlugRef ?? null,
+    profileEnrichedBookingUser: enrichedBookingUser,
+  });
+
   // If booking is already CANCELLED or REJECTED, we can't reschedule this booking. Take the user to the booking page which would show it's correct status and other details.
   // A booking that has been rescheduled to a new booking will also have a status of CANCELLED
   if (
@@ -103,7 +115,7 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
   ) {
     return {
       redirect: {
-        destination: `/booking/${uid}`,
+        destination: booking.status === BookingStatus.CANCELLED ? `${eventUrl}` : `/booking/${uid}`,
         permanent: false,
       },
     };
@@ -118,18 +130,6 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
     };
   }
 
-  const eventType = booking.eventType ? booking.eventType : getDefaultEvent(dynamicEventSlugRef);
-
-  const enrichedBookingUser = booking.user
-    ? await UserRepository.enrichUserWithItsProfile({ user: booking.user })
-    : null;
-
-  const eventUrl = await buildEventUrlFromBooking({
-    eventType,
-    dynamicGroupSlugRef: booking.dynamicGroupSlugRef ?? null,
-    profileEnrichedBookingUser: enrichedBookingUser,
-  });
-
   const isBookingInPast = booking.endTime && new Date(booking.endTime) < new Date();
   if (isBookingInPast) {
     const destinationUrlSearchParams = new URLSearchParams();
@@ -180,6 +180,10 @@ export async function getServerSideProps(context: GetServerSidePropsContext) {
 
   destinationUrlSearchParams.set("rescheduleUid", seatReferenceUid || bookingUid);
 
+  if (allowRescheduleForCancelledBooking) {
+    destinationUrlSearchParams.set("allowRescheduleForCancelledBooking", "true");
+  }
+
   // TODO: I think we should just forward all the query params here including coep flag
   if (coepFlag) {
     destinationUrlSearchParams.set("flag.coep", coepFlag as string);
diff --git a/apps/web/lib/team/[slug]/[type]/getServerSideProps.tsx b/apps/web/lib/team/[slug]/[type]/getServerSideProps.tsx
index fd0fa3ab48ac9d..dcb75b30c0364a 100644
--- a/apps/web/lib/team/[slug]/[type]/getServerSideProps.tsx
+++ b/apps/web/lib/team/[slug]/[type]/getServerSideProps.tsx
@@ -29,6 +29,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   const session = await getServerSession({ req });
   const { slug: teamSlug, type: meetingSlug } = paramsSchema.parse(params);
   const { rescheduleUid, isInstantMeeting: queryIsInstantMeeting, email } = query;
+  const allowRescheduleForCancelledBooking = query.allowRescheduleForCancelledBooking === "true";
   const { currentOrgDomain, isValidOrgDomain } = orgDomainConfig(req, params?.orgSlug);
   const isOrgContext = currentOrgDomain && isValidOrgDomain;
 
@@ -162,7 +163,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   let booking: GetBookingType | null = null;
   if (rescheduleUid) {
     booking = await getBookingForReschedule(`${rescheduleUid}`, session?.user?.id);
-    if (booking?.status === BookingStatus.CANCELLED) {
+    if (booking?.status === BookingStatus.CANCELLED && !allowRescheduleForCancelledBooking) {
       return {
         redirect: {
           permanent: false,
diff --git a/apps/web/server/lib/[user]/[type]/getServerSideProps.ts b/apps/web/server/lib/[user]/[type]/getServerSideProps.ts
index 04e295dc1d2d81..a2c184b086883b 100644
--- a/apps/web/server/lib/[user]/[type]/getServerSideProps.ts
+++ b/apps/web/server/lib/[user]/[type]/getServerSideProps.ts
@@ -51,10 +51,12 @@ async function processReschedule({
   props,
   rescheduleUid,
   session,
+  allowRescheduleForCancelledBooking,
 }: {
   props: Props;
   session: Session | null;
   rescheduleUid: string | string[] | undefined;
+  allowRescheduleForCancelledBooking?: boolean;
 }) {
   if (!rescheduleUid) return;
   const booking = await getBookingForReschedule(`${rescheduleUid}`, session?.user?.id);
@@ -62,7 +64,8 @@ async function processReschedule({
   if (
     booking === null ||
     !booking.eventTypeId ||
-    (booking?.eventTypeId === props.eventData?.id && booking.status !== BookingStatus.CANCELLED)
+    (booking?.eventTypeId === props.eventData?.id &&
+      (booking.status !== BookingStatus.CANCELLED || allowRescheduleForCancelledBooking))
   ) {
     props.booking = booking;
     props.rescheduleUid = Array.isArray(rescheduleUid) ? rescheduleUid[0] : rescheduleUid;
@@ -93,13 +96,15 @@ async function processReschedule({
 async function processSeatedEvent({
   props,
   bookingUid,
+  allowRescheduleForCancelledBooking,
 }: {
   props: Props;
   bookingUid: string | string[] | undefined;
+  allowRescheduleForCancelledBooking?: boolean;
 }) {
   if (!bookingUid) return;
   const booking = await getBookingForSeatedEvent(`${bookingUid}`);
-  if (booking?.status === BookingStatus.CANCELLED) {
+  if (booking?.status === BookingStatus.CANCELLED && !allowRescheduleForCancelledBooking) {
     return {
       redirect: {
         permanent: false,
@@ -116,7 +121,7 @@ async function getDynamicGroupPageProps(context: GetServerSidePropsContext) {
   const session = await getServerSession(context);
   const { user: usernames, type: slug } = paramsSchema.parse(context.params);
   const { rescheduleUid, bookingUid } = context.query;
-
+  const allowRescheduleForCancelledBooking = context.query.allowRescheduleForCancelledBooking === "true";
   const { ssrInit } = await import("@server/lib/ssr");
   const ssr = await ssrInit(context);
   const { currentOrgDomain, isValidOrgDomain } = orgDomainConfig(context.req, context.params?.orgSlug);
@@ -192,12 +197,21 @@ async function getDynamicGroupPageProps(context: GetServerSidePropsContext) {
   };
 
   if (rescheduleUid) {
-    const processRescheduleResult = await processReschedule({ props, rescheduleUid, session });
+    const processRescheduleResult = await processReschedule({
+      props,
+      rescheduleUid,
+      session,
+      allowRescheduleForCancelledBooking,
+    });
     if (processRescheduleResult) {
       return processRescheduleResult;
     }
   } else if (bookingUid) {
-    const processSeatResult = await processSeatedEvent({ props, bookingUid });
+    const processSeatResult = await processSeatedEvent({
+      props,
+      bookingUid,
+      allowRescheduleForCancelledBooking,
+    });
     if (processSeatResult) {
       return processSeatResult;
     }
@@ -213,6 +227,7 @@ async function getUserPageProps(context: GetServerSidePropsContext) {
   const { user: usernames, type: slug } = paramsSchema.parse(context.params);
   const username = usernames[0];
   const { rescheduleUid, bookingUid } = context.query;
+  const allowRescheduleForCancelledBooking = context.query.allowRescheduleForCancelledBooking === "true";
   const { currentOrgDomain, isValidOrgDomain } = orgDomainConfig(context.req, context.params?.orgSlug);
 
   const isOrgContext = currentOrgDomain && isValidOrgDomain;
@@ -289,14 +304,22 @@ async function getUserPageProps(context: GetServerSidePropsContext) {
     rescheduleUid: null,
     orgBannerUrl: eventData?.owner?.profile?.organization?.bannerUrl ?? null,
   };
-
   if (rescheduleUid) {
-    const processRescheduleResult = await processReschedule({ props, rescheduleUid, session });
+    const processRescheduleResult = await processReschedule({
+      props,
+      rescheduleUid,
+      session,
+      allowRescheduleForCancelledBooking,
+    });
     if (processRescheduleResult) {
       return processRescheduleResult;
     }
   } else if (bookingUid) {
-    const processSeatResult = await processSeatedEvent({ props, bookingUid });
+    const processSeatResult = await processSeatedEvent({
+      props,
+      bookingUid,
+      allowRescheduleForCancelledBooking,
+    });
     if (processSeatResult) {
       return processSeatResult;
     }