diff --git a/apps/web/components/booking/pages/BookingPage.tsx b/apps/web/components/booking/pages/BookingPage.tsx
index f02c3deda8..458561742c 100644
--- a/apps/web/components/booking/pages/BookingPage.tsx
+++ b/apps/web/components/booking/pages/BookingPage.tsx
@@ -83,6 +83,7 @@ type BookingFormValues = {
   customInputs?: {
     [key: string]: string | boolean;
   };
+  rescheduleReason?: string;
 };
 
 const BookingPage = ({
@@ -255,6 +256,7 @@ const BookingPage = ({
       email: primaryAttendee.email || "",
       guests: guestListEmails,
       notes: booking.description || "",
+      rescheduleReason: "",
       customInputs: eventType.customInputs.reduce(
         (customInputs, input) => ({
           ...customInputs,
@@ -786,18 +788,31 @@ const BookingPage = ({
                     <label
                       htmlFor="notes"
                       className="mb-1 block text-sm font-medium text-gray-700 dark:text-white">
-                      {t("additional_notes")}
+                      {rescheduleUid ? t("reschedule_optional") : t("additional_notes")}
                     </label>
-                    <textarea
-                      {...bookingForm.register("notes")}
-                      id="notes"
-                      name="notes"
-                      rows={3}
-                      className={inputClassName}
-                      placeholder={t("share_additional_notes")}
-                      disabled={disabledExceptForOwner}
-                    />
+                    {rescheduleUid ? (
+                      <textarea
+                        {...bookingForm.register("rescheduleReason")}
+                        id="rescheduleReason"
+                        name="rescheduleReason"
+                        rows={3}
+                        className={inputClassName}
+                        placeholder={t("reschedule_placeholder")}
+                        disabled={disabledExceptForOwner}
+                      />
+                    ) : (
+                      <textarea
+                        {...bookingForm.register("notes")}
+                        id="notes"
+                        name="notes"
+                        rows={3}
+                        className={inputClassName}
+                        placeholder={t("share_additional_notes")}
+                        disabled={disabledExceptForOwner}
+                      />
+                    )}
                   </div>
+
                   <div className="flex items-start space-x-2 rtl:space-x-reverse">
                     <Button
                       type="submit"
diff --git a/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts b/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts
index 1a6ec58d74..58a5c9e553 100644
--- a/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts
+++ b/apps/web/lib/emails/templates/attendee-request-reschedule-email.ts
@@ -102,6 +102,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_attendee"
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle", {
   organizer: this.calEvent.organizer.name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getAdditionalNotes()}
@@ -151,6 +152,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}    
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/apps/web/lib/emails/templates/attendee-rescheduled-email.ts b/apps/web/lib/emails/templates/attendee-rescheduled-email.ts
index 804b81ce3f..1ad39fec14 100644
--- a/apps/web/lib/emails/templates/attendee-rescheduled-email.ts
+++ b/apps/web/lib/emails/templates/attendee-rescheduled-email.ts
@@ -52,6 +52,7 @@ export default class AttendeeRescheduledEmail extends AttendeeScheduledEmail {
       return `
   ${this.attendee.language.translate("event_has_been_rescheduled")}
   ${this.attendee.language.translate("emailed_you_and_any_other_attendees")}
+  ${this.calEvent.cancellationReason && this.getReason()}
   ${this.getWhat()}
   ${this.getWhen()}
   ${this.getLocation()}
@@ -112,6 +113,7 @@ ${this.getCustomInputs()}
                         <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;line-height:1;text-align:left;color:#3E3E3E;">
+                              ${this.calEvent.cancellationReason && this.getReason()}  
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/apps/web/lib/emails/templates/attendee-scheduled-email.ts b/apps/web/lib/emails/templates/attendee-scheduled-email.ts
index a791a00573..68671b275d 100644
--- a/apps/web/lib/emails/templates/attendee-scheduled-email.ts
+++ b/apps/web/lib/emails/templates/attendee-scheduled-email.ts
@@ -452,4 +452,12 @@ ${getRichDescription(this.calEvent)}
   protected getInviteeEnd(): Dayjs {
     return dayjs(this.calEvent.endTime).tz(this.getTimezone());
   }
+
+  protected getReason(): string {
+    return `
+    <div style="line-height: 6px; margin-bottom: 24px;">
+      <p style="color: #494949;">${this.calEvent.attendees[0].language.translate("reschedule_reason")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;">${this.calEvent.cancellationReason}</p>
+    </div>`;
+  }
 }
diff --git a/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts b/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts
index 76671fda18..b6251456b2 100644
--- a/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts
+++ b/apps/web/lib/emails/templates/organizer-request-reschedule-email.ts
@@ -111,6 +111,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_organizer
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle_organizer", {
   attendee: this.calEvent.attendees[0].name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getLocation()}
@@ -163,6 +164,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}    
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/apps/web/lib/emails/templates/organizer-rescheduled-email.ts b/apps/web/lib/emails/templates/organizer-rescheduled-email.ts
index 6dd315225a..6f33489d5c 100644
--- a/apps/web/lib/emails/templates/organizer-rescheduled-email.ts
+++ b/apps/web/lib/emails/templates/organizer-rescheduled-email.ts
@@ -59,6 +59,7 @@ export default class OrganizerRescheduledEmail extends OrganizerScheduledEmail {
     return `
 ${this.calEvent.organizer.language.translate("event_has_been_rescheduled")}
 ${this.calEvent.organizer.language.translate("emailed_you_and_any_other_attendees")}
+${this.calEvent.cancellationReason && this.getReason()}  
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getLocation()}
@@ -108,6 +109,7 @@ ${getCancelLink(this.calEvent)}
                         <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;line-height:1;text-align:left;color:#3E3E3E;">
+                              ${this.calEvent.cancellationReason && this.getReason()}    
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/apps/web/lib/emails/templates/organizer-scheduled-email.ts b/apps/web/lib/emails/templates/organizer-scheduled-email.ts
index 5059e58872..a6f251c0ee 100644
--- a/apps/web/lib/emails/templates/organizer-scheduled-email.ts
+++ b/apps/web/lib/emails/templates/organizer-scheduled-email.ts
@@ -439,4 +439,12 @@ ${getRichDescription(this.calEvent)}
   protected getOrganizerEnd(): Dayjs {
     return dayjs(this.calEvent.endTime).tz(this.getTimezone());
   }
+
+  protected getReason(): string {
+    return `
+    <div style="line-height: 6px; margin-bottom: 24px;">
+      <p style="color: #494949;">${this.calEvent.attendees[0].language.translate("reschedule_reason")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;">${this.calEvent.cancellationReason}</p>
+    </div>`;
+  }
 }
diff --git a/apps/web/pages/api/book/event.ts b/apps/web/pages/api/book/event.ts
index 06f4bc3509..ced0f6ba61 100644
--- a/apps/web/pages/api/book/event.ts
+++ b/apps/web/pages/api/book/event.ts
@@ -201,7 +201,11 @@ const getEventTypesFromDB = async (eventTypeId: number) => {
 
 type User = Prisma.UserGetPayload<typeof userSelect>;
 
-type ExtendedBookingCreateBody = BookingCreateBody & { noEmail?: boolean; recurringCount?: number };
+type ExtendedBookingCreateBody = BookingCreateBody & {
+  noEmail?: boolean;
+  recurringCount?: number;
+  rescheduleReason?: string;
+};
 
 export default async function handler(req: NextApiRequest, res: NextApiResponse) {
   const { recurringCount, noEmail, ...reqBody } = req.body as ExtendedBookingCreateBody;
@@ -677,11 +681,18 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
 
   if (originalRescheduledBooking?.uid) {
     // Use EventManager to conditionally use all needed integrations.
-    const updateManager = await eventManager.update(evt, originalRescheduledBooking.uid, booking?.id);
+    const updateManager = await eventManager.update(
+      evt,
+      originalRescheduledBooking.uid,
+      booking?.id,
+      reqBody.rescheduleReason
+    );
     // 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;
 
+    console.log("🚀 ~ file: event.ts ~ line 684 ~ handler ~ descripiton", reqBody);
+
     results = updateManager.results;
     referencesToCreate = updateManager.referencesToCreate;
     if (results.length > 0 && results.some((res) => !res.success)) {
@@ -711,7 +722,8 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
           {
             ...evt,
             additionInformation: metadata,
-            additionalNotes, // Resets back to the addtionalNote input and not the overriden value
+            additionalNotes, // Resets back to the additionalNote input and not the override value
+            cancellationReason: reqBody.rescheduleReason,
           },
           reqBody.recurringEventId ? (eventType.recurringEvent as RecurringEvent) : {}
         );
diff --git a/apps/web/playwright/reschedule.test.ts b/apps/web/playwright/reschedule.test.ts
index ec108b2d05..15ef383890 100644
--- a/apps/web/playwright/reschedule.test.ts
+++ b/apps/web/playwright/reschedule.test.ts
@@ -87,7 +87,7 @@ test.describe("Reschedule Tests", async () => {
 
     await expect(page.locator('[name="name"]')).toBeDisabled();
     await expect(page.locator('[name="email"]')).toBeDisabled();
-    await expect(page.locator('[name="notes"]')).toBeDisabled();
+    await expect(page.locator('[name="rescheduleReason"]')).toBeDisabled();
 
     await page.locator('[data-testid="confirm-reschedule-button"]').click();
 
diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index 516cae00d9..e816e4264a 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -868,6 +868,8 @@
   "go_to": "Go to: ",
   "zapier_invite_link": "Zapier Invite Link",
   "meeting_url_provided_after_confirmed":"A Meeting URL will be created once the event is confirmed.",
+  "reschedule_optional": "Reason for rescheduling (optional)",
+  "reschedule_placeholder": "Let others know why you need to reschedule",
   "event_cancelled":"This event is cancelled",
   "emailed_information_about_cancelled_event": "We emailed you and the other attendees to let them know.",
   "this_input_will_shown_booking_this_event": "This input will be shown when booking this event",
diff --git a/packages/app-store/vital/lib/templates/attendee-request-reschedule-email.ts b/packages/app-store/vital/lib/templates/attendee-request-reschedule-email.ts
index 6052ef19c4..a032a37be8 100644
--- a/packages/app-store/vital/lib/templates/attendee-request-reschedule-email.ts
+++ b/packages/app-store/vital/lib/templates/attendee-request-reschedule-email.ts
@@ -102,6 +102,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_attendee"
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle", {
   organizer: this.calEvent.organizer.name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}   
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getAdditionalNotes()}
@@ -150,6 +151,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}    
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/packages/app-store/vital/lib/templates/base-template.ts b/packages/app-store/vital/lib/templates/base-template.ts
index cf0479bcf8..3b8b164463 100644
--- a/packages/app-store/vital/lib/templates/base-template.ts
+++ b/packages/app-store/vital/lib/templates/base-template.ts
@@ -406,4 +406,12 @@ ${getRichDescription(this.calEvent)}
   protected getOrganizerEnd(): Dayjs {
     return dayjs(this.calEvent.endTime).tz(this.getTimezone());
   }
+
+  protected getReason(): string {
+    return `
+    <div style="line-height: 6px; margin-bottom: 24px;">
+      <p style="color: #494949;">${this.calEvent.attendees[0].language.translate("reschedule_reason")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;">${this.calEvent.cancellationReason}</p>
+    </div>`;
+  }
 }
diff --git a/packages/app-store/vital/lib/templates/organizer-request-reschedule-email.ts b/packages/app-store/vital/lib/templates/organizer-request-reschedule-email.ts
index 716d47d3d1..2c5a9a56e1 100644
--- a/packages/app-store/vital/lib/templates/organizer-request-reschedule-email.ts
+++ b/packages/app-store/vital/lib/templates/organizer-request-reschedule-email.ts
@@ -111,6 +111,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_organizer
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle_organizer", {
   attendee: this.calEvent.attendees[0].name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getLocation()}
@@ -162,6 +163,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}   
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/packages/app-store/wipemycalother/lib/templates/attendee-request-reschedule-email.ts b/packages/app-store/wipemycalother/lib/templates/attendee-request-reschedule-email.ts
index 6052ef19c4..a032a37be8 100644
--- a/packages/app-store/wipemycalother/lib/templates/attendee-request-reschedule-email.ts
+++ b/packages/app-store/wipemycalother/lib/templates/attendee-request-reschedule-email.ts
@@ -102,6 +102,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_attendee"
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle", {
   organizer: this.calEvent.organizer.name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}   
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getAdditionalNotes()}
@@ -150,6 +151,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}    
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/packages/app-store/wipemycalother/lib/templates/base-template.ts b/packages/app-store/wipemycalother/lib/templates/base-template.ts
index fe48304c72..244804b48e 100644
--- a/packages/app-store/wipemycalother/lib/templates/base-template.ts
+++ b/packages/app-store/wipemycalother/lib/templates/base-template.ts
@@ -406,4 +406,12 @@ ${getRichDescription(this.calEvent)}
   protected getOrganizerEnd(): Dayjs {
     return dayjs(this.calEvent.endTime).tz(this.getTimezone());
   }
+
+  protected getReason(): string {
+    return `
+    <div style="line-height: 6px; margin-bottom: 24px;">
+      <p style="color: #494949;">${this.calEvent.attendees[0].language.translate("reschedule_reason")}</p>
+      <p style="color: #494949; font-weight: 400; line-height: 24px;">${this.calEvent.cancellationReason}</p>
+    </div>`;
+  }
 }
diff --git a/packages/app-store/wipemycalother/lib/templates/organizer-request-reschedule-email.ts b/packages/app-store/wipemycalother/lib/templates/organizer-request-reschedule-email.ts
index 716d47d3d1..c79f335014 100644
--- a/packages/app-store/wipemycalother/lib/templates/organizer-request-reschedule-email.ts
+++ b/packages/app-store/wipemycalother/lib/templates/organizer-request-reschedule-email.ts
@@ -111,6 +111,7 @@ ${this.calEvent.organizer.language.translate("request_reschedule_title_organizer
 ${this.calEvent.organizer.language.translate("request_reschedule_subtitle_organizer", {
   attendee: this.calEvent.attendees[0].name,
 })},
+${this.calEvent.cancellationReason && this.getReason()}   
 ${this.getWhat()}
 ${this.getWhen()}
 ${this.getLocation()}
@@ -162,6 +163,7 @@ ${getCancelLink(this.calEvent)}
                         <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.calEvent.cancellationReason && this.getReason()}   
                               ${this.getWhat()}
                               ${this.getWhen()}
                               ${this.getWho()}
diff --git a/packages/core/EventManager.ts b/packages/core/EventManager.ts
index 27adf6fa56..9f0c89fc7d 100644
--- a/packages/core/EventManager.ts
+++ b/packages/core/EventManager.ts
@@ -165,7 +165,8 @@ export default class EventManager {
   public async update(
     event: CalendarEvent,
     rescheduleUid: string,
-    newBookingId?: number
+    newBookingId?: number,
+    rescheduleReason?: string
   ): Promise<CreateUpdateResult> {
     const evt = processLocation(event);
 
@@ -201,6 +202,16 @@ export default class EventManager {
       throw new Error("booking not found");
     }
 
+    // Add reschedule reason to new booking
+    await prisma.booking.update({
+      where: {
+        id: newBookingId,
+      },
+      data: {
+        cancellationReason: rescheduleReason,
+      },
+    });
+
     const isDedicated = evt.location ? isDedicatedIntegration(evt.location) : null;
     const results: Array<EventResult> = [];
     // If and only if event type is a dedicated meeting, update the dedicated video meeting.