diff --git a/packages/lib/server/service/BookingWebhookFactory.ts b/packages/lib/server/service/BookingWebhookFactory.ts
new file mode 100644
index 0000000000..44141099a7
--- /dev/null
+++ b/packages/lib/server/service/BookingWebhookFactory.ts
@@ -0,0 +1,127 @@
+import type { Person } from "@calcom/types/Calendar";
+import type { JsonValue } from "@calcom/types/JsonObject";
+
+function isObjectButNotArray(obj: unknown): obj is Record<string, unknown> {
+  return typeof obj === "object" && !Array.isArray(obj);
+}
+
+type DestinationCalendar = {
+  id: number;
+  integration: string;
+  externalId: string;
+  primaryEmail: string | null;
+  userId: number | null;
+  eventTypeId: number | null;
+  credentialId: number | null;
+  createdAt: Date | null;
+  updatedAt: Date | null;
+  delegationCredentialId: string | null;
+  domainWideDelegationCredentialId: string | null;
+};
+
+type Response = {
+  label: string;
+  value: string | boolean | string[] | { value: string; optionValue: string } | Record<string, string>;
+  isHidden?: boolean | undefined;
+};
+
+interface BaseWebhookPayload {
+  bookingId: number;
+  title: string;
+  eventSlug: string | null;
+  description: string | null;
+  customInputs: JsonValue | null;
+  responses: Record<string, Response>;
+  userFieldsResponses: Record<string, Response>;
+  startTime: string;
+  endTime: string;
+  organizer: Person;
+  attendees: Person[];
+  uid: string;
+  location: string | null;
+  destinationCalendar: DestinationCalendar | null;
+  cancellationReason: string | null;
+  iCalUID: string | null;
+  smsReminderNumber?: string;
+  cancelledBy: string | null;
+}
+
+interface CancelledEventPayload extends BaseWebhookPayload {
+  cancelledBy: string;
+  cancellationReason: string;
+}
+
+export class BookingWebhookFactory {
+  private getType(params: BaseWebhookPayload) {
+    return params.eventSlug || params.title || "";
+  }
+
+  private getTitle(params: BaseWebhookPayload) {
+    return params.title || "";
+  }
+
+  private getDestinationCalendar(params: BaseWebhookPayload) {
+    return params.destinationCalendar ? [params.destinationCalendar] : [];
+  }
+
+  private getCustomInputs(params: BaseWebhookPayload) {
+    return isObjectButNotArray(params.customInputs) ? params.customInputs : undefined;
+  }
+
+  /**
+   * Creates base webhook payload with common fields
+   */
+  private createBasePayload(params: BaseWebhookPayload) {
+    const {
+      bookingId,
+      title,
+      eventSlug,
+      description,
+      customInputs,
+      startTime,
+      endTime,
+      uid,
+      location,
+      organizer,
+      attendees,
+      responses,
+      userFieldsResponses,
+      destinationCalendar,
+      smsReminderNumber,
+      iCalUID,
+    } = params;
+
+    const basePayload = {
+      bookingId,
+      type: this.getType(params),
+      title: this.getTitle(params),
+      description,
+      customInputs: this.getCustomInputs(params),
+      responses,
+      userFieldsResponses,
+      startTime,
+      endTime,
+      organizer,
+      attendees,
+      uid,
+      location,
+      destinationCalendar: this.getDestinationCalendar(params),
+      iCalUID,
+      smsReminderNumber,
+    };
+
+    return basePayload;
+  }
+
+  public createCancelledEventPayload(params: CancelledEventPayload) {
+    const basePayload = this.createBasePayload({
+      ...params,
+    });
+
+    return {
+      ...basePayload,
+      cancelledBy: params.cancelledBy,
+      cancellationReason: params.cancellationReason,
+    };
+  }
+}
diff --git a/packages/lib/server/service/__tests__/BookingWebhookFactory.test.ts b/packages/lib/server/service/__tests__/BookingWebhookFactory.test.ts
new file mode 100644
index 0000000000..11da828849
--- /dev/null
+++ b/packages/lib/server/service/__tests__/BookingWebhookFactory.test.ts
@@ -0,0 +1,318 @@
+import { describe, it, expect } from "vitest";
+
+import type { Person } from "@calcom/types/Calendar";
+
+import { BookingWebhookFactory } from "../BookingWebhookFactory";
+
+const createTestOrganizer = (overrides?: Partial<Person>): Person => ({
+  email: "organizer@example.com",
+  name: "Test Organizer",
+  timeZone: "UTC",
+  language: { locale: "en", translate: (() => "") as any },
+  ...overrides,
+});
+
+const createTestAttendee = (overrides?: Partial<Person>): Person => ({
+  email: "attendee@example.com",
+  name: "Test Attendee",
+  timeZone: "UTC",
+  language: { locale: "en", translate: (() => "") as any },
+  ...overrides,
+});
+
+const createTestBooking = (overrides?: Record<string, any>) => ({
+  id: 12345,
+  uid: "test-uid-123",
+  title: "Test Event",
+  description: "Test Description",
+  startTime: new Date("2025-01-24T10:00:00Z"),
+  endTime: new Date("2025-01-24T11:00:00Z"),
+  location: "https://meet.example.com",
+  customInputs: { field1: "value1" },
+  responses: { name: { value: "Test User" } },
+  userFieldsResponses: { company: { value: "Test Corp" } },
+  smsReminderNumber: "+1234567890",
+  iCalUID: "ical-uid-123",
+  ...overrides,
+});
+
+describe("BookingWebhookFactory", () => {
+  describe("createCancelledEventPayload", () => {
+    it("should create a basic cancelled event payload with required fields", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+      const organizer = createTestOrganizer();
+      const attendees = [createTestAttendee()];
+
+      const payload = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: booking.title,
+        eventSlug: "test-event",
+        description: booking.description,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: booking.location,
+        customInputs: booking.customInputs,
+        responses: booking.responses,
+        userFieldsResponses: booking.userFieldsResponses,
+        smsReminderNumber: booking.smsReminderNumber,
+        iCalUID: booking.iCalUID,
+        organizer,
+        attendees,
+        destinationCalendar: null,
+        cancelledBy: "test@example.com",
+        cancellationReason: "User requested",
+      });
+
+      expect(payload.bookingId).toBe(12345);
+      expect(payload.uid).toBe("test-uid-123");
+      expect(payload.title).toBe("Test Event");
+      expect(payload.description).toBe("Test Description");
+      expect(payload.organizer).toEqual(organizer);
+      expect(payload.attendees).toEqual(attendees);
+      expect(payload.type).toBe("test-event");
+      expect(payload.startTime).toBe(booking.startTime.toISOString());
+      expect(payload.endTime).toBe(booking.endTime.toISOString());
+      expect(payload.location).toBe("https://meet.example.com");
+      expect(payload.customInputs).toEqual({ field1: "value1" });
+      expect(payload.responses).toEqual({ name: { value: "Test User" } });
+      expect(payload.userFieldsResponses).toEqual({ company: { value: "Test Corp" } });
+      expect(payload.smsReminderNumber).toBe("+1234567890");
+      expect(payload.iCalUID).toBe("ical-uid-123");
+      expect(payload.destinationCalendar).toEqual([]);
+      expect(payload.cancellationReason).toBe("User requested");
+      expect(payload.cancelledBy).toBe("test@example.com");
+
+      // Verify no extra properties exist
+      const expectedKeys = [
+        "bookingId",
+        "type",
+        "title",
+        "description",
+        "customInputs",
+        "responses",
+        "userFieldsResponses",
+        "startTime",
+        "endTime",
+        "organizer",
+        "attendees",
+        "uid",
+        "location",
+        "destinationCalendar",
+        "iCalUID",
+        "smsReminderNumber",
+        "cancellationReason",
+        "cancelledBy",
+      ];
+      const actualKeys = Object.keys(payload).sort();
+      expect(actualKeys).toEqual(expectedKeys.sort());
+    });
+
+    it("should handle responses and userFieldsResponses", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+      const responses = { field1: "response1", field2: "response2" };
+      const userFieldsResponses = { company: "Test Corp", department: "Engineering" };
+
+      const payload = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: booking.title,
+        eventSlug: null,
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses,
+        userFieldsResponses,
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [createTestAttendee()],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payload.responses).toEqual(responses);
+      expect(payload.userFieldsResponses).toEqual(userFieldsResponses);
+    });
+
+    it("should handle destination calendar as single object", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+      const destinationCalendar = {
+        id: 1,
+        integration: "google",
+        externalId: "cal123",
+        primaryEmail: null,
+        userId: null,
+        eventTypeId: null,
+        credentialId: null,
+        createdAt: null,
+        updatedAt: null,
+        delegationCredentialId: null,
+        domainWideDelegationCredentialId: null,
+      };
+
+      const payload = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: booking.title,
+        eventSlug: null,
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payload.destinationCalendar).toEqual([destinationCalendar]);
+    });
+
+    it("should handle null destination calendar", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+
+      const payload = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: booking.title,
+        eventSlug: null,
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payload.destinationCalendar).toEqual([]);
+    });
+
+    it("should handle sms reminder number and iCal UID", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+
+      const payload = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: booking.title,
+        eventSlug: null,
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: "+1234567890",
+        iCalUID: "ical-uid-123",
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payload.smsReminderNumber).toBe("+1234567890");
+      expect(payload.iCalUID).toBe("ical-uid-123");
+    });
+
+    it("should derive type from eventSlug when available, otherwise from title", () => {
+      const factory = new BookingWebhookFactory();
+      const booking = createTestBooking();
+
+      // Test with eventSlug provided
+      const payloadWithSlug = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: "Meeting Title",
+        eventSlug: "team-standup",
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payloadWithSlug.type).toBe("team-standup");
+
+      // Test with eventSlug null, should use title
+      const payloadWithoutSlug = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: "Meeting Title",
+        eventSlug: null,
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payloadWithoutSlug.type).toBe("Meeting Title");
+
+      // Test with both eventSlug and title empty
+      const payloadEmpty = factory.createCancelledEventPayload({
+        bookingId: booking.id,
+        uid: booking.uid,
+        title: "",
+        eventSlug: "",
+        description: null,
+        startTime: booking.startTime.toISOString(),
+        endTime: booking.endTime.toISOString(),
+        location: null,
+        customInputs: null,
+        responses: {},
+        userFieldsResponses: {},
+        smsReminderNumber: null,
+        iCalUID: null,
+        organizer: createTestOrganizer(),
+        attendees: [],
+        destinationCalendar: null,
+        cancelledBy: "user@example.com",
+        cancellationReason: "Test",
+      });
+
+      expect(payloadEmpty.type).toBe("");
+    });
+  });
+});
diff --git a/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts b/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
index 32d8216ea3..9911b5e6f4 100644
--- a/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
+++ b/packages/trpc/server/routers/viewer/bookings/requestReschedule.handler.ts
@@ -14,18 +14,18 @@ import { getDelegationCredentialOrRegularCredential } from "@calcom/lib/delegati
 import { getBookerBaseUrl } from "@calcom/lib/getBookerUrl/server";
 import getOrgIdFromMemberOrTeamId from "@calcom/lib/getOrgIdFromMemberOrTeamId";
 import { getTeamIdFromEventType } from "@calcom/lib/getTeamIdFromEventType";
-import { isPrismaObjOrUndefined } from "@calcom/lib/isPrismaObj";
 import logger from "@calcom/lib/logger";
 import { safeStringify } from "@calcom/lib/safeStringify";
 import { getUsersCredentialsIncludeServiceAccountKey } from "@calcom/lib/server/getUsersCredentials";
 import { getTranslation } from "@calcom/lib/server/i18n";
 import { WorkflowRepository } from "@calcom/lib/server/repository/workflow";
+import { BookingWebhookFactory } from "@calcom/lib/server/service/BookingWebhookFactory";
 import { deleteMeeting } from "@calcom/lib/videoClient";
 import { prisma } from "@calcom/prisma";
 import type { WebhookTriggerEvents } from "@calcom/prisma/enums";
 import { BookingStatus } from "@calcom/prisma/enums";
 import type { EventTypeMetadata } from "@calcom/prisma/zod-utils";
-import type { CalendarEvent, Person } from "@calcom/types/Calendar";
+import type { Person } from "@calcom/types/Calendar";
 
 import { TRPCError } from "@trpc/server";
 
@@ -109,7 +109,7 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
 
   if (bookingBelongsToTeam && bookingToReschedule.eventType?.teamId) {
     const userTeamIds = userTeams.teams.map((item) => item.teamId);
-    if (userTeamIds.indexOf(bookingToReschedule?.eventType?.teamId) === -1) {
+    if (userTeamIds.indexOf(bookingToReschedule.eventType?.teamId) === -1) {
       throw new TRPCError({ code: "FORBIDDEN", message: "User isn't a member on the team" });
     }
     log.debug(
@@ -182,7 +182,7 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
   const [userAsPeopleType] = usersToPeopleType([user], userTranslation);
   const organizer = {
     ...userAsPeopleType,
-    email: bookingToReschedule?.userPrimaryEmail ?? userAsPeopleType.email,
+    email: bookingToReschedule.userPrimaryEmail ?? userAsPeopleType.email,
   };
 
   const builder = new CalendarEventBuilder();
@@ -276,31 +276,38 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
     eventType?.metadata as EventTypeMetadata
   );
 
-  const evt: CalendarEvent = {
-    title: bookingToReschedule?.title,
-    type: event && event.slug ? event.slug : bookingToReschedule.title,
-    description: bookingToReschedule?.description || "",
-    customInputs: isPrismaObjOrUndefined(bookingToReschedule.customInputs),
-    ...getCalEventResponses({
-      booking: bookingToReschedule,
-      bookingFields: bookingToReschedule.eventType?.bookingFields ?? null,
-    }),
-    startTime: bookingToReschedule?.startTime ? dayjs(bookingToReschedule.startTime).format() : "",
-    endTime: bookingToReschedule?.endTime ? dayjs(bookingToReschedule.endTime).format() : "",
+  const calEventResponses = getCalEventResponses({
+    booking: bookingToReschedule,
+    bookingFields: bookingToReschedule.eventType?.bookingFields ?? null,
+  });
+
+  const webhookFactory = new BookingWebhookFactory();
+  const payload = webhookFactory.createCancelledEventPayload({
+    bookingId: bookingToReschedule.id,
+    title: bookingToReschedule.title,
+    eventSlug: event.slug ?? null,
+    description: bookingToReschedule.description,
+    customInputs: bookingToReschedule.customInputs,
+    responses: calEventResponses.responses,
+    userFieldsResponses: calEventResponses.userFieldsResponses,
+    startTime: bookingToReschedule.startTime ? dayjs(bookingToReschedule.startTime).format() : "",
+    endTime: bookingToReschedule.endTime ? dayjs(bookingToReschedule.endTime).format() : "",
     organizer,
     attendees: usersToPeopleType(
       // username field doesn't exists on attendee but could be in the future
       bookingToReschedule.attendees as unknown as PersonAttendeeCommonFields[],
       tAttendees
     ),
-    uid: bookingToReschedule?.uid,
-    location: bookingToReschedule?.location,
-    destinationCalendar: bookingToReschedule?.destinationCalendar
-      ? [bookingToReschedule?.destinationCalendar]
-      : [],
+    uid: bookingToReschedule.uid,
+    location: bookingToReschedule.location,
+    destinationCalendar: bookingToReschedule.destinationCalendar,
     cancellationReason: `Please reschedule. ${cancellationReason}`, // TODO::Add i18-next for this
-    iCalUID: bookingToReschedule?.iCalUID,
-  };
+    iCalUID: bookingToReschedule.iCalUID,
+    ...(bookingToReschedule.smsReminderNumber && {
+      smsReminderNumber: bookingToReschedule.smsReminderNumber,
+    }),
+    cancelledBy: user.email,
+  });
 
   // Send webhook
   const eventTrigger: WebhookTriggerEvents = "BOOKING_CANCELLED";
@@ -308,7 +315,7 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
   const teamId = await getTeamIdFromEventType({
     eventType: {
       team: { id: bookingToReschedule.eventType?.teamId ?? null },
-      parentId: bookingToReschedule?.eventType?.parentId ?? null,
+      parentId: bookingToReschedule.eventType?.parentId ?? null,
     },
   });
 
@@ -327,13 +334,9 @@ export const requestRescheduleHandler = async ({ ctx, input }: RequestReschedule
   const webhooks = await getWebhooks(subscriberOptions);
 
   const promises = webhooks.map((webhook) =>
-    sendPayload(webhook.secret, eventTrigger, new Date().toISOString(), webhook, {
-      ...evt,
-      smsReminderNumber: bookingToReschedule.smsReminderNumber || undefined,
-      cancelledBy: user.email,
-    }).catch((e) => {
+    sendPayload(webhook.secret, eventTrigger, new Date().toISOString(), webhook, payload).catch((e) => {
       log.error(
-        `Error executing webhook for event: ${eventTrigger}, URL: ${webhook.subscriberUrl}, bookingId: ${evt.bookingId}, bookingUid: ${evt.uid}`,
+        `Error executing webhook for event: ${eventTrigger}, URL: ${webhook.subscriberUrl}, bookingId: ${payload.bookingId}, bookingUid: ${payload.uid}`,
         safeStringify(e)
       );
     })
diff --git a/packages/types/JsonObject.d.ts b/packages/types/JsonObject.d.ts
new file mode 100644
index 0000000000..2dfba36d47
--- /dev/null
+++ b/packages/types/JsonObject.d.ts
@@ -0,0 +1,6 @@
+/**
+ * Decouples the types from Prisma
+ */
+export type JsonValue = string | number | boolean | null | JsonObject | JsonArray;
+export type JsonArray = JsonValue[];
+export type JsonObject = { [Key in string]?: JsonValue };