diff --git a/apps/web/components/booking/BookingListItem.tsx b/apps/web/components/booking/BookingListItem.tsx
index 3dc01a2dcb..a8f80500ba 100644
--- a/apps/web/components/booking/BookingListItem.tsx
+++ b/apps/web/components/booking/BookingListItem.tsx
@@ -318,6 +318,7 @@ function BookingListItem(booking: BookingItemProps) {
             <DialogClose />
             <Button
               disabled={mutation.isLoading}
+              data-testid="rejection-confirm"
               onClick={() => {
                 bookingConfirm(false);
               }}>
diff --git a/apps/web/playwright/webhook.e2e.ts b/apps/web/playwright/webhook.e2e.ts
index 533dc93418..a0ed6e53c3 100644
--- a/apps/web/playwright/webhook.e2e.ts
+++ b/apps/web/playwright/webhook.e2e.ts
@@ -1,131 +1,387 @@
 import { expect } from "@playwright/test";
 
 import { test } from "./lib/fixtures";
-import { createHttpServer, selectFirstAvailableTimeSlotNextMonth, waitFor } from "./lib/testUtils";
+import {
+  bookOptinEvent,
+  createHttpServer,
+  selectFirstAvailableTimeSlotNextMonth,
+  waitFor,
+} from "./lib/testUtils";
 
 test.afterEach(({ users }) => users.deleteAll());
 
-test("add webhook & test that creating an event triggers a webhook call", async ({
-  page,
-  users,
-}, testInfo) => {
-  const webhookReceiver = createHttpServer();
-  const user = await users.create();
-  const [eventType] = user.eventTypes;
-  await user.login();
-  await page.goto(`/settings/developer/webhooks`);
+test.describe("BOOKING_CREATED", async () => {
+  test("add webhook & test that creating an event triggers a webhook call", async ({
+    page,
+    users,
+  }, testInfo) => {
+    const webhookReceiver = createHttpServer();
+    const user = await users.create();
+    const [eventType] = user.eventTypes;
+    await user.login();
+    await page.goto(`/settings/developer/webhooks`);
 
-  // --- add webhook
-  await page.click('[data-testid="new_webhook"]');
+    // --- add webhook
+    await page.click('[data-testid="new_webhook"]');
 
-  await page.fill('[name="subscriberUrl"]', webhookReceiver.url);
+    await page.fill('[name="subscriberUrl"]', webhookReceiver.url);
 
-  await page.fill('[name="secret"]', "secret");
+    await page.fill('[name="secret"]', "secret");
 
-  await Promise.all([
-    page.click("[type=submit]"),
-    page.waitForURL((url) => url.pathname.endsWith("/settings/developer/webhooks")),
-  ]);
+    await Promise.all([
+      page.click("[type=submit]"),
+      page.waitForURL((url) => url.pathname.endsWith("/settings/developer/webhooks")),
+    ]);
 
-  // page contains the url
-  expect(page.locator(`text='${webhookReceiver.url}'`)).toBeDefined();
+    // page contains the url
+    expect(page.locator(`text='${webhookReceiver.url}'`)).toBeDefined();
 
-  // --- Book the first available day next month in the pro user's "30min"-event
-  await page.goto(`/${user.username}/${eventType.slug}`);
-  await selectFirstAvailableTimeSlotNextMonth(page);
+    // --- Book the first available day next month in the pro user's "30min"-event
+    await page.goto(`/${user.username}/${eventType.slug}`);
+    await selectFirstAvailableTimeSlotNextMonth(page);
 
-  // --- fill form
-  await page.fill('[name="name"]', "Test Testson");
-  await page.fill('[name="email"]', "test@example.com");
-  await page.press('[name="email"]', "Enter");
+    // --- fill form
+    await page.fill('[name="name"]', "Test Testson");
+    await page.fill('[name="email"]', "test@example.com");
+    await page.press('[name="email"]', "Enter");
 
-  // --- check that webhook was called
-  await waitFor(() => {
-    expect(webhookReceiver.requestList.length).toBe(1);
-  });
+    // --- check that webhook was called
+    await waitFor(() => {
+      expect(webhookReceiver.requestList.length).toBe(1);
+    });
 
-  const [request] = webhookReceiver.requestList;
-  const body = request.body as any;
+    const [request] = webhookReceiver.requestList;
+    const body = request.body as any;
 
-  // remove dynamic properties that differs depending on where you run the tests
-  const dynamic = "[redacted/dynamic]";
-  body.createdAt = dynamic;
-  body.payload.startTime = dynamic;
-  body.payload.endTime = dynamic;
-  body.payload.location = dynamic;
-  for (const attendee of body.payload.attendees) {
-    attendee.timeZone = dynamic;
-    attendee.language = dynamic;
-  }
-  body.payload.organizer.id = dynamic;
-  body.payload.organizer.email = dynamic;
-  body.payload.organizer.timeZone = dynamic;
-  body.payload.organizer.language = dynamic;
-  body.payload.uid = dynamic;
-  body.payload.bookingId = dynamic;
-  body.payload.additionalInformation = dynamic;
-  body.payload.requiresConfirmation = dynamic;
-  body.payload.eventTypeId = dynamic;
-  body.payload.videoCallData = dynamic;
-  body.payload.appsStatus = dynamic;
-  body.payload.metadata.videoCallUrl = dynamic;
+    // remove dynamic properties that differs depending on where you run the tests
+    const dynamic = "[redacted/dynamic]";
+    body.createdAt = dynamic;
+    body.payload.startTime = dynamic;
+    body.payload.endTime = dynamic;
+    body.payload.location = dynamic;
+    for (const attendee of body.payload.attendees) {
+      attendee.timeZone = dynamic;
+      attendee.language = dynamic;
+    }
+    body.payload.organizer.id = dynamic;
+    body.payload.organizer.email = dynamic;
+    body.payload.organizer.timeZone = dynamic;
+    body.payload.organizer.language = dynamic;
+    body.payload.uid = dynamic;
+    body.payload.bookingId = dynamic;
+    body.payload.additionalInformation = dynamic;
+    body.payload.requiresConfirmation = dynamic;
+    body.payload.eventTypeId = dynamic;
+    body.payload.videoCallData = dynamic;
+    body.payload.appsStatus = dynamic;
+    body.payload.metadata.videoCallUrl = dynamic;
 
-  expect(body).toMatchObject({
-    triggerEvent: "BOOKING_CREATED",
-    createdAt: "[redacted/dynamic]",
-    payload: {
-      type: "30 min",
-      title: "30 min between Nameless and Test Testson",
-      description: "",
-      additionalNotes: "",
-      customInputs: {},
-      startTime: "[redacted/dynamic]",
-      endTime: "[redacted/dynamic]",
-      organizer: {
-        id: "[redacted/dynamic]",
-        name: "Nameless",
-        email: "[redacted/dynamic]",
-        timeZone: "[redacted/dynamic]",
-        language: "[redacted/dynamic]",
-      },
-      responses: {
-        email: {
-          value: "test@example.com",
-          label: "email_address",
-        },
-        name: {
-          value: "Test Testson",
-          label: "your_name",
-        },
-      },
-      userFieldsResponses: {},
-      attendees: [
-        {
-          email: "test@example.com",
-          name: "Test Testson",
+    expect(body).toMatchObject({
+      triggerEvent: "BOOKING_CREATED",
+      createdAt: "[redacted/dynamic]",
+      payload: {
+        type: "30 min",
+        title: "30 min between Nameless and Test Testson",
+        description: "",
+        additionalNotes: "",
+        customInputs: {},
+        startTime: "[redacted/dynamic]",
+        endTime: "[redacted/dynamic]",
+        organizer: {
+          id: "[redacted/dynamic]",
+          name: "Nameless",
+          email: "[redacted/dynamic]",
           timeZone: "[redacted/dynamic]",
           language: "[redacted/dynamic]",
         },
-      ],
-      location: "[redacted/dynamic]",
-      destinationCalendar: null,
-      hideCalendarNotes: false,
-      requiresConfirmation: "[redacted/dynamic]",
-      eventTypeId: "[redacted/dynamic]",
-      seatsShowAttendees: true,
-      seatsPerTimeSlot: null,
-      uid: "[redacted/dynamic]",
-      eventTitle: "30 min",
-      eventDescription: null,
-      price: 0,
-      currency: "usd",
-      length: 30,
-      bookingId: "[redacted/dynamic]",
-      metadata: { videoCallUrl: "[redacted/dynamic]" },
-      status: "ACCEPTED",
-      additionalInformation: "[redacted/dynamic]",
-    },
-  });
+        responses: {
+          email: {
+            value: "test@example.com",
+            label: "email_address",
+          },
+          name: {
+            value: "Test Testson",
+            label: "your_name",
+          },
+        },
+        userFieldsResponses: {},
+        attendees: [
+          {
+            email: "test@example.com",
+            name: "Test Testson",
+            timeZone: "[redacted/dynamic]",
+            language: "[redacted/dynamic]",
+          },
+        ],
+        location: "[redacted/dynamic]",
+        destinationCalendar: null,
+        hideCalendarNotes: false,
+        requiresConfirmation: "[redacted/dynamic]",
+        eventTypeId: "[redacted/dynamic]",
+        seatsShowAttendees: true,
+        seatsPerTimeSlot: null,
+        uid: "[redacted/dynamic]",
+        eventTitle: "30 min",
+        eventDescription: null,
+        price: 0,
+        currency: "usd",
+        length: 30,
+        bookingId: "[redacted/dynamic]",
+        metadata: { videoCallUrl: "[redacted/dynamic]" },
+        status: "ACCEPTED",
+        additionalInformation: "[redacted/dynamic]",
+      },
+    });
 
-  webhookReceiver.close();
+    webhookReceiver.close();
+  });
+});
+
+test.describe("BOOKING_REJECTED", async () => {
+  test("can book an event that requires confirmation and then that booking can be rejected by organizer", async ({
+    page,
+    users,
+  }) => {
+    const webhookReceiver = createHttpServer();
+    // --- create a user
+    const user = await users.create();
+
+    // --- visit user page
+    await page.goto(`/${user.username}`);
+
+    // --- book the user's event
+    await bookOptinEvent(page);
+
+    // --- login as that user
+    await user.login();
+
+    await page.goto(`/settings/developer/webhooks`);
+
+    // --- add webhook
+    await page.click('[data-testid="new_webhook"]');
+
+    await page.fill('[name="subscriberUrl"]', webhookReceiver.url);
+
+    await page.fill('[name="secret"]', "secret");
+
+    await Promise.all([
+      page.click("[type=submit]"),
+      page.waitForURL((url) => url.pathname.endsWith("/settings/developer/webhooks")),
+    ]);
+
+    // page contains the url
+    expect(page.locator(`text='${webhookReceiver.url}'`)).toBeDefined();
+
+    await page.goto("/bookings/unconfirmed");
+    await page.click('[data-testid="reject"]');
+    await page.click('[data-testid="rejection-confirm"]');
+    await page.waitForResponse((response) => response.url().includes("/api/trpc/bookings/confirm"));
+
+    // --- check that webhook was called
+    await waitFor(() => {
+      expect(webhookReceiver.requestList.length).toBe(1);
+    });
+    const [request] = webhookReceiver.requestList;
+    const body = request.body as any;
+
+    // remove dynamic properties that differs depending on where you run the tests
+    const dynamic = "[redacted/dynamic]";
+    body.createdAt = dynamic;
+    body.payload.startTime = dynamic;
+    body.payload.endTime = dynamic;
+    body.payload.location = dynamic;
+    for (const attendee of body.payload.attendees) {
+      attendee.timeZone = dynamic;
+      attendee.language = dynamic;
+    }
+    body.payload.organizer.id = dynamic;
+    body.payload.organizer.email = dynamic;
+    body.payload.organizer.timeZone = dynamic;
+    body.payload.organizer.language = dynamic;
+    body.payload.uid = dynamic;
+    body.payload.bookingId = dynamic;
+    body.payload.additionalInformation = dynamic;
+    body.payload.requiresConfirmation = dynamic;
+    body.payload.eventTypeId = dynamic;
+    body.payload.videoCallData = dynamic;
+    body.payload.appsStatus = dynamic;
+    // body.payload.metadata.videoCallUrl = dynamic;
+
+    expect(body).toMatchObject({
+      triggerEvent: "BOOKING_REJECTED",
+      createdAt: "[redacted/dynamic]",
+      payload: {
+        type: "Opt in",
+        title: "Opt in between Nameless and Test Testson",
+        customInputs: {},
+        startTime: "[redacted/dynamic]",
+        endTime: "[redacted/dynamic]",
+        organizer: {
+          id: "[redacted/dynamic]",
+          name: "Unnamed",
+          email: "[redacted/dynamic]",
+          timeZone: "[redacted/dynamic]",
+          language: "[redacted/dynamic]",
+        },
+        responses: {
+          email: {
+            value: "test@example.com",
+            label: "email",
+          },
+          name: {
+            value: "Test Testson",
+            label: "name",
+          },
+        },
+        userFieldsResponses: {},
+        attendees: [
+          {
+            email: "test@example.com",
+            name: "Test Testson",
+            timeZone: "[redacted/dynamic]",
+            language: "[redacted/dynamic]",
+          },
+        ],
+        location: "[redacted/dynamic]",
+        destinationCalendar: null,
+        // hideCalendarNotes: false,
+        requiresConfirmation: "[redacted/dynamic]",
+        eventTypeId: "[redacted/dynamic]",
+        uid: "[redacted/dynamic]",
+        eventTitle: "Opt in",
+        eventDescription: null,
+        price: 0,
+        currency: "usd",
+        length: 30,
+        bookingId: "[redacted/dynamic]",
+        // metadata: { videoCallUrl: "[redacted/dynamic]" },
+        status: "REJECTED",
+        additionalInformation: "[redacted/dynamic]",
+      },
+    });
+
+    webhookReceiver.close();
+  });
+});
+
+test.describe("BOOKING_REQUESTED", async () => {
+  test("can book an event that requires confirmation and get a booking requested event", async ({
+    page,
+    users,
+  }) => {
+    const webhookReceiver = createHttpServer();
+    // --- create a user
+    const user = await users.create();
+
+    // --- login as that user
+    await user.login();
+
+    await page.goto(`/settings/developer/webhooks`);
+
+    // --- add webhook
+    await page.click('[data-testid="new_webhook"]');
+
+    await page.fill('[name="subscriberUrl"]', webhookReceiver.url);
+
+    await page.fill('[name="secret"]', "secret");
+
+    await Promise.all([
+      page.click("[type=submit]"),
+      page.waitForURL((url) => url.pathname.endsWith("/settings/developer/webhooks")),
+    ]);
+
+    // page contains the url
+    expect(page.locator(`text='${webhookReceiver.url}'`)).toBeDefined();
+
+    // --- visit user page
+    await page.goto(`/${user.username}`);
+
+    // --- book the user's opt in
+    await bookOptinEvent(page);
+
+    // --- check that webhook was called
+
+    await waitFor(() => {
+      expect(webhookReceiver.requestList.length).toBe(1);
+    });
+    const [request] = webhookReceiver.requestList;
+    const body = request.body as any;
+
+    // remove dynamic properties that differs depending on where you run the tests
+    const dynamic = "[redacted/dynamic]";
+    body.createdAt = dynamic;
+    body.payload.startTime = dynamic;
+    body.payload.endTime = dynamic;
+    body.payload.location = dynamic;
+    for (const attendee of body.payload.attendees) {
+      attendee.timeZone = dynamic;
+      attendee.language = dynamic;
+    }
+    body.payload.organizer.id = dynamic;
+    body.payload.organizer.email = dynamic;
+    body.payload.organizer.timeZone = dynamic;
+    body.payload.organizer.language = dynamic;
+    body.payload.uid = dynamic;
+    body.payload.bookingId = dynamic;
+    body.payload.additionalInformation = dynamic;
+    body.payload.requiresConfirmation = dynamic;
+    body.payload.eventTypeId = dynamic;
+    body.payload.videoCallData = dynamic;
+    body.payload.appsStatus = dynamic;
+    body.payload.metadata.videoCallUrl = dynamic;
+
+    expect(body).toMatchObject({
+      triggerEvent: "BOOKING_REQUESTED",
+      createdAt: "[redacted/dynamic]",
+      payload: {
+        type: "Opt in",
+        title: "Opt in between Nameless and Test Testson",
+        customInputs: {},
+        startTime: "[redacted/dynamic]",
+        endTime: "[redacted/dynamic]",
+        organizer: {
+          id: "[redacted/dynamic]",
+          name: "Nameless",
+          email: "[redacted/dynamic]",
+          timeZone: "[redacted/dynamic]",
+          language: "[redacted/dynamic]",
+        },
+        responses: {
+          email: {
+            value: "test@example.com",
+            label: "email_address",
+          },
+          name: {
+            value: "Test Testson",
+            label: "your_name",
+          },
+        },
+        userFieldsResponses: {},
+        attendees: [
+          {
+            email: "test@example.com",
+            name: "Test Testson",
+            timeZone: "[redacted/dynamic]",
+            language: "[redacted/dynamic]",
+          },
+        ],
+        location: "[redacted/dynamic]",
+        destinationCalendar: null,
+        requiresConfirmation: "[redacted/dynamic]",
+        eventTypeId: "[redacted/dynamic]",
+        uid: "[redacted/dynamic]",
+        eventTitle: "Opt in",
+        eventDescription: null,
+        price: 0,
+        currency: "usd",
+        length: 30,
+        bookingId: "[redacted/dynamic]",
+        status: "PENDING",
+        additionalInformation: "[redacted/dynamic]",
+        metadata: { videoCallUrl: "[redacted/dynamic]" },
+      },
+    });
+
+    webhookReceiver.close();
+  });
 });
diff --git a/apps/web/public/static/locales/en/common.json b/apps/web/public/static/locales/en/common.json
index 4aecb5157e..e920d84b0b 100644
--- a/apps/web/public/static/locales/en/common.json
+++ b/apps/web/public/static/locales/en/common.json
@@ -374,6 +374,8 @@
   "booking_rescheduled": "Booking Rescheduled",
   "recording_ready":"Recording Download Link Ready",
   "booking_created": "Booking Created",
+  "booking_rejected":"Booking Rejected",
+  "booking_requested":"Booking Requested",
   "meeting_ended": "Meeting Ended",
   "form_submitted": "Form Submitted",
   "event_triggers": "Event Triggers",
diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index a1a9fc73d1..caf13c75e3 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -33,6 +33,7 @@ import {
 } from "@calcom/emails";
 import { getBookingFieldsWithSystemFields } from "@calcom/features/bookings/lib/getBookingFields";
 import { getCalEventResponses } from "@calcom/features/bookings/lib/getCalEventResponses";
+import { handleWebhookTrigger } from "@calcom/features/bookings/lib/handleWebhookTrigger";
 import {
   allowDisablingAttendeeConfirmationEmails,
   allowDisablingHostConfirmationEmails,
@@ -40,6 +41,7 @@ import {
 import { deleteScheduledEmailReminder } from "@calcom/features/ee/workflows/lib/reminders/emailReminderManager";
 import { scheduleWorkflowReminders } from "@calcom/features/ee/workflows/lib/reminders/reminderScheduler";
 import { deleteScheduledSMSReminder } from "@calcom/features/ee/workflows/lib/reminders/smsReminderManager";
+import type { GetSubscriberOptions } from "@calcom/features/webhooks/lib/getWebhooks";
 import getWebhooks from "@calcom/features/webhooks/lib/getWebhooks";
 import { isPrismaObjOrUndefined, parseRecurringEvent } from "@calcom/lib";
 import { getVideoCallUrlFromCalEvent } from "@calcom/lib/CalEventParser";
@@ -72,7 +74,6 @@ import type { EventResult, PartialReference } from "@calcom/types/EventManager";
 import type { WorkingHours, TimeRange as DateOverride } from "@calcom/types/schedule";
 
 import type { EventTypeInfo } from "../../webhooks/lib/sendPayload";
-import sendPayload from "../../webhooks/lib/sendPayload";
 import getBookingResponsesSchema from "./getBookingResponsesSchema";
 
 const translator = short();
@@ -2092,16 +2093,44 @@ async function handler(
         videoCallUrl: getVideoCallUrlFromCalEvent(evt),
       }
     : undefined;
+
+  const eventTypeInfo: EventTypeInfo = {
+    eventTitle: eventType.title,
+    eventDescription: eventType.description,
+    requiresConfirmation: requiresConfirmation || null,
+    price: paymentAppData.price,
+    currency: eventType.currency,
+    length: eventType.length,
+  };
+  const webhookData = {
+    ...evt,
+    ...eventTypeInfo,
+    bookingId: booking?.id,
+    rescheduleUid,
+    rescheduleStartTime: originalRescheduledBooking?.startTime
+      ? dayjs(originalRescheduledBooking?.startTime).utc().format()
+      : undefined,
+    rescheduleEndTime: originalRescheduledBooking?.endTime
+      ? dayjs(originalRescheduledBooking?.endTime).utc().format()
+      : undefined,
+    metadata: { ...metadata, ...reqBody.metadata },
+    eventTypeId,
+    status: "ACCEPTED",
+    smsReminderNumber: booking?.smsReminderNumber || undefined,
+  };
+  const subscriberOptions: GetSubscriberOptions = {
+    userId: organizerUser.id,
+    eventTypeId,
+    triggerEvent: WebhookTriggerEvents.BOOKING_CREATED,
+    teamId: eventType.team?.id,
+  };
+
   if (isConfirmedByDefault) {
     const eventTrigger: WebhookTriggerEvents = rescheduleUid
       ? WebhookTriggerEvents.BOOKING_RESCHEDULED
       : WebhookTriggerEvents.BOOKING_CREATED;
-    const subscriberOptions = {
-      userId: organizerUser.id,
-      eventTypeId,
-      triggerEvent: eventTrigger,
-      teamId: eventType.team?.id,
-    };
+
+    subscriberOptions.triggerEvent = eventTrigger;
 
     const subscriberOptionsMeetingEnded = {
       userId: organizerUser.id,
@@ -2125,48 +2154,14 @@ async function handler(
       log.error("Error while running scheduledJobs for booking", error);
     }
 
-    try {
-      // Send Webhook call if hooked to BOOKING_CREATED & BOOKING_RESCHEDULED
-      const subscribers = await getWebhooks(subscriberOptions);
-      console.log("evt:", {
-        ...evt,
-        metadata: reqBody.metadata,
-      });
-      const bookingId = booking?.id;
-
-      const eventTypeInfo: EventTypeInfo = {
-        eventTitle: eventType.title,
-        eventDescription: eventType.description,
-        requiresConfirmation: requiresConfirmation || null,
-        price: paymentAppData.price,
-        currency: eventType.currency,
-        length: eventType.length,
-      };
-
-      const promises = subscribers.map((sub) =>
-        sendPayload(sub.secret, eventTrigger, new Date().toISOString(), sub, {
-          ...evt,
-          ...eventTypeInfo,
-          bookingId,
-          rescheduleUid,
-          rescheduleStartTime: originalRescheduledBooking?.startTime
-            ? dayjs(originalRescheduledBooking?.startTime).utc().format()
-            : undefined,
-          rescheduleEndTime: originalRescheduledBooking?.endTime
-            ? dayjs(originalRescheduledBooking?.endTime).utc().format()
-            : undefined,
-          metadata: { ...metadata, ...reqBody.metadata },
-          eventTypeId,
-          status: "ACCEPTED",
-          smsReminderNumber: booking?.smsReminderNumber || undefined,
-        }).catch((e) => {
-          console.error(`Error executing webhook for event: ${eventTrigger}, URL: ${sub.subscriberUrl}`, e);
-        })
-      );
-      await Promise.all(promises);
-    } catch (error) {
-      log.error("Error while sending webhook", error);
-    }
+    // Send Webhook call if hooked to BOOKING_CREATED & BOOKING_RESCHEDULED
+    await handleWebhookTrigger({ subscriberOptions, eventTrigger, webhookData });
+  } else if (eventType.requiresConfirmation) {
+    // if eventType requires confirmation we will trigger the BOOKING REQUESTED Webhook
+    const eventTrigger: WebhookTriggerEvents = WebhookTriggerEvents.BOOKING_REQUESTED;
+    subscriberOptions.triggerEvent = eventTrigger;
+    webhookData.status = "PENDING";
+    await handleWebhookTrigger({ subscriberOptions, eventTrigger, webhookData });
   }
 
   // Avoid passing referencesToCreate with id unique constrain values
diff --git a/packages/features/bookings/lib/handleWebhookTrigger.ts b/packages/features/bookings/lib/handleWebhookTrigger.ts
new file mode 100644
index 0000000000..7b510c820a
--- /dev/null
+++ b/packages/features/bookings/lib/handleWebhookTrigger.ts
@@ -0,0 +1,29 @@
+import getWebhooks from "@calcom/features/webhooks/lib/getWebhooks";
+import type { GetSubscriberOptions } from "@calcom/features/webhooks/lib/getWebhooks";
+import type { WebhookDataType } from "@calcom/features/webhooks/lib/sendPayload";
+import sendPayload from "@calcom/features/webhooks/lib/sendPayload";
+import logger from "@calcom/lib/logger";
+
+export async function handleWebhookTrigger(args: {
+  subscriberOptions: GetSubscriberOptions;
+  eventTrigger: string;
+  webhookData: Omit<WebhookDataType, "createdAt" | "triggerEvent">;
+}) {
+  try {
+    const subscribers = await getWebhooks(args.subscriberOptions);
+
+    const promises = subscribers.map((sub) =>
+      sendPayload(sub.secret, args.eventTrigger, new Date().toISOString(), sub, args.webhookData).catch(
+        (e) => {
+          console.error(
+            `Error executing webhook for event: ${args.eventTrigger}, URL: ${sub.subscriberUrl}`,
+            e
+          );
+        }
+      )
+    );
+    await Promise.all(promises);
+  } catch (error) {
+    logger.error("Error while sending webhook", error);
+  }
+}
diff --git a/packages/features/webhooks/components/WebhookForm.tsx b/packages/features/webhooks/components/WebhookForm.tsx
index 2e4fc7310c..07071845ed 100644
--- a/packages/features/webhooks/components/WebhookForm.tsx
+++ b/packages/features/webhooks/components/WebhookForm.tsx
@@ -32,6 +32,8 @@ const WEBHOOK_TRIGGER_EVENTS_GROUPED_BY_APP_V2: Record<string, WebhookTriggerEve
   core: [
     { value: WebhookTriggerEvents.BOOKING_CANCELLED, label: "booking_cancelled" },
     { value: WebhookTriggerEvents.BOOKING_CREATED, label: "booking_created" },
+    { value: WebhookTriggerEvents.BOOKING_REJECTED, label: "booking_rejected"},
+    { value: WebhookTriggerEvents.BOOKING_REQUESTED, label: "booking_requested"},
     { value: WebhookTriggerEvents.BOOKING_RESCHEDULED, label: "booking_rescheduled" },
     { value: WebhookTriggerEvents.MEETING_ENDED, label: "meeting_ended" },
     { value: WebhookTriggerEvents.RECORDING_READY, label: "recording_ready" },
diff --git a/packages/features/webhooks/lib/constants.ts b/packages/features/webhooks/lib/constants.ts
index 2922fcd133..c91d7c4388 100644
--- a/packages/features/webhooks/lib/constants.ts
+++ b/packages/features/webhooks/lib/constants.ts
@@ -8,6 +8,8 @@ export const WEBHOOK_TRIGGER_EVENTS_GROUPED_BY_APP = {
     WebhookTriggerEvents.BOOKING_CREATED,
     WebhookTriggerEvents.BOOKING_RESCHEDULED,
     WebhookTriggerEvents.MEETING_ENDED,
+    WebhookTriggerEvents.BOOKING_REQUESTED,
+    WebhookTriggerEvents.BOOKING_REJECTED,
     WebhookTriggerEvents.RECORDING_READY,
   ] as const,
   "routing-forms": [WebhookTriggerEvents.FORM_SUBMITTED] as const,
diff --git a/packages/features/webhooks/lib/sendPayload.ts b/packages/features/webhooks/lib/sendPayload.ts
index 9042cac304..814c8cdd7e 100644
--- a/packages/features/webhooks/lib/sendPayload.ts
+++ b/packages/features/webhooks/lib/sendPayload.ts
@@ -16,7 +16,7 @@ export type EventTypeInfo = {
   length?: number | null;
 };
 
-type WebhookDataType = CalendarEvent &
+export type WebhookDataType = CalendarEvent &
   EventTypeInfo & {
     metadata?: { [key: string]: string };
     bookingId?: number;
diff --git a/packages/prisma/migrations/20230522115850_add_enum_booking_requested_booking_rejected/migration.sql b/packages/prisma/migrations/20230522115850_add_enum_booking_requested_booking_rejected/migration.sql
new file mode 100644
index 0000000000..5a7a0359a8
--- /dev/null
+++ b/packages/prisma/migrations/20230522115850_add_enum_booking_requested_booking_rejected/migration.sql
@@ -0,0 +1,3 @@
+-- AlterEnum
+ALTER TYPE "WebhookTriggerEvents" ADD VALUE 'BOOKING_REQUESTED';
+ALTER TYPE "WebhookTriggerEvents" ADD VALUE 'BOOKING_REJECTED';
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 000263cb42..e5f4e1cf5f 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -495,7 +495,9 @@ enum PaymentOption {
 enum WebhookTriggerEvents {
   BOOKING_CREATED
   BOOKING_RESCHEDULED
+  BOOKING_REQUESTED
   BOOKING_CANCELLED
+  BOOKING_REJECTED
   FORM_SUBMITTED
   MEETING_ENDED
   RECORDING_READY
diff --git a/packages/trpc/server/routers/viewer/bookings/confirm.handler.ts b/packages/trpc/server/routers/viewer/bookings/confirm.handler.ts
index 7b2a3b9941..95fdc49af5 100644
--- a/packages/trpc/server/routers/viewer/bookings/confirm.handler.ts
+++ b/packages/trpc/server/routers/viewer/bookings/confirm.handler.ts
@@ -4,10 +4,12 @@ import appStore from "@calcom/app-store";
 import { sendDeclinedEmails } from "@calcom/emails";
 import { getCalEventResponses } from "@calcom/features/bookings/lib/getCalEventResponses";
 import { handleConfirmation } from "@calcom/features/bookings/lib/handleConfirmation";
+import { handleWebhookTrigger } from "@calcom/features/bookings/lib/handleWebhookTrigger";
+import type { EventTypeInfo } from "@calcom/features/webhooks/lib/sendPayload";
 import { isPrismaObjOrUndefined, parseRecurringEvent } from "@calcom/lib";
 import { getTranslation } from "@calcom/lib/server";
 import { prisma } from "@calcom/prisma";
-import { BookingStatus, MembershipRole, SchedulingType } from "@calcom/prisma/enums";
+import { BookingStatus, MembershipRole, SchedulingType, WebhookTriggerEvents } from "@calcom/prisma/enums";
 import type { CalendarEvent } from "@calcom/types/Calendar";
 import type { IAbstractPaymentService } from "@calcom/types/PaymentService";
 
@@ -304,6 +306,31 @@ export const confirmHandler = async ({ ctx, input }: ConfirmOptions) => {
     }
 
     await sendDeclinedEmails(evt);
+    // send BOOKING_REJECTED webhooks
+    const subscriberOptions = {
+      userId: booking.userId,
+      eventTypeId: booking.eventTypeId,
+      triggerEvent: WebhookTriggerEvents.BOOKING_REJECTED,
+      teamId: booking.eventType?.teamId,
+    };
+    const eventTrigger: WebhookTriggerEvents = WebhookTriggerEvents.BOOKING_REJECTED;
+    const eventTypeInfo: EventTypeInfo = {
+      eventTitle: booking.eventType?.title,
+      eventDescription: booking.eventType?.description,
+      requiresConfirmation: booking.eventType?.requiresConfirmation || null,
+      price: booking.eventType?.price,
+      currency: booking.eventType?.currency,
+      length: booking.eventType?.length,
+    };
+    const webhookData = {
+      ...evt,
+      ...eventTypeInfo,
+      bookingId,
+      eventTypeId: booking.eventType?.id,
+      status: BookingStatus.REJECTED,
+      smsReminderNumber: booking.smsReminderNumber || undefined,
+    };
+    await handleWebhookTrigger({ subscriberOptions, eventTrigger, webhookData });
   }
 
   const message = "Booking " + confirmed ? "confirmed" : "rejected";