diff --git a/apps/web/playwright/booking/multipleEmailQuestion.e2e.ts b/apps/web/playwright/booking/multipleEmailQuestion.e2e.ts
new file mode 100644
index 0000000000..77a4b754d6
--- /dev/null
+++ b/apps/web/playwright/booking/multipleEmailQuestion.e2e.ts
@@ -0,0 +1,553 @@
+import { loginUser } from "../fixtures/regularBookings";
+import { test } from "../lib/fixtures";
+
+test.describe("Booking With Multiple Email Question and Each Other Question", () => {
+  const bookingOptions = { hasPlaceholder: true, isRequired: true };
+
+  test.beforeEach(async ({ page, users, bookingPage }) => {
+    await loginUser(users);
+    await page.goto("/event-types");
+    await bookingPage.goToEventType("30 min");
+    await bookingPage.goToTab("event_advanced_tab_title");
+  });
+
+  test.describe("Booking With Multiple Email Question and Address Question", () => {
+    test("Multiple Email required and Address required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("address", "address-test", "address test", true, "address test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Address question (both required)",
+        secondQuestion: "address",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and Address not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("address", "address-test", "address test", false, "address test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Address question (only Multiple Email required)",
+        secondQuestion: "address",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and checkbox group Question", () => {
+    test("Multiple Email required and checkbox group required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox test", true);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and checkbox group question (both required)",
+        secondQuestion: "checkbox",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and checkbox group not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox test", false);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and checkbox group question (only Multiple Email required)",
+        secondQuestion: "checkbox",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and checkbox Question", () => {
+    test("Multiple Email required and checkbox required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("boolean", "boolean-test", "boolean test", true);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and checkbox question (both required)",
+        secondQuestion: "boolean",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and checkbox not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("boolean", "boolean-test", "boolean test", false);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and checkbox (only Multiple Email required)",
+        secondQuestion: "boolean",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and Long text Question", () => {
+    test("Multiple Email required and Long text required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("textarea", "textarea-test", "textarea test", true, "textarea test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Long Text question (both required)",
+        secondQuestion: "textarea",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and Long text not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("textarea", "textarea-test", "textarea test", false, "textarea test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Long Text question (only Multiple Email required)",
+        secondQuestion: "textarea",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and multiselect Question", () => {
+    test("Multiple Email required and multiselect text required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("multiselect", "multiselect-test", "multiselect test", true);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Multi Select question (both required)",
+        secondQuestion: "multiselect",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and multiselect text not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("multiselect", "multiselect-test", "multiselect test", false);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Multi Select question (only  Multiple Email required)",
+        secondQuestion: "multiselect",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and Number Question", () => {
+    test("Multiple Email required and Number required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("number", "number-test", "number test", true, "number test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Number question (both required)",
+        secondQuestion: "number",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and Number not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("number", "number-test", "number test", false, "number test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Number question (only Multiple Email required)",
+        secondQuestion: "number",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple email Question and phone Question", () => {
+    test("Multiple email required and Phone required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("phone", "phone-test", "phone test", true, "phone test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Phone question (both required)",
+        secondQuestion: "phone",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple email and Phone not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("phone", "phone-test", "phone test", false, "phone test");
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Phone question (both required)",
+        secondQuestion: "phone",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+  });
+
+  test.describe("Booking With Multiple Email Question and Radio group Question", () => {
+    test("Multiple Email required and Radio group required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test  Multiple Email question and Radio question (both required)",
+        secondQuestion: "radio",
+        options: bookingOptions,
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test("Multiple Email and Radio group not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion(
+        "multiemail",
+        "multiemail-test",
+        "multiemail test",
+        true,
+        "multiemail test"
+      );
+      await bookingPage.addQuestion("radio", "radio-test", "radio test", false);
+      await bookingPage.updateEventType();
+      const eventTypePage = await bookingPage.previewEventType();
+      await bookingPage.selectTimeSlot(eventTypePage);
+      await bookingPage.fillAndConfirmBooking({
+        eventTypePage,
+        placeholderText: "Please share anything that will help prepare for our meeting.",
+        question: "multiemail",
+        fillText: "Test Multiple Email question and Radio question (only  Multiple Email required)",
+        secondQuestion: "radio",
+        options: { ...bookingOptions, isRequired: false },
+      });
+      await bookingPage.rescheduleBooking(eventTypePage);
+      await bookingPage.assertBookingRescheduled(eventTypePage);
+      await bookingPage.cancelBooking(eventTypePage);
+      await bookingPage.assertBookingCanceled(eventTypePage);
+    });
+
+    test.describe("Booking With Multiple Email Question and select Question", () => {
+      test("Multiple Email required and select required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          true,
+          "multiemail test"
+        );
+        await bookingPage.addQuestion("select", "select-test", "select test", true, "select test");
+        await bookingPage.updateEventType();
+        const eventTypePage = await bookingPage.previewEventType();
+        await bookingPage.selectTimeSlot(eventTypePage);
+        await bookingPage.fillAndConfirmBooking({
+          eventTypePage,
+          placeholderText: "Please share anything that will help prepare for our meeting.",
+          question: "multiemail",
+          fillText: "Test Multiple Email question and Select question (both required)",
+          secondQuestion: "select",
+          options: bookingOptions,
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+
+      test("Multiple Email and select not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          true,
+          "multiemail test"
+        );
+        await bookingPage.addQuestion("select", "select-test", "select test", false, "select test");
+        await bookingPage.updateEventType();
+        const eventTypePage = await bookingPage.previewEventType();
+        await bookingPage.selectTimeSlot(eventTypePage);
+        await bookingPage.fillAndConfirmBooking({
+          eventTypePage,
+          placeholderText: "Please share anything that will help prepare for our meeting.",
+          question: "multiemail",
+          fillText: "Test Multiple Email question and Select question (only Multiple Email required)",
+          secondQuestion: "select",
+          options: { ...bookingOptions, isRequired: false },
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+    });
+
+    test.describe("Booking With Multiple Email Question and Short text question", () => {
+      test("Multiple Email required and Short text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          true,
+          "multiemail test"
+        );
+        await bookingPage.addQuestion("text", "text-test", "text test", true, "text test");
+        await bookingPage.updateEventType();
+        const eventTypePage = await bookingPage.previewEventType();
+        await bookingPage.selectTimeSlot(eventTypePage);
+        await bookingPage.fillAndConfirmBooking({
+          eventTypePage,
+          placeholderText: "Please share anything that will help prepare for our meeting.",
+          question: "multiemail",
+          fillText: "Test Multiple Email question and Text question (both required)",
+          secondQuestion: "text",
+          options: bookingOptions,
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+
+      test("Multiple Email and Short text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          true,
+          "multiemail test"
+        );
+        await bookingPage.addQuestion("text", "text-test", "text test", false, "text test");
+        await bookingPage.updateEventType();
+        const eventTypePage = await bookingPage.previewEventType();
+        await bookingPage.selectTimeSlot(eventTypePage);
+        await bookingPage.fillAndConfirmBooking({
+          eventTypePage,
+          placeholderText: "Please share anything that will help prepare for our meeting.",
+          question: "multiemail",
+          fillText: "Test Multiple Email question and Text question (only Multiple Email required)",
+          secondQuestion: "text",
+          options: { ...bookingOptions, isRequired: false },
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+    });
+  });
+});
diff --git a/apps/web/playwright/booking/phoneQuestion.e2e.ts b/apps/web/playwright/booking/phoneQuestion.e2e.ts
index 481b489cbc..05b8d1cc08 100644
--- a/apps/web/playwright/booking/phoneQuestion.e2e.ts
+++ b/apps/web/playwright/booking/phoneQuestion.e2e.ts
@@ -402,7 +402,6 @@ test.describe("Booking With Phone Question and Each Other Question", () => {
     });
 
     test.describe("Booking With Phone Question and Short text question", () => {
-      const bookingOptions = { hasPlaceholder: true, isRequired: true };
       test("Phone and Short text required", async ({ bookingPage }) => {
         await bookingPage.addQuestion("phone", "phone-test", "phone test", true, "phone test");
         await bookingPage.addQuestion("text", "text-test", "text test", true, "text test");