diff --git a/apps/web/playwright/booking/radioGroupQuestion.e2e.ts b/apps/web/playwright/booking/radioGroupQuestion.e2e.ts
new file mode 100644
index 0000000000..6f6ef77e1a
--- /dev/null
+++ b/apps/web/playwright/booking/radioGroupQuestion.e2e.ts
@@ -0,0 +1,444 @@
+import { loginUser } from "../fixtures/regularBookings";
+import { test } from "../lib/fixtures";
+
+test.describe("Booking With Radio 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 Radio Question and Address Question", () => {
+    test("Radio required and Address required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+      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: "radio",
+        fillText: "Test Radio 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("Radio and Address not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+      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: "radio",
+        fillText: "Test Radio question and Address question (only radio 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 Radio Question and checkbox group Question", () => {
+      test("Radio required and checkbox group required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and checkbox group not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and checkbox group question (only radio 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 Radio Question and checkbox Question", () => {
+      test("Radio required and checkbox required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and checkbox not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and checkbox (only radio 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 Radio Question and Long text Question", () => {
+      test("Radio required and Long text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and Long text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Long Text question (only radio 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 Radio Question and Multi email Question", () => {
+      test("Radio required and Multi email required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          true,
+          "multiemail 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: "radio",
+          fillText: "Test Radio question and Multi Email question (both required)",
+          secondQuestion: "multiemail",
+          options: bookingOptions,
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+
+      test("Radio and Multi email not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        await bookingPage.addQuestion(
+          "multiemail",
+          "multiemail-test",
+          "multiemail test",
+          false,
+          "multiemail 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: "radio",
+          fillText: "Test Radio question and Multi Email question (only radio required)",
+          secondQuestion: "multiemail",
+          options: { ...bookingOptions, isRequired: false },
+        });
+        await bookingPage.rescheduleBooking(eventTypePage);
+        await bookingPage.assertBookingRescheduled(eventTypePage);
+        await bookingPage.cancelBooking(eventTypePage);
+        await bookingPage.assertBookingCanceled(eventTypePage);
+      });
+    });
+
+    test.describe("Booking With Radio Question and multiselect Question", () => {
+      test("Radio required and multiselect text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and multiselect text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Multi Select question (only radio 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 Radio Question and Number Question", () => {
+      test("Radio required and Number required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and Number not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Number question (only radio 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 Radio Question and Phone Question", () => {
+      test("Radio required and Phone required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and Phone not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Phone question (only radio 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 Radio Question and select Question", () => {
+      test("Radio required and select required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and select not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Select question (only radio 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 Radio Question and Short text question", () => {
+      test("Radio required and Short text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio 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("Radio and Short text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("radio", "radio-test", "radio test", true);
+        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: "radio",
+          fillText: "Test Radio question and Text question (only radio 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/fixtures/regularBookings.ts b/apps/web/playwright/fixtures/regularBookings.ts
index 9a5d6e881b..5fea0d62fa 100644
--- a/apps/web/playwright/fixtures/regularBookings.ts
+++ b/apps/web/playwright/fixtures/regularBookings.ts
@@ -182,6 +182,7 @@ export function createBookingPageFixture(page: Page) {
     selectFirstAvailableTime: async () => {
       await page.getByTestId("time").first().click();
     },
+
     fillRescheduleReasonAndConfirm: async () => {
       await page.getByPlaceholder(reschedulePlaceholderText).click();
       await page.getByPlaceholder(reschedulePlaceholderText).fill("Test reschedule");