diff --git a/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts b/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts
new file mode 100644
index 0000000000..f2de0d362b
--- /dev/null
+++ b/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts
@@ -0,0 +1,445 @@
+import { loginUser } from "../fixtures/regularBookings";
+import { test } from "../lib/fixtures";
+
+test.describe("Booking With Checkbox Group 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 Checkbox Group Question and Address Question", () => {
+    test("Checkbox Group required and Address required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+        fillText: "Test Checkbox Group 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("Checkbox Group and Address not required", async ({ bookingPage }) => {
+      await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+        fillText: "Test Checkbox Group question and Address question (only checkbox 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 Checkbox Group Question and Phone Question", () => {
+      test("Checkbox Group required and Phone required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Phone not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Phone question (only checkbox 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 Checkbox Group Question and checkbox Question", () => {
+      test("Checkbox Group required and checkbox required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and checkbox not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and checkbox (only checkbox 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 Checkbox Group Question and Long text Question", () => {
+      test("Checkbox Group required and Long text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Long text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Long Text question (only checkbox 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 Checkbox Group Question and Multi email Question", () => {
+      test("Checkbox Group required and Multi email required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Multi email not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Multi Email question (only checkbox 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 Checkbox Group Question and multiselect Question", () => {
+      test("Checkbox Group required and multiselect text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and multiselect text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Multi Select question (only checkbox 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 Checkbox Group Question and Number Question", () => {
+      test("Checkbox Group required and Number required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Number not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Number question (only checkbox 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 Checkbox Group Question and Radio group Question", () => {
+      test("Checkbox Group required and Radio group required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox test", true);
+        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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Radio group not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox test", true);
+        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: "checkbox",
+          fillText: "Test Checkbox Group question and Radio question (only checkbox 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 Checkbox Group Question and select Question", () => {
+      test("Checkbox Group required and select required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and select not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Select question (only checkbox 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 Checkbox Group Question and Short text question", () => {
+      test("Checkbox Group required and Short Text required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group 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("Checkbox Group and Short Text not required", async ({ bookingPage }) => {
+        await bookingPage.addQuestion("checkbox", "checkbox-test", "checkbox 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: "checkbox",
+          fillText: "Test Checkbox Group question and Text question (only checkbox 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 4b5585165c..9a5d6e881b 100644
--- a/apps/web/playwright/fixtures/regularBookings.ts
+++ b/apps/web/playwright/fixtures/regularBookings.ts
@@ -207,6 +207,14 @@ export function createBookingPageFixture(page: Page) {
       await eventTypePage.getByPlaceholder(reschedulePlaceholderText).click();
       await eventTypePage.getByPlaceholder(reschedulePlaceholderText).fill("Test reschedule");
       await eventTypePage.getByTestId("confirm-reschedule-button").click();
+      await eventTypePage.waitForTimeout(400);
+      if (
+        await eventTypePage.getByRole("heading", { name: "Could not reschedule the meeting." }).isVisible()
+      ) {
+        await eventTypePage.getByTestId("back").click();
+        await eventTypePage.getByTestId("time").last().click();
+        await eventTypePage.getByTestId("confirm-reschedule-button").click();
+      }
     },
 
     assertBookingRescheduled: async (page: Page) => {
@@ -261,6 +269,14 @@ export function createBookingPageFixture(page: Page) {
       options.isRequired && (await fillQuestion(eventTypePage, secondQuestion, customLocators));
 
       await eventTypePage.getByTestId(confirmButton).click();
+      await eventTypePage.waitForTimeout(400);
+      if (await eventTypePage.getByRole("heading", { name: "Could not book the meeting." }).isVisible()) {
+        await eventTypePage.getByTestId("back").click();
+        await eventTypePage.getByTestId("time").last().click();
+        await fillQuestion(eventTypePage, question, customLocators);
+        options.isRequired && (await fillQuestion(eventTypePage, secondQuestion, customLocators));
+        await eventTypePage.getByTestId(confirmButton).click();
+      }
       const scheduleSuccessfullyPage = eventTypePage.getByText(scheduleSuccessfullyText);
       await scheduleSuccessfullyPage.waitFor({ state: "visible" });
       await expect(scheduleSuccessfullyPage).toBeVisible();