diff --git a/apps/web/playwright/booking/allQuestionse2e/bookingWithAllQuestions.e2e.ts b/apps/web/playwright/booking/allQuestionse2e/bookingWithAllQuestions.e2e.ts
new file mode 100644
index 0000000000..f32c77efe2
--- /dev/null
+++ b/apps/web/playwright/booking/allQuestionse2e/bookingWithAllQuestions.e2e.ts
@@ -0,0 +1,43 @@
+import { test } from "../../lib/fixtures";
+import { scheduleAllQuestionsBooking } from "../utils/scheduleAllBookings";
+
+test.describe.configure({ mode: "parallel" });
+
+test.afterEach(({ users }) => users.deleteAll());
+
+test.describe("Booking With All Questions", () => {
+  const bookingOptions = { isAllRequired: true };
+
+  test("Selecting and filling all questions as required", async ({ page, users }) => {
+    const allQuestions = [
+      "phone",
+      "address",
+      "checkbox",
+      "boolean",
+      "textarea",
+      "multiemail",
+      "multiselect",
+      "number",
+      "radio",
+      "select",
+      "text",
+    ];
+    await scheduleAllQuestionsBooking(page, allQuestions, users, bookingOptions);
+  });
+  test("Selecting and filling all questions as optional", async ({ page, users }) => {
+    const allQuestions = [
+      "phone",
+      "address",
+      "checkbox",
+      "boolean",
+      "textarea",
+      "multiemail",
+      "multiselect",
+      "number",
+      "radio",
+      "select",
+      "text",
+    ];
+    await scheduleAllQuestionsBooking(page, allQuestions, users, { ...bookingOptions, isAllRequired: false });
+  });
+});
diff --git a/apps/web/playwright/booking/utils/bookingUtils.ts b/apps/web/playwright/booking/utils/bookingUtils.ts
new file mode 100644
index 0000000000..d6324f64cb
--- /dev/null
+++ b/apps/web/playwright/booking/utils/bookingUtils.ts
@@ -0,0 +1,244 @@
+import { expect, type Page } from "@playwright/test";
+
+import type { Fixtures } from "@calcom/web/playwright/lib/fixtures";
+
+const EMAIL = "test@test.com";
+const EMAIL2 = "test2@test.com";
+const PHONE = "+55 (32) 983289947";
+const scheduleSuccessfullyText = "This meeting is scheduled";
+const reschedulePlaceholderText = "Let others know why you need to reschedule";
+
+interface QuestionActions {
+  [key: string]: () => Promise<void>;
+}
+
+type BookingOptions = {
+  hasPlaceholder?: boolean;
+  isReschedule?: boolean;
+  isRequired?: boolean;
+};
+
+type customLocators = {
+  shouldChangeSelectLocator: boolean;
+  shouldUseLastRadioGroupLocator: boolean;
+  shouldUseFirstRadioGroupLocator: boolean;
+  shouldChangeMultiSelectLocator: boolean;
+};
+
+export const loginUser = async (page: Page, users: Fixtures["users"]) => {
+  const pro = await users.create({ name: "testuser" });
+  await pro.apiLogin();
+  await page.goto("/event-types");
+};
+
+const fillQuestion = async (eventTypePage: Page, questionType: string, customLocators: customLocators) => {
+  const questionActions: QuestionActions = {
+    phone: async () => {
+      await eventTypePage.locator('input[name="phone-test"]').clear();
+      await eventTypePage.locator('input[name="phone-test"]').fill(PHONE);
+    },
+    multiemail: async () => {
+      await eventTypePage.getByRole("button", { name: `${questionType} test` }).click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).fill(EMAIL);
+      await eventTypePage.getByTestId("add-another-guest").last().click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).last().fill(EMAIL2);
+    },
+    checkbox: async () => {
+      if (customLocators.shouldUseLastRadioGroupLocator || customLocators.shouldChangeMultiSelectLocator) {
+        await eventTypePage.getByLabel("Option 1").last().click();
+        await eventTypePage.getByLabel("Option 2").last().click();
+      } else if (customLocators.shouldUseFirstRadioGroupLocator) {
+        await eventTypePage.getByLabel("Option 1").first().click();
+        await eventTypePage.getByLabel("Option 2").first().click();
+      } else {
+        await eventTypePage.getByLabel("Option 1").click();
+        await eventTypePage.getByLabel("Option 2").click();
+      }
+    },
+    multiselect: async () => {
+      if (customLocators.shouldChangeMultiSelectLocator) {
+        await eventTypePage.locator("form svg").nth(1).click();
+        await eventTypePage.getByTestId("select-option-Option 1").click();
+      } else {
+        await eventTypePage.locator("form svg").last().click();
+        await eventTypePage.getByTestId("select-option-Option 1").click();
+      }
+    },
+    boolean: async () => {
+      await eventTypePage.getByLabel(`${questionType} test`).check();
+    },
+    radio: async () => {
+      await eventTypePage.locator('[id="radio-test\\.option\\.0\\.radio"]').click();
+    },
+    select: async () => {
+      if (customLocators.shouldChangeSelectLocator) {
+        await eventTypePage.locator("form svg").nth(1).click();
+        await eventTypePage.getByTestId("select-option-Option 1").click();
+      } else {
+        await eventTypePage.locator("form svg").last().click();
+        await eventTypePage.getByTestId("select-option-Option 1").click();
+      }
+    },
+    number: async () => {
+      await eventTypePage.getByPlaceholder(`${questionType} test`).click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).fill("123");
+    },
+    address: async () => {
+      await eventTypePage.getByPlaceholder(`${questionType} test`).click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).fill("address test");
+    },
+    textarea: async () => {
+      await eventTypePage.getByPlaceholder(`${questionType} test`).click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).fill("textarea test");
+    },
+    text: async () => {
+      await eventTypePage.getByPlaceholder(`${questionType} test`).click();
+      await eventTypePage.getByPlaceholder(`${questionType} test`).fill("text test");
+    },
+  };
+
+  if (questionActions[questionType]) {
+    await questionActions[questionType]();
+  }
+};
+
+export const fillAndConfirmBooking = async (
+  eventTypePage: Page,
+  placeholderText: string,
+  question: string,
+  fillText: string,
+  secondQuestion: string,
+  options: BookingOptions
+) => {
+  const confirmButton = options.isReschedule ? "confirm-reschedule-button" : "confirm-book-button";
+
+  await expect(eventTypePage.getByText(`${secondQuestion} test`).first()).toBeVisible();
+  await eventTypePage.getByPlaceholder(placeholderText).fill(fillText);
+
+  // Change the selector for specifics cases related to select question
+  const shouldChangeSelectLocator = (question: string, secondQuestion: string): boolean =>
+    question === "select" && ["multiemail", "multiselect"].includes(secondQuestion);
+
+  const shouldUseLastRadioGroupLocator = (question: string, secondQuestion: string): boolean =>
+    question === "radio" && secondQuestion === "checkbox";
+
+  const shouldUseFirstRadioGroupLocator = (question: string, secondQuestion: string): boolean =>
+    question === "checkbox" && secondQuestion === "radio";
+
+  const shouldChangeMultiSelectLocator = (question: string, secondQuestion: string): boolean =>
+    question === "multiselect" && ["address", "checkbox", "multiemail", "select"].includes(secondQuestion);
+
+  const customLocators = {
+    shouldChangeSelectLocator: shouldChangeSelectLocator(question, secondQuestion),
+    shouldUseLastRadioGroupLocator: shouldUseLastRadioGroupLocator(question, secondQuestion),
+    shouldUseFirstRadioGroupLocator: shouldUseFirstRadioGroupLocator(question, secondQuestion),
+    shouldChangeMultiSelectLocator: shouldChangeMultiSelectLocator(question, secondQuestion),
+  };
+
+  // Fill the first question
+  await fillQuestion(eventTypePage, question, customLocators);
+
+  // Fill the second question if is required
+  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();
+};
+
+export const initialCommonSteps = async (
+  bookingPage: Page,
+  question: string,
+  users: Fixtures["users"],
+  secondQuestion: string,
+  message: string,
+  options: BookingOptions
+) => {
+  const firstQuestionHasPlaceholder = [
+    "address",
+    "textarea",
+    "multiemail",
+    "number",
+    "text",
+    "phone",
+  ].includes(question);
+
+  //Logs in a test user and navigates to the event types page.
+  loginUser(bookingPage, users);
+
+  // Go to event type settings
+  await bookingPage.getByRole("link", { name: "30 min" }).click();
+
+  // Go to advanced tab
+  await bookingPage.getByTestId("vertical-tab-event_advanced_tab_title").click();
+
+  // Add first and second question and fill both
+  await bookingPage.getByTestId("add-field").click();
+  await bookingPage.locator("#test-field-type > .bg-default > div > div:nth-child(2)").first().click();
+  await bookingPage.getByTestId(`select-option-${question}`).click();
+  await bookingPage.getByLabel("Identifier").dblclick();
+  await bookingPage.getByLabel("Identifier").fill(`${question}-test`);
+  await bookingPage.getByLabel("Label").click();
+  await bookingPage.getByLabel("Label").fill(`${question} test`);
+
+  // Fill the placeholder if the question has one
+  if (firstQuestionHasPlaceholder) {
+    await bookingPage.getByLabel("Placeholder").click();
+    await bookingPage.getByLabel("Placeholder").fill(`${question} test`);
+  }
+  await bookingPage.getByTestId("field-add-save").click();
+  await bookingPage.getByTestId("add-field").click();
+  await bookingPage.locator("#test-field-type > .bg-default > div > div:nth-child(2)").first().click();
+  await bookingPage.getByTestId(`select-option-${secondQuestion}`).click();
+  await bookingPage.getByLabel("Identifier").dblclick();
+  await bookingPage.getByLabel("Identifier").fill(`${secondQuestion}-test`);
+  await bookingPage.getByLabel("Label").click();
+  await bookingPage.getByLabel("Label").fill(`${secondQuestion} test`);
+  if (options.hasPlaceholder) {
+    await bookingPage.getByLabel("Placeholder").dblclick();
+    await bookingPage.getByLabel("Placeholder").fill(`${secondQuestion} test`);
+  }
+  if (!options.isRequired) {
+    await bookingPage.getByRole("radio", { name: "No" }).click();
+  }
+  await bookingPage.getByTestId("field-add-save").click();
+  await expect(bookingPage.getByTestId(`field-${question}-test`)).toBeVisible();
+  await expect(bookingPage.getByTestId(`field-${secondQuestion}-test`)).toBeVisible();
+  await bookingPage.getByTestId("update-eventtype").click();
+
+  // Go to booking page
+  const eventtypePromise = bookingPage.waitForEvent("popup");
+  await bookingPage.getByTestId("preview-button").click();
+  const eventTypePage = await eventtypePromise;
+
+  // Select the first available time
+  await eventTypePage.getByTestId("time").first().click();
+  fillAndConfirmBooking(
+    eventTypePage,
+    "Please share anything that will help prepare for our meeting.",
+    question,
+    message,
+    secondQuestion,
+    options
+  );
+
+  // Go to final steps
+  await rescheduleAndCancel(eventTypePage);
+};
+export const rescheduleAndCancel = async (eventTypePage: Page) => {
+  await eventTypePage.getByText("Reschedule").click();
+  await eventTypePage.getByTestId("time").first().click();
+  await eventTypePage.getByPlaceholder(reschedulePlaceholderText).click();
+  await eventTypePage.getByPlaceholder(reschedulePlaceholderText).fill("Test reschedule");
+  await eventTypePage.getByTestId("confirm-reschedule-button").click();
+
+  // Check if the rescheduled page is visible
+  await expect(eventTypePage.getByText(scheduleSuccessfullyText)).toBeVisible();
+  await eventTypePage.getByTestId("cancel").click();
+  await eventTypePage.getByTestId("cancel_reason").fill("Test cancel");
+  await eventTypePage.getByTestId("confirm_cancel").click();
+
+  // Check if the cancelled page is visible
+  await expect(eventTypePage.getByTestId("cancelled-headline")).toBeVisible();
+};
diff --git a/apps/web/playwright/booking/utils/scheduleAllBookings.ts b/apps/web/playwright/booking/utils/scheduleAllBookings.ts
new file mode 100644
index 0000000000..de9ee84c44
--- /dev/null
+++ b/apps/web/playwright/booking/utils/scheduleAllBookings.ts
@@ -0,0 +1,145 @@
+import { expect, type Page } from "@playwright/test";
+
+import type { Fixtures } from "@calcom/web/playwright/lib/fixtures";
+
+import { loginUser, rescheduleAndCancel } from "./bookingUtils";
+
+const EMAIL = "test@test.com";
+const PHONE = "+55 (32) 9832847";
+const scheduleSuccessfullyText = "This meeting is scheduled";
+
+type BookingOptions = {
+  isReschedule?: boolean;
+  isAllRequired?: boolean;
+};
+
+// Fill a form field based on the question type
+const fillFormField = async (eventTypePage: Page, question: string) => {
+  switch (question) {
+    case "email":
+      await eventTypePage.getByPlaceholder("Email").click();
+      await eventTypePage.getByPlaceholder("Email").fill(EMAIL);
+      break;
+    case "phone":
+      await eventTypePage.getByPlaceholder("Phone test").click();
+      await eventTypePage.getByPlaceholder("Phone test").fill(PHONE);
+      break;
+    case "address":
+      await eventTypePage.getByPlaceholder("Address test").click();
+      await eventTypePage.getByPlaceholder("Address test").fill("123 Main St, City, Country");
+      break;
+    case "textarea":
+      await eventTypePage.getByPlaceholder("Textarea test").click();
+      await eventTypePage.getByPlaceholder("Textarea test").fill("This is a sample text for textarea.");
+      break;
+    case "select":
+      await eventTypePage.locator("form svg").last().click();
+      await eventTypePage.getByTestId("select-option-Option 1").click();
+      break;
+    case "multiselect":
+      await eventTypePage.locator("form svg").nth(4).click();
+      await eventTypePage.getByTestId("select-option-Option 1").click();
+      break;
+    case "number":
+      await eventTypePage.getByLabel("number test").click();
+      await eventTypePage.getByLabel("number test").fill("123");
+      break;
+    case "radio":
+      await eventTypePage.getByRole("radiogroup").getByText("Option 1").check();
+      break;
+    case "text":
+      await eventTypePage.getByPlaceholder("Text test").click();
+      await eventTypePage.getByPlaceholder("Text test").fill("Sample text");
+      break;
+    case "checkbox":
+      await eventTypePage.getByLabel("Option 1").first().check();
+      await eventTypePage.getByLabel("Option 2").first().check();
+      break;
+    case "boolean":
+      await eventTypePage.getByLabel(`${question} test`).check();
+      break;
+    case "multiemail":
+      await eventTypePage.getByRole("button", { name: "multiemail test" }).click();
+      await eventTypePage.getByPlaceholder("multiemail test").fill(EMAIL);
+      break;
+  }
+};
+
+// Fill all required questions in the booking page
+export const fillAllQuestionsBooking = async (
+  eventTypePage: Page,
+  questions: string[],
+  options: BookingOptions
+) => {
+  const confirmButton = options.isReschedule ? "confirm-reschedule-button" : "confirm-book-button";
+
+  if (options.isAllRequired) {
+    for (const question of questions) {
+      await fillFormField(eventTypePage, question);
+    }
+  }
+
+  await eventTypePage.getByTestId(confirmButton).click();
+  const scheduleSuccessfullyPage = eventTypePage.getByText(scheduleSuccessfullyText);
+  await scheduleSuccessfullyPage.waitFor({ state: "visible" });
+  await expect(scheduleSuccessfullyPage).toBeVisible();
+};
+
+export const scheduleAllQuestionsBooking = async (
+  bookingPage: Page,
+  questions: string[],
+  users: Fixtures["users"],
+  options: BookingOptions
+) => {
+  // Logs in a test user and navigates to the event types page.
+  await loginUser(bookingPage, users);
+
+  // Go to event type settings
+  await bookingPage.getByRole("link", { name: "30 min" }).click();
+
+  // Go to advanced tab
+  await bookingPage.getByTestId("vertical-tab-event_advanced_tab_title").click();
+
+  // Add multiple fields based on the questions array
+  for (const question of questions) {
+    // Check if all questions have isRequired set to true
+    if (options.isAllRequired) {
+      await bookingPage.getByTestId("add-field").click();
+      await bookingPage.locator("#test-field-type > .bg-default > div > div:nth-child(2)").first().click();
+      await bookingPage.getByTestId(`select-option-${question}`).click();
+      await bookingPage.getByLabel("Identifier").dblclick();
+      await bookingPage.getByLabel("Identifier").fill(`${question}-test`);
+      await bookingPage.getByLabel("Label").click();
+      await bookingPage.getByLabel("Label").fill(`${question} test`);
+      if (
+        question !== "number" &&
+        question !== "multiemails" &&
+        question !== "select" &&
+        question !== "checkbox" &&
+        question !== "boolean" &&
+        question !== "multiselect" &&
+        question !== "radio"
+      ) {
+        await bookingPage.getByLabel("Placeholder").dblclick();
+        await bookingPage.getByLabel("Placeholder").fill(`${question} test`);
+      }
+      await bookingPage.getByTestId("field-add-save").click();
+      await expect(bookingPage.getByTestId(`field-${question}-test`)).toBeVisible();
+    }
+  }
+
+  await bookingPage.getByTestId("update-eventtype").click();
+
+  // Go to booking page
+  const eventtypePromise = bookingPage.waitForEvent("popup");
+  await bookingPage.getByTestId("preview-button").click();
+  const eventTypePage = await eventtypePromise;
+
+  // Select the first available time
+  await eventTypePage.getByTestId("time").first().click();
+
+  fillAllQuestionsBooking(eventTypePage, questions, options);
+
+  // Go to final steps
+  await rescheduleAndCancel(eventTypePage);
+};