diff --git a/apps/web/playwright/booking/allQuestions.e2e.ts b/apps/web/playwright/booking/allQuestions.e2e.ts
new file mode 100644
index 0000000000..14870f9672
--- /dev/null
+++ b/apps/web/playwright/booking/allQuestions.e2e.ts
@@ -0,0 +1,110 @@
+/* eslint-disable playwright/no-conditional-in-test */
+import { loginUser } from "../fixtures/regularBookings";
+import { test } from "../lib/fixtures";
+
+test.describe("Booking With All Questions", () => {
+  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");
+  });
+
+  const bookingOptions = { isAllRequired: true };
+
+  test("Selecting and filling all questions as required", async ({ bookingPage }) => {
+    const allQuestions = [
+      "phone",
+      "address",
+      "checkbox",
+      "boolean",
+      "textarea",
+      "multiemail",
+      "multiselect",
+      "number",
+      "radio",
+      "select",
+      "text",
+    ];
+    for (const question of allQuestions) {
+      if (
+        question !== "number" &&
+        question !== "select" &&
+        question !== "checkbox" &&
+        question !== "boolean" &&
+        question !== "multiselect" &&
+        question !== "radio"
+      ) {
+        await bookingPage.addQuestion(
+          question,
+          `${question}-test`,
+          `${question} test`,
+          true,
+          `${question} test`
+        );
+      } else {
+        await bookingPage.addQuestion(question, `${question}-test`, `${question} test`, true);
+      }
+      await bookingPage.checkField(question);
+    }
+
+    await bookingPage.updateEventType();
+    const eventTypePage = await bookingPage.previewEventType();
+    await bookingPage.selectTimeSlot(eventTypePage);
+    await bookingPage.fillAllQuestions(eventTypePage, allQuestions, bookingOptions);
+    await bookingPage.rescheduleBooking(eventTypePage);
+    await bookingPage.assertBookingRescheduled(eventTypePage);
+    await bookingPage.cancelBooking(eventTypePage);
+    await bookingPage.assertBookingCanceled(eventTypePage);
+  });
+
+  test("Selecting and filling all questions as optional", async ({ bookingPage }) => {
+    const allQuestions = [
+      "phone",
+      "address",
+      "checkbox",
+      "boolean",
+      "textarea",
+      "multiemail",
+      "multiselect",
+      "number",
+      "radio",
+      "select",
+      "text",
+    ];
+    for (const question of allQuestions) {
+      if (
+        question !== "number" &&
+        question !== "select" &&
+        question !== "checkbox" &&
+        question !== "boolean" &&
+        question !== "multiselect" &&
+        question !== "radio"
+      ) {
+        await bookingPage.addQuestion(
+          question,
+          `${question}-test`,
+          `${question} test`,
+          false,
+          `${question} test`
+        );
+      } else {
+        await bookingPage.addQuestion(question, `${question}-test`, `${question} test`, false);
+      }
+      await bookingPage.checkField(question);
+    }
+
+    await bookingPage.updateEventType();
+    const eventTypePage = await bookingPage.previewEventType();
+    await bookingPage.selectTimeSlot(eventTypePage);
+    await bookingPage.fillAllQuestions(eventTypePage, allQuestions, {
+      ...bookingOptions,
+      isAllRequired: 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 5fea0d62fa..72c8e44fea 100644
--- a/apps/web/playwright/fixtures/regularBookings.ts
+++ b/apps/web/playwright/fixtures/regularBookings.ts
@@ -15,6 +15,7 @@ type BookingOptions = {
   hasPlaceholder?: boolean;
   isReschedule?: boolean;
   isRequired?: boolean;
+  isAllRequired?: boolean;
   isMultiSelect?: boolean;
 };
 
@@ -116,6 +117,61 @@ const fillQuestion = async (eventTypePage: Page, questionType: string, customLoc
   }
 };
 
+const fillAllQuestions = async (eventTypePage: Page, questions: string[], options: BookingOptions) => {
+  if (options.isAllRequired) {
+    for (const question of questions) {
+      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(`${question} test`).check();
+          break;
+        case "multiemail":
+          await eventTypePage.getByRole("button", { name: "multiemail test" }).click();
+          await eventTypePage.getByPlaceholder("multiemail test").fill(EMAIL);
+          break;
+      }
+    }
+  }
+};
+
 export async function loginUser(users: UserFixture) {
   const pro = await users.create({ name: "testuser" });
   await pro.apiLogin();
@@ -282,5 +338,23 @@ export function createBookingPageFixture(page: Page) {
       await scheduleSuccessfullyPage.waitFor({ state: "visible" });
       await expect(scheduleSuccessfullyPage).toBeVisible();
     },
+    checkField: async (question: string) => {
+      await expect(page.getByTestId(`field-${question}-test`)).toBeVisible();
+    },
+    fillAllQuestions: async (eventTypePage: Page, questions: string[], options: BookingOptions) => {
+      const confirmButton = options.isReschedule ? "confirm-reschedule-button" : "confirm-book-button";
+      await fillAllQuestions(eventTypePage, questions, options);
+      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 fillAllQuestions(eventTypePage, questions, options);
+        await eventTypePage.getByTestId(confirmButton).click();
+      }
+      const scheduleSuccessfullyPage = eventTypePage.getByText(scheduleSuccessfullyText);
+      await scheduleSuccessfullyPage.waitFor({ state: "visible" });
+      await expect(scheduleSuccessfullyPage).toBeVisible();
+    },
   };
 }