diff --git a/apps/web/components/eventtype/EventTypeSingleLayout.tsx b/apps/web/components/eventtype/EventTypeSingleLayout.tsx
index 38e22efcc7..ffeb9b4fa9 100644
--- a/apps/web/components/eventtype/EventTypeSingleLayout.tsx
+++ b/apps/web/components/eventtype/EventTypeSingleLayout.tsx
@@ -220,6 +220,7 @@ function EventTypeSingleLayout({
             <Tooltip content={t("preview")}>
               <Button
                 color="secondary"
+                data-testid="preview-button"
                 target="_blank"
                 variant="icon"
                 href={permalink}
diff --git a/apps/web/pages/booking/[uid].tsx b/apps/web/pages/booking/[uid].tsx
index dbc1071cce..469c1254fe 100644
--- a/apps/web/pages/booking/[uid].tsx
+++ b/apps/web/pages/booking/[uid].tsx
@@ -561,7 +561,12 @@ export default function Success(props: SuccessProps) {
                         <>
                           <div className="mt-9 font-medium">{label}</div>
                           <div className="col-span-2 mb-2 mt-9">
-                            <p className="break-words">{response.toString()}</p>
+                            <p
+                              className="break-words"
+                              data-testid="field-response"
+                              data-fob-field={field.name}>
+                              {response.toString()}
+                            </p>
                           </div>
                         </>
                       );
diff --git a/apps/web/playwright/fixtures/users.ts b/apps/web/playwright/fixtures/users.ts
index 8f0d55dad5..f53a4c58fb 100644
--- a/apps/web/playwright/fixtures/users.ts
+++ b/apps/web/playwright/fixtures/users.ts
@@ -44,9 +44,6 @@ const createTeamAndAddUser = async (
       slug: `team-${workerInfo.workerIndex}-${Date.now()}`,
     },
   });
-  if (!team) {
-    return;
-  }
 
   const { role = MembershipRole.OWNER, id: userId } = user;
   await prisma.membership.create({
@@ -54,8 +51,10 @@ const createTeamAndAddUser = async (
       teamId: team.id,
       userId,
       role: role,
+      accepted: true,
     },
   });
+  return team;
 };
 
 // creates a user fixture instance and stores the collection
@@ -246,7 +245,29 @@ export const createUsersFixture = (page: Page, workerInfo: WorkerInfo) => {
         include: userIncludes,
       });
       if (scenario.hasTeam) {
-        await createTeamAndAddUser({ user: { id: user.id, role: "OWNER" } }, workerInfo);
+        const team = await createTeamAndAddUser({ user: { id: user.id, role: "OWNER" } }, workerInfo);
+        await prisma.eventType.create({
+          data: {
+            team: {
+              connect: {
+                id: team.id,
+              },
+            },
+            users: {
+              connect: {
+                id: _user.id,
+              },
+            },
+            owner: {
+              connect: {
+                id: _user.id,
+              },
+            },
+            title: "Team Event - 30min",
+            slug: "team-event-30min",
+            length: 30,
+          },
+        });
       }
       const userFixture = createUserFixture(user, store.page!);
       store.users.push(userFixture);
diff --git a/apps/web/playwright/manage-booking-questions.e2e.ts b/apps/web/playwright/manage-booking-questions.e2e.ts
new file mode 100644
index 0000000000..9fd6ae42d8
--- /dev/null
+++ b/apps/web/playwright/manage-booking-questions.e2e.ts
@@ -0,0 +1,409 @@
+import type { Page, PlaywrightTestArgs } from "@playwright/test";
+import { expect } from "@playwright/test";
+import { WebhookTriggerEvents } from "@prisma/client";
+import type { createUsersFixture } from "playwright/fixtures/users";
+import { uuid } from "short-uuid";
+
+import prisma from "@calcom/prisma";
+
+import { test } from "./lib/fixtures";
+import { createHttpServer, waitFor, selectFirstAvailableTimeSlotNextMonth } from "./lib/testUtils";
+
+test.describe("Manage Booking Questions", () => {
+  test.afterEach(async ({ users }) => {
+    await users.deleteAll();
+  });
+
+  test.describe("For User EventType", () => {
+    test("Do a booking with a user added question and verify a few thing in b/w", async ({
+      page,
+      users,
+      context,
+    }, testInfo) => {
+      // Considering there are many steps in it, it would need more than default test timeout
+      test.setTimeout(testInfo.timeout * 3);
+      const user = await createAndLoginUserWithEventTypes({ users });
+
+      const webhookReceiver = await addWebhook(user);
+
+      await test.step("Go to EventType Page ", async () => {
+        const $eventTypes = page.locator("[data-testid=event-types] > li a");
+        const firstEventTypeElement = $eventTypes.first();
+
+        await firstEventTypeElement.click();
+      });
+
+      await test.step("Add Question and see that it's shown on Booking Page at appropriate position", async () => {
+        await addQuestionAndSave({
+          page,
+          question: {
+            name: "how_are_you",
+            type: "Name",
+            label: "How are you?",
+            placeholder: "I'm fine, thanks",
+            required: true,
+          },
+        });
+
+        await doOnFreshPreview(page, context, async (page) => {
+          const allFieldsLocator = await expectSystemFieldsToBeThere(page);
+          const userFieldLocator = allFieldsLocator.nth(5);
+
+          await expect(userFieldLocator.locator('[name="how_are_you"]')).toBeVisible();
+          // There are 2 labels right now. Will be one in future. The second one is hidden
+          expect(await userFieldLocator.locator("label").nth(0).innerText()).toBe("How are you?");
+          await expect(userFieldLocator.locator("input[type=text]")).toBeVisible();
+        });
+      });
+
+      await test.step("Hide Question and see that it's not shown on Booking Page", async () => {
+        await toggleQuestionAndSave({
+          name: "how_are_you",
+          page,
+        });
+        await doOnFreshPreview(page, context, async (page) => {
+          const formBuilderFieldLocator = page.locator('[data-fob-field-name="how_are_you"]');
+          await expect(formBuilderFieldLocator).toBeHidden();
+        });
+      });
+
+      await test.step("Show Question Again", async () => {
+        await toggleQuestionAndSave({
+          name: "how_are_you",
+          page,
+        });
+      });
+
+      await test.step('Try to book without providing "How are you?" response', async () => {
+        await doOnFreshPreview(page, context, async (page) => {
+          await bookTimeSlot({ page, name: "Booker", email: "booker@example.com" });
+          await expectErrorToBeThereFor({ page, name: "how_are_you" });
+        });
+      });
+
+      await test.step("Do a booking", async () => {
+        await doOnFreshPreview(page, context, async (page) => {
+          const formBuilderFieldLocator = page.locator('[data-fob-field-name="how_are_you"]');
+          await expect(formBuilderFieldLocator).toBeVisible();
+          expect(
+            await formBuilderFieldLocator.locator('[name="how_are_you"]').getAttribute("placeholder")
+          ).toBe("I'm fine, thanks");
+          expect(await formBuilderFieldLocator.locator("label").nth(0).innerText()).toBe("How are you?");
+          await formBuilderFieldLocator.locator('[name="how_are_you"]').fill("I am great!");
+          await bookTimeSlot({ page, name: "Booker", email: "booker@example.com" });
+          await expect(page.locator("[data-testid=success-page]")).toBeVisible();
+
+          expect(
+            await page.locator('[data-testid="field-response"][data-fob-field="how_are_you"]').innerText()
+          ).toBe("I am great!");
+
+          await waitFor(() => {
+            expect(webhookReceiver.requestList.length).toBe(1);
+          });
+
+          const [request] = webhookReceiver.requestList;
+
+          const payload = (request.body as any).payload as any;
+
+          expect(payload.responses).toMatchObject({
+            name: "Booker",
+            email: "booker@example.com",
+            how_are_you: "I am great!",
+          });
+
+          expect(payload.location).toBe("integrations:daily");
+
+          expect(payload.attendees[0]).toMatchObject({
+            name: "Booker",
+            email: "booker@example.com",
+          });
+
+          expect(payload.userFieldsResponses).toMatchObject({
+            how_are_you: "I am great!",
+          });
+        });
+      });
+    });
+  });
+
+  test.describe("For Team EventType", () => {
+    test("Do a booking with a user added question and verify a few thing in b/w", async ({
+      page,
+      users,
+      context,
+    }, testInfo) => {
+      // Considering there are many steps in it, it would need more than default test timeout
+      test.setTimeout(testInfo.timeout * 3);
+      const user = await createAndLoginUserWithEventTypes({ users });
+
+      const webhookReceiver = await addWebhook(user);
+
+      await test.step("Go to First Team Event", async () => {
+        const $eventTypes = page.locator("[data-testid=event-types]").nth(1).locator("li a");
+        const firstEventTypeElement = $eventTypes.first();
+
+        await firstEventTypeElement.click();
+      });
+
+      await runTestStepsCommonForTeamAndUserEventType(page, context, webhookReceiver);
+    });
+  });
+});
+
+async function runTestStepsCommonForTeamAndUserEventType(
+  page: Page,
+  context: PlaywrightTestArgs["context"],
+  webhookReceiver: {
+    port: number;
+    close: () => import("http").Server;
+    requestList: (import("http").IncomingMessage & { body?: unknown })[];
+    url: string;
+  }
+) {
+  await test.step("Add Question and see that it's shown on Booking Page at appropriate position", async () => {
+    await addQuestionAndSave({
+      page,
+      question: {
+        name: "how_are_you",
+        type: "Name",
+        label: "How are you?",
+        placeholder: "I'm fine, thanks",
+        required: true,
+      },
+    });
+
+    await doOnFreshPreview(page, context, async (page) => {
+      const allFieldsLocator = await expectSystemFieldsToBeThere(page);
+      const userFieldLocator = allFieldsLocator.nth(5);
+
+      await expect(userFieldLocator.locator('[name="how_are_you"]')).toBeVisible();
+      // There are 2 labels right now. Will be one in future. The second one is hidden
+      expect(await userFieldLocator.locator("label").nth(0).innerText()).toBe("How are you?");
+      await expect(userFieldLocator.locator("input[type=text]")).toBeVisible();
+    });
+  });
+
+  await test.step("Hide Question and see that it's not shown on Booking Page", async () => {
+    await toggleQuestionAndSave({
+      name: "how_are_you",
+      page,
+    });
+    await doOnFreshPreview(page, context, async (page) => {
+      const formBuilderFieldLocator = page.locator('[data-fob-field-name="how_are_you"]');
+      await expect(formBuilderFieldLocator).toBeHidden();
+    });
+  });
+
+  await test.step("Show Question Again", async () => {
+    await toggleQuestionAndSave({
+      name: "how_are_you",
+      page,
+    });
+  });
+
+  await test.step('Try to book without providing "How are you?" response', async () => {
+    await doOnFreshPreview(page, context, async (page) => {
+      await bookTimeSlot({ page, name: "Booker", email: "booker@example.com" });
+      await expectErrorToBeThereFor({ page, name: "how_are_you" });
+    });
+  });
+
+  await test.step("Do a booking", async () => {
+    await doOnFreshPreview(page, context, async (page) => {
+      const formBuilderFieldLocator = page.locator('[data-fob-field-name="how_are_you"]');
+      await expect(formBuilderFieldLocator).toBeVisible();
+      expect(await formBuilderFieldLocator.locator('[name="how_are_you"]').getAttribute("placeholder")).toBe(
+        "I'm fine, thanks"
+      );
+      expect(await formBuilderFieldLocator.locator("label").nth(0).innerText()).toBe("How are you?");
+      await formBuilderFieldLocator.locator('[name="how_are_you"]').fill("I am great!");
+      await bookTimeSlot({ page, name: "Booker", email: "booker@example.com" });
+      await expect(page.locator("[data-testid=success-page]")).toBeVisible();
+
+      expect(
+        await page.locator('[data-testid="field-response"][data-fob-field="how_are_you"]').innerText()
+      ).toBe("I am great!");
+
+      await waitFor(() => {
+        expect(webhookReceiver.requestList.length).toBe(1);
+      });
+
+      const [request] = webhookReceiver.requestList;
+
+      const payload = (request.body as any).payload as any;
+
+      expect(payload.responses).toMatchObject({
+        name: "Booker",
+        email: "booker@example.com",
+        how_are_you: "I am great!",
+      });
+
+      expect(payload.location).toBe("integrations:daily");
+
+      expect(payload.attendees[0]).toMatchObject({
+        name: "Booker",
+        email: "booker@example.com",
+      });
+
+      expect(payload.userFieldsResponses).toMatchObject({
+        how_are_you: "I am great!",
+      });
+    });
+  });
+}
+
+async function expectSystemFieldsToBeThere(page: Page) {
+  const allFieldsLocator = page.locator("[data-fob-field-name]:not(.hidden)");
+  const nameLocator = allFieldsLocator.nth(0);
+  const emailLocator = allFieldsLocator.nth(1);
+  // Location isn't rendered unless explicitly set which isn't the case here
+  // const locationLocator = allFieldsLocator.nth(2);
+  const additionalNotes = allFieldsLocator.nth(3);
+  const guestsLocator = allFieldsLocator.nth(4);
+
+  await expect(nameLocator.locator('[name="name"]')).toBeVisible();
+  await expect(emailLocator.locator('[name="email"]')).toBeVisible();
+
+  await expect(additionalNotes.locator('[name="notes"]')).toBeVisible();
+  await expect(guestsLocator.locator("button")).toBeVisible();
+  return allFieldsLocator;
+}
+
+//TODO: Add one question for each type and see they are rendering labels and only once and are showing appropriate native component
+// Verify webhook is sent with the correct data, DB is correct (including metadata)
+
+//TODO: Verify that prefill works
+async function bookTimeSlot({ page, name, email }: { page: Page; name: string; email: string }) {
+  // --- fill form
+  await page.fill('[name="name"]', name);
+  await page.fill('[name="email"]', email);
+  await page.press('[name="email"]', "Enter");
+}
+/**
+ * 'option' starts from 1
+ */
+async function selectOption({
+  page,
+  selector,
+  optionText,
+}: {
+  page: Page;
+  selector: { selector: string; nth: number };
+  optionText: string;
+}) {
+  const locatorForSelect = page.locator(selector.selector).nth(selector.nth);
+  await locatorForSelect.click();
+  await locatorForSelect.locator(`text="${optionText}"`).click();
+}
+
+async function addQuestionAndSave({
+  page,
+  question,
+}: {
+  page: Page;
+  question: {
+    name?: string;
+    type?: string;
+    label?: string;
+    placeholder?: string;
+    required?: boolean;
+  };
+}) {
+  await page.click('[href$="tabName=advanced"]');
+  await page.click('[data-testid="add-field"]');
+
+  if (question.type !== undefined) {
+    await selectOption({
+      page,
+      selector: {
+        selector: "[id=test-field-type]",
+        nth: 0,
+      },
+      optionText: question.type,
+    });
+  }
+
+  if (question.name !== undefined) {
+    await page.fill('[name="name"]', question.name);
+  }
+
+  if (question.label !== undefined) {
+    await page.fill('[name="label"]', question.label);
+  }
+
+  if (question.placeholder !== undefined) {
+    await page.fill('[name="placeholder"]', question.placeholder);
+  }
+
+  if (question.required !== undefined) {
+    // await page.fill('[name="name"]', question.required);
+  }
+
+  await page.click('[data-testid="field-add-save"]');
+  await saveEventType(page);
+}
+
+async function expectErrorToBeThereFor({ page, name }: { page: Page; name: string }) {
+  await expect(page.locator(`[data-testid=error-message-${name}]`)).toHaveCount(1);
+  // TODO: We should either verify the error message or error code in the test so we know that the correct error is shown
+  // Checking for the error message isn't well maintainable as translation can change and we might want to verify in non english language as well.
+}
+
+/**
+ * Opens a fresh preview window and runs the callback on it giving it the preview tab's `page`
+ */
+async function doOnFreshPreview(
+  page: Page,
+  context: PlaywrightTestArgs["context"],
+  callback: (page: Page) => Promise<void>
+) {
+  const previewTabPage = await openBookingFormInPreviewTab(context, page);
+  await callback(previewTabPage);
+  await previewTabPage.close();
+}
+
+async function toggleQuestionAndSave({ name, page }: { name: string; page: Page }) {
+  await page.locator(`[data-testid="field-${name}"]`).locator('[data-testid="toggle-field"]').click();
+  await saveEventType(page);
+}
+
+async function createAndLoginUserWithEventTypes({ users }: { users: ReturnType<typeof createUsersFixture> }) {
+  const user = await users.create(null, {
+    hasTeam: true,
+  });
+  await user.login();
+  return user;
+}
+
+async function openBookingFormInPreviewTab(context: PlaywrightTestArgs["context"], page: Page) {
+  const previewTabPromise = context.waitForEvent("page");
+  await page.locator('[data-testid="preview-button"]').click();
+  const previewTabPage = await previewTabPromise;
+  await previewTabPage.waitForLoadState();
+  await selectFirstAvailableTimeSlotNextMonth(previewTabPage);
+  await previewTabPage.waitForNavigation({
+    url: (url) => url.pathname.endsWith("/book"),
+  });
+  return previewTabPage;
+}
+
+async function saveEventType(page: Page) {
+  await page.locator("[data-testid=update-eventtype]").click();
+}
+
+async function addWebhook(user: Awaited<ReturnType<typeof createAndLoginUserWithEventTypes>>) {
+  const webhookReceiver = createHttpServer();
+  await prisma.webhook.create({
+    data: {
+      id: uuid(),
+      userId: user.id,
+      subscriberUrl: webhookReceiver.url,
+      eventTriggers: [
+        WebhookTriggerEvents.BOOKING_CREATED,
+        WebhookTriggerEvents.BOOKING_CANCELLED,
+        WebhookTriggerEvents.BOOKING_RESCHEDULED,
+      ],
+    },
+  });
+  return webhookReceiver;
+}
diff --git a/packages/features/form-builder/FormBuilder.tsx b/packages/features/form-builder/FormBuilder.tsx
index 3c909d354d..6cdaaf5603 100644
--- a/packages/features/form-builder/FormBuilder.tsx
+++ b/packages/features/form-builder/FormBuilder.tsx
@@ -286,6 +286,7 @@ export const FormBuilder = function FormBuilder({
             return (
               <li
                 key={index}
+                data-testid={`field-${field.name}`}
                 className="group relative flex items-center justify-between border-b p-4 last:border-b-0">
                 <button
                   type="button"
@@ -322,6 +323,7 @@ export const FormBuilder = function FormBuilder({
                 {field.editable !== "user-readonly" && (
                   <div className="flex items-center space-x-2">
                     <Switch
+                      data-testid="toggle-field"
                       disabled={field.editable === "system"}
                       tooltip={field.editable === "system" ? t("form_builder_system_field_cant_toggle") : ""}
                       checked={!field.hidden}
@@ -356,7 +358,12 @@ export const FormBuilder = function FormBuilder({
             );
           })}
         </ul>
-        <Button color="minimal" onClick={addField} className="mt-4" StartIcon={FiPlus}>
+        <Button
+          color="minimal"
+          data-testid="add-field"
+          onClick={addField}
+          className="mt-4"
+          StartIcon={FiPlus}>
           {addFieldLabel}
         </Button>
       </div>
@@ -405,6 +412,7 @@ export const FormBuilder = function FormBuilder({
               }}>
               <SelectField
                 defaultValue={FieldTypes[3]} // "text" as defaultValue
+                id="test-field-type"
                 isDisabled={
                   fieldForm.getValues("editable") === "system" ||
                   fieldForm.getValues("editable") === "system-but-optional"
@@ -473,7 +481,9 @@ export const FormBuilder = function FormBuilder({
               />
               <DialogFooter>
                 <DialogClose color="secondary">Cancel</DialogClose>
-                <Button type="submit">{isFieldEditMode ? t("save") : t("add")}</Button>
+                <Button data-testid="field-add-save" type="submit">
+                  {isFieldEditMode ? t("save") : t("add")}
+                </Button>
               </DialogFooter>
             </Form>
           </div>
@@ -684,9 +694,7 @@ export const FormBuilderField = ({
   const { t } = useLocale();
   const { control, formState } = useFormContext();
   return (
-    <div
-      data-form-builder-field-name={field.name}
-      className={classNames(className, field.hidden ? "hidden" : "")}>
+    <div data-fob-field-name={field.name} className={classNames(className, field.hidden ? "hidden" : "")}>
       <Controller
         control={control}
         // Make it a variable
@@ -718,7 +726,7 @@ export const FormBuilderField = ({
                   }
                   return (
                     <div
-                      data-field-name={field.name}
+                      data-testid={`error-message-${field.name}`}
                       className="mt-2 flex items-center text-sm text-red-700 ">
                       <FiInfo className="h-3 w-3 ltr:mr-2 rtl:ml-2" />
                       <p>{t(message)}</p>
diff --git a/playwright.config.ts b/playwright.config.ts
index fb03d86ecc..52b74adad4 100644
--- a/playwright.config.ts
+++ b/playwright.config.ts
@@ -8,7 +8,15 @@ dotEnv.config({ path: ".env" });
 
 const outputDir = path.join(__dirname, "test-results");
 
-const DEFAULT_NAVIGATION_TIMEOUT = 15000;
+// Dev Server on local can be slow to start up and process requests. So, keep timeouts really high on local, so that tests run reliably locally
+
+// So, if not in CI, keep the timers high, if the test is stuck somewhere and there is unnecessary wait developer can see in browser that it's stuck
+const DEFAULT_NAVIGATION_TIMEOUT = process.env.CI ? 15000 : 50000;
+const DEFAULT_EXPECT_TIMEOUT = process.env.CI ? 10000 : 50000;
+
+// Test Timeout can hit due to slow expect, slow navigation.
+// So, it should me much higher than sum of expect and navigation timeouts as there can be many async expects and navigations in a single test
+const DEFAULT_TEST_TIMEOUT = process.env.CI ? 60000 : 120000;
 
 const headless = !!process.env.CI || !!process.env.PLAYWRIGHT_HEADLESS;
 
@@ -36,7 +44,7 @@ const config: PlaywrightTestConfig = {
   forbidOnly: !!process.env.CI,
   retries: 2,
   workers: os.cpus().length,
-  timeout: 60_000,
+  timeout: DEFAULT_TEST_TIMEOUT,
   maxFailures: headless ? 10 : undefined,
   fullyParallel: true,
   reporter: [
@@ -58,6 +66,9 @@ const config: PlaywrightTestConfig = {
       name: "@calcom/web",
       testDir: "./apps/web/playwright",
       testMatch: /.*\.e2e\.tsx?/,
+      expect: {
+        timeout: DEFAULT_EXPECT_TIMEOUT,
+      },
       use: {
         ...devices["Desktop Chrome"],
         /** If navigation takes more than this, then something's wrong, let's fail fast. */
@@ -68,6 +79,9 @@ const config: PlaywrightTestConfig = {
       name: "@calcom/app-store",
       testDir: "./packages/app-store/",
       testMatch: /.*\.e2e\.tsx?/,
+      expect: {
+        timeout: DEFAULT_EXPECT_TIMEOUT,
+      },
       use: {
         ...devices["Desktop Chrome"],
         /** If navigation takes more than this, then something's wrong, let's fail fast. */