diff --git a/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts b/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts
index eda08dacd3..e40a514961 100644
--- a/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts
+++ b/apps/web/playwright/booking/checkboxGroupQuestion.e2e.ts
@@ -52,7 +52,7 @@ test.describe("Booking With Checkbox Group Question and Each Other Question", ()
       await bookingPage.assertBookingCanceled(eventTypePage);
     });
 
-    test.describe("Booking With Checkbox Group Question and checkbox group Question", () => {
+    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");
diff --git a/apps/web/playwright/fixtures/regularBookings.ts b/apps/web/playwright/fixtures/regularBookings.ts
index 5bd9d80c3a..06b00a22a6 100644
--- a/apps/web/playwright/fixtures/regularBookings.ts
+++ b/apps/web/playwright/fixtures/regularBookings.ts
@@ -194,6 +194,14 @@ 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(100);
+      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) => {
@@ -248,6 +256,14 @@ export function createBookingPageFixture(page: Page) {
       options.isRequired && (await fillQuestion(eventTypePage, secondQuestion, customLocators));
 
       await eventTypePage.getByTestId(confirmButton).click();
+      await eventTypePage.waitForTimeout(100);
+      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();