diff --git a/apps/web/playwright/fixtures/regularBookings.ts b/apps/web/playwright/fixtures/regularBookings.ts
index 5bd9d80c3a..c65568723f 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(200);
+      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(200);
+      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();