diff --git a/apps/web/playwright/fixtures/regularBookings.ts b/apps/web/playwright/fixtures/regularBookings.ts
index 2c49c276a9..2f380057af 100644
--- a/apps/web/playwright/fixtures/regularBookings.ts
+++ b/apps/web/playwright/fixtures/regularBookings.ts
@@ -110,6 +110,61 @@ 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();
@@ -195,6 +250,14 @@ 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(400);
+      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) => {
@@ -258,63 +321,15 @@ export function createBookingPageFixture(page: Page) {
     },
     fillAllQuestions: 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) {
-          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;
-          }
-        }
-      }
-
+      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();