diff --git a/apps/web/playwright/booking-pages.e2e.ts b/apps/web/playwright/booking-pages.e2e.ts
index 13dcbf8b0f7d4d..1531efbd66ce74 100644
--- a/apps/web/playwright/booking-pages.e2e.ts
+++ b/apps/web/playwright/booking-pages.e2e.ts
@@ -1,23 +1,23 @@
+import { WEBAPP_URL } from "@calcom/lib/constants";
+import { generateHashedLink } from "@calcom/lib/generateHashedLink";
+import { randomString } from "@calcom/lib/random";
+import { SchedulingType } from "@calcom/prisma/enums";
+import type { Schedule, TimeRange } from "@calcom/types/schedule";
+import { expect } from "@playwright/test";
+import { JSDOM } from "jsdom";
 import { test, todo } from "./lib/fixtures";
 import {
   bookFirstEvent,
   bookOptinEvent,
   bookTimeSlot,
+  cancelBookingFromBookingsList,
   confirmBooking,
   confirmReschedule,
   expectSlotNotAllowedToBook,
   selectFirstAvailableTimeSlotNextMonth,
   testEmail,
   testName,
-  cancelBookingFromBookingsList,
 } from "./lib/testUtils";
-import { WEBAPP_URL } from "@calcom/lib/constants";
-import { generateHashedLink } from "@calcom/lib/generateHashedLink";
-import { randomString } from "@calcom/lib/random";
-import { SchedulingType } from "@calcom/prisma/enums";
-import type { Schedule, TimeRange } from "@calcom/types/schedule";
-import { expect } from "@playwright/test";
-import { JSDOM } from "jsdom";
 
 const freeUserObj = { name: `Free-user-${randomString(3)}` };
 test.describe.configure({ mode: "parallel" });
@@ -486,8 +486,6 @@ test.describe("Booking on different layouts", () => {
 
     await page.click('[data-testid="toggle-group-item-column_view"]');
 
-    // Use the standard helper to select an available time slot next month
-    // This is more robust than manually clicking incrementMonth and reloading
     await selectFirstAvailableTimeSlotNextMonth(page);
 
     // Fill what is this meeting about? name email and notes
diff --git a/apps/web/playwright/lib/testUtils.ts b/apps/web/playwright/lib/testUtils.ts
index 9fff23a2552f2e..19ab2f8b6c2289 100644
--- a/apps/web/playwright/lib/testUtils.ts
+++ b/apps/web/playwright/lib/testUtils.ts
@@ -109,7 +109,22 @@ export async function selectFirstAvailableTimeSlotNextMonth(page: Page | Frame)
   // Wait for the booker to be ready before interacting
   const incrementMonth = page.getByTestId("incrementMonth");
   await incrementMonth.waitFor();
+
+  // Wait for the initial schedule data to load (available days rendered in date picker).
+  // This ensures the waitForResponse listener below only catches the month-change response,
+  // not the initial page load response. Without this, column view can race: stale time slots
+  // from the current month get clicked before the new month's schedule data arrives, causing
+  // the quick availability check to permanently disable the confirm button.
+  await page.locator('[data-testid="day"][data-disabled="false"]').nth(0).waitFor();
+
+  // Listen for the getSchedule response triggered by the month change.
+  // waitForResponse is only available on Page, not Frame.
+  const scheduleResponse =
+    "waitForResponse" in page
+      ? page.waitForResponse((resp) => resp.url().includes("getSchedule") && resp.status() === 200)
+      : Promise.resolve();
   await incrementMonth.click();
+  await scheduleResponse;
 
   // Wait for available day to appear after month increment
   const firstAvailableDay = page.locator('[data-testid="day"][data-disabled="false"]').nth(0);
@@ -125,7 +140,16 @@ export async function selectSecondAvailableTimeSlotNextMonth(page: Page) {
   // Wait for the booker to be ready before interacting
   const incrementMonth = page.getByTestId("incrementMonth");
   await incrementMonth.waitFor();
+
+  // Wait for initial schedule data to load before changing month (see selectFirstAvailableTimeSlotNextMonth)
+  await page.locator('[data-testid="day"][data-disabled="false"]').nth(0).waitFor();
+
+  // Listen for the getSchedule response triggered by the month change
+  const scheduleResponse = page.waitForResponse(
+    (resp) => resp.url().includes("getSchedule") && resp.status() === 200
+  );
   await incrementMonth.click();
+  await scheduleResponse;
 
   // Wait for available day to appear after month increment
   const secondAvailableDay = page.locator('[data-testid="day"][data-disabled="false"]').nth(1);