diff --git a/apps/web/components/booking/pages/BookingPage.tsx b/apps/web/components/booking/pages/BookingPage.tsx
index c0f8ebf10f..c2cf64523a 100644
--- a/apps/web/components/booking/pages/BookingPage.tsx
+++ b/apps/web/components/booking/pages/BookingPage.tsx
@@ -540,7 +540,9 @@ const BookingPage = (props: BookingPageProps) => {
                   </div>
                 </Form>
                 {mutation.isError && (
-                  <div className="mt-2 border-l-4 border-yellow-400 bg-yellow-50 p-4">
+                  <div
+                    data-testid="booking-fail"
+                    className="mt-2 border-l-4 border-yellow-400 bg-yellow-50 p-4">
                     <div className="flex">
                       <div className="flex-shrink-0">
                         <ExclamationIcon className="h-5 w-5 text-yellow-400" aria-hidden="true" />
diff --git a/apps/web/pages/api/book/event.ts b/apps/web/pages/api/book/event.ts
index f448591a2f..f6c8f59846 100644
--- a/apps/web/pages/api/book/event.ts
+++ b/apps/web/pages/api/book/event.ts
@@ -21,6 +21,7 @@ import { getErrorFromUnknown } from "@lib/errors";
 import { getEventName } from "@lib/event";
 import EventManager, { EventResult, PartialReference } from "@lib/events/EventManager";
 import { getBusyCalendarTimes } from "@lib/integrations/calendar/CalendarManager";
+import { EventBusyDate } from "@lib/integrations/calendar/constants/types";
 import { CalendarEvent, AdditionInformation } from "@lib/integrations/calendar/interfaces/Calendar";
 import { BufferedBusyTime } from "@lib/integrations/calendar/interfaces/Office365Calendar";
 import logger from "@lib/logger";
@@ -408,27 +409,11 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     });
   }
 
-  type Booking = Prisma.PromiseReturnType<typeof createBooking>;
-  let booking: Booking | null = null;
-  try {
-    booking = await createBooking();
-    evt.uid = booking.uid;
-  } catch (_err) {
-    const err = getErrorFromUnknown(_err);
-    log.error(`Booking ${eventTypeId} failed`, "Error when saving booking to db", err.message);
-    if (err.code === "P2002") {
-      res.status(409).json({ message: "booking.conflict" });
-      return;
-    }
-    res.status(500).end();
-    return;
-  }
-
   let results: EventResult[] = [];
   let referencesToCreate: PartialReference[] = [];
   let user: User | null = null;
 
-  /** Let's start cheking for availability */
+  /** Let's start checking for availability */
   for (const currentUser of users) {
     if (!currentUser) {
       console.error(`currentUser not found`);
@@ -443,68 +428,94 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     });
 
     const credentials = currentUser.credentials;
+    const calendarBusyTimes: EventBusyDate[] = await prisma.booking
+      .findMany({
+        where: {
+          userId: currentUser.id,
+          eventTypeId: eventTypeId,
+        },
+      })
+      .then((bookings) => bookings.map((booking) => ({ end: booking.endTime, start: booking.startTime })));
+
     if (credentials) {
-      const calendarBusyTimes = await getBusyCalendarTimes(
-        credentials,
-        reqBody.start,
-        reqBody.end,
-        selectedCalendars
+      await getBusyCalendarTimes(credentials, reqBody.start, reqBody.end, selectedCalendars).then(
+        (busyTimes) => calendarBusyTimes.push(...busyTimes)
       );
 
       const videoBusyTimes = (await getBusyVideoTimes(credentials)).filter(notEmpty);
       calendarBusyTimes.push(...videoBusyTimes);
-      console.log("calendarBusyTimes==>>>", calendarBusyTimes);
-
-      const bufferedBusyTimes: BufferedBusyTimes = calendarBusyTimes.map((a) => ({
-        start: dayjs(a.start).subtract(currentUser.bufferTime, "minute").toString(),
-        end: dayjs(a.end).add(currentUser.bufferTime, "minute").toString(),
-      }));
-
-      let isAvailableToBeBooked = true;
-      try {
-        isAvailableToBeBooked = isAvailable(bufferedBusyTimes, reqBody.start, eventType.length);
-      } catch {
-        log.debug({
-          message: "Unable set isAvailableToBeBooked. Using true. ",
-        });
-      }
-
-      if (!isAvailableToBeBooked) {
-        const error = {
-          errorCode: "BookingUserUnAvailable",
-          message: `${currentUser.name} is unavailable at this time.`,
-        };
-
-        log.debug(`Booking ${currentUser.name} failed`, error);
-      }
-
-      let timeOutOfBounds = false;
-
-      try {
-        timeOutOfBounds = isOutOfBounds(reqBody.start, {
-          periodType: eventType.periodType,
-          periodDays: eventType.periodDays,
-          periodEndDate: eventType.periodEndDate,
-          periodStartDate: eventType.periodStartDate,
-          periodCountCalendarDays: eventType.periodCountCalendarDays,
-          timeZone: currentUser.timeZone,
-        });
-      } catch {
-        log.debug({
-          message: "Unable set timeOutOfBounds. Using false. ",
-        });
-      }
-
-      if (timeOutOfBounds) {
-        const error = {
-          errorCode: "BookingUserUnAvailable",
-          message: `${currentUser.name} is unavailable at this time.`,
-        };
-
-        log.debug(`Booking ${currentUser.name} failed`, error);
-        res.status(400).json(error);
-      }
     }
+
+    console.log("calendarBusyTimes==>>>", calendarBusyTimes);
+
+    const bufferedBusyTimes: BufferedBusyTimes = calendarBusyTimes.map((a) => ({
+      start: dayjs(a.start).subtract(currentUser.bufferTime, "minute").toString(),
+      end: dayjs(a.end).add(currentUser.bufferTime, "minute").toString(),
+    }));
+
+    let isAvailableToBeBooked = true;
+    try {
+      isAvailableToBeBooked = isAvailable(bufferedBusyTimes, reqBody.start, eventType.length);
+    } catch {
+      log.debug({
+        message: "Unable set isAvailableToBeBooked. Using true. ",
+      });
+    }
+
+    if (!isAvailableToBeBooked) {
+      const error = {
+        errorCode: "BookingUserUnAvailable",
+        message: `${currentUser.name} is unavailable at this time.`,
+      };
+
+      log.debug(`Booking ${currentUser.name} failed`, error);
+      res.status(409).json(error);
+      return;
+    }
+
+    let timeOutOfBounds = false;
+
+    try {
+      timeOutOfBounds = isOutOfBounds(reqBody.start, {
+        periodType: eventType.periodType,
+        periodDays: eventType.periodDays,
+        periodEndDate: eventType.periodEndDate,
+        periodStartDate: eventType.periodStartDate,
+        periodCountCalendarDays: eventType.periodCountCalendarDays,
+        timeZone: currentUser.timeZone,
+      });
+    } catch {
+      log.debug({
+        message: "Unable set timeOutOfBounds. Using false. ",
+      });
+    }
+
+    if (timeOutOfBounds) {
+      const error = {
+        errorCode: "BookingUserUnAvailable",
+        message: `${currentUser.name} is unavailable at this time.`,
+      };
+
+      log.debug(`Booking ${currentUser.name} failed`, error);
+      res.status(400).json(error);
+      return;
+    }
+  }
+
+  type Booking = Prisma.PromiseReturnType<typeof createBooking>;
+  let booking: Booking | null = null;
+  try {
+    booking = await createBooking();
+    evt.uid = booking.uid;
+  } catch (_err) {
+    const err = getErrorFromUnknown(_err);
+    log.error(`Booking ${eventTypeId} failed`, "Error when saving booking to db", err.message);
+    if (err.code === "P2002") {
+      res.status(409).json({ message: "booking.conflict" });
+      return;
+    }
+    res.status(500).end();
+    return;
   }
 
   if (!user) throw Error("Can't continue, user not found.");
diff --git a/apps/web/playwright/booking-pages.test.ts b/apps/web/playwright/booking-pages.test.ts
index 0e365ef606..f9efb7540b 100644
--- a/apps/web/playwright/booking-pages.test.ts
+++ b/apps/web/playwright/booking-pages.test.ts
@@ -1,16 +1,80 @@
 import { expect, test } from "@playwright/test";
 
+import prisma from "@lib/prisma";
+
 import { todo } from "./lib/testUtils";
 
+const deleteBookingsByEmail = async (email: string) =>
+  prisma.booking.deleteMany({
+    where: {
+      user: {
+        email,
+      },
+    },
+  });
+
 test.describe("free user", () => {
   test.beforeEach(async ({ page }) => {
     await page.goto("/free");
   });
+
+  test.afterEach(async () => {
+    // delete test bookings
+    await deleteBookingsByEmail("free@example.com");
+  });
+
   test("only one visible event", async ({ page }) => {
     await expect(page.locator(`[href="/free/30min"]`)).toBeVisible();
     await expect(page.locator(`[href="/free/60min"]`)).not.toBeVisible();
   });
 
+  test("cannot book same slot multiple times", async ({ page }) => {
+    // Click first event type
+    await page.click('[data-testid="event-type-link"]');
+    // Click [data-testid="incrementMonth"]
+    await page.click('[data-testid="incrementMonth"]');
+    // Click [data-testid="day"]
+    await page.click('[data-testid="day"][data-disabled="false"]');
+    // Click [data-testid="time"]
+    await page.click('[data-testid="time"]');
+
+    // Navigate to book page
+    await page.waitForNavigation({
+      url(url) {
+        return url.pathname.endsWith("/book");
+      },
+    });
+
+    // save booking url
+    const bookingUrl: string = page.url();
+
+    const bookTimeSlot = async () => {
+      // --- fill form
+      await page.fill('[name="name"]', "Test Testson");
+      await page.fill('[name="email"]', "test@example.com");
+      await page.press('[name="email"]', "Enter");
+    };
+
+    // book same time spot twice
+    await bookTimeSlot();
+
+    // Make sure we're navigated to the success page
+    await page.waitForNavigation({
+      url(url) {
+        return url.pathname.endsWith("/success");
+      },
+    });
+
+    // return to same time spot booking page
+    await page.goto(bookingUrl);
+
+    // book same time spot again
+    await bookTimeSlot();
+
+    // check for error message
+    await expect(page.locator("[data-testid=booking-fail]")).toBeVisible();
+  });
+
   todo("`/free/30min` is bookable");
 
   todo("`/free/60min` is not bookable");
@@ -21,6 +85,11 @@ test.describe("pro user", () => {
     await page.goto("/pro");
   });
 
+  test.afterEach(async () => {
+    // delete test bookings
+    await deleteBookingsByEmail("pro@example.com");
+  });
+
   test("pro user's page has at least 2 visible events", async ({ page }) => {
     const $eventTypes = await page.$$("[data-testid=event-types] > *");
     expect($eventTypes.length).toBeGreaterThanOrEqual(2);
diff --git a/yarn.lock b/yarn.lock
index ab67685c24..5f6d55bcbe 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -1012,7 +1012,12 @@
   resolved "https://registry.yarnpkg.com/@headlessui/react/-/react-1.4.3.tgz#f77c6bb5cb4a614a5d730fb880cab502d48abf37"
   integrity sha512-n2IQkaaw0aAAlQS5MEXsM4uRK+w18CrM72EqnGRl/UBOQeQajad8oiKXR9Nk15jOzTFQjpxzrZMf1NxHidFBiw==
 
-"@heroicons/react@^1.0.4", "@heroicons/react@^1.0.5":
+"@heroicons/react@^1.0.4":
+  version "1.0.6"
+  resolved "https://registry.yarnpkg.com/@heroicons/react/-/react-1.0.6.tgz#35dd26987228b39ef2316db3b1245c42eb19e324"
+  integrity sha512-JJCXydOFWMDpCP4q13iEplA503MQO3xLoZiKum+955ZCtHINWnx26CUxVxxFQu/uLb4LW3ge15ZpzIkXKkJ8oQ==
+
+"@heroicons/react@^1.0.5":
   version "1.0.5"
   resolved "https://registry.yarnpkg.com/@heroicons/react/-/react-1.0.5.tgz#2fe4df9d33eb6ce6d5178a0f862e97b61c01e27d"
   integrity sha512-UDMyLM2KavIu2vlWfMspapw9yii7aoLwzI2Hudx4fyoPwfKfxU8r3cL8dEBXOjcLG0/oOONZzbT14M1HoNtEcg==
@@ -2590,9 +2595,9 @@
   integrity sha512-fm8TR8r4LwbXgBIYdPmeMjJJkxxFC66tvoliNnmXOpUgZSgQKoNPW3ON0ZphZIiif1oqWNhAaSrr7tOvGu+AFg==
 
 "@stripe/stripe-js@^1.17.1":
-  version "1.23.0"
-  resolved "https://registry.yarnpkg.com/@stripe/stripe-js/-/stripe-js-1.23.0.tgz#62eed14e83c63c3e8c27f14f6b1e6feb8496c867"
-  integrity sha512-+7w4rVs71Fk8/8uzyzQB5GotHSH9mjOjxM3EYDq/3MR3I2ewELHtvWVMOqfS/9WSKCaKv7h7eFLsMZGpK5jApQ==
+  version "1.24.0"
+  resolved "https://registry.yarnpkg.com/@stripe/stripe-js/-/stripe-js-1.24.0.tgz#d23977f364565981f8ab30b1b540e367f72abc5c"
+  integrity sha512-8CEILOpzoRhGwvgcf6y+BlPyEq1ZqxAv3gsX7LvokFYvbcyH72GRcHQMGXuZS3s7HqfYQuTSFrvZNL/qdkgA9Q==
 
 "@szmarczak/http-timer@^1.1.2":
   version "1.1.2"
@@ -5072,11 +5077,16 @@ dayjs-business-time@^1.0.4:
   dependencies:
     dayjs "^1.10.4"
 
-dayjs@^1.10.4, dayjs@^1.10.6, dayjs@^1.10.7:
+dayjs@^1.10.4, dayjs@^1.10.6:
   version "1.10.7"
   resolved "https://registry.yarnpkg.com/dayjs/-/dayjs-1.10.7.tgz#2cf5f91add28116748440866a0a1d26f3a6ce468"
   integrity sha512-P6twpd70BcPK34K26uJ1KT3wlhpuOAPoMwJzpsIWUxHZ7wpmbdZL/hQqBDfz7hGurYSa5PhzdhDHtt319hL3ig==
 
+dayjs@^1.10.7:
+  version "1.10.8"
+  resolved "https://registry.yarnpkg.com/dayjs/-/dayjs-1.10.8.tgz#267df4bc6276fcb33c04a6735287e3f429abec41"
+  integrity sha512-wbNwDfBHHur9UOzNUjeKUOJ0fCb0a52Wx0xInmQ7Y8FstyajiV1NmK1e00cxsr9YrE9r7yAChE0VvpuY5Rnlow==
+
 debug@2.6.9, debug@^2.2.0, debug@^2.3.3, debug@^2.6.9:
   version "2.6.9"
   resolved "https://registry.yarnpkg.com/debug/-/debug-2.6.9.tgz#5d128515df134ff327e90a4c93f4e077a536341f"
@@ -11520,9 +11530,9 @@ postcss@8.4.5:
     source-map-js "^1.0.1"
 
 postcss@^8.1.6, postcss@^8.3.5, postcss@^8.3.6:
-  version "8.4.7"
-  resolved "https://registry.yarnpkg.com/postcss/-/postcss-8.4.7.tgz#f99862069ec4541de386bf57f5660a6c7a0875a8"
-  integrity sha512-L9Ye3r6hkkCeOETQX6iOaWZgjp3LL6Lpqm6EtgbKrgqGGteRMNb9vzBfRL96YOSu8o7x3MfIH9Mo5cPJFGrW6A==
+  version "8.4.8"
+  resolved "https://registry.yarnpkg.com/postcss/-/postcss-8.4.8.tgz#dad963a76e82c081a0657d3a2f3602ce10c2e032"
+  integrity sha512-2tXEqGxrjvAO6U+CJzDL2Fk2kPHTv1jQsYkSoMeOis2SsYaXRO2COxTdQp99cYvif9JTXaAk9lYGc3VhJt7JPQ==
   dependencies:
     nanoid "^3.3.1"
     picocolors "^1.0.0"
@@ -15400,9 +15410,9 @@ zod@^3.8.2:
   integrity sha512-daZ80A81I3/9lIydI44motWe6n59kRBfNzTuS2bfzVh1nAXi667TOTWWtatxyG+fwgNUiagSj/CWZwRRbevJIg==
 
 zod@^3.9.5:
-  version "3.12.0"
-  resolved "https://registry.yarnpkg.com/zod/-/zod-3.12.0.tgz#84ba9f6bdb7835e2483982d5f52cfffcb6a00346"
-  integrity sha512-w+mmntgEL4hDDL5NLFdN6Fq2DSzxfmlSoJqiYE1/CApO8EkOCxvJvRYEVf8Vr/lRs3i6gqoiyFM6KRcWqqdBzQ==
+  version "3.13.4"
+  resolved "https://registry.yarnpkg.com/zod/-/zod-3.13.4.tgz#5d6fe03ef4824a637d7ef50b5441cf6ab3acede0"
+  integrity sha512-LZRucWt4j/ru5azOkJxCfpR87IyFDn8h2UODdqvXzZLb3K7bb9chUrUIGTy3BPsr8XnbQYfQ5Md5Hu2OYIo1mg==
 
 zwitch@^1.0.0:
   version "1.0.5"