diff --git a/server/src/business-layer/services/StripeService.ts b/server/src/business-layer/services/StripeService.ts
index 9e508ac39..af8d621f2 100644
--- a/server/src/business-layer/services/StripeService.ts
+++ b/server/src/business-layer/services/StripeService.ts
@@ -20,6 +20,7 @@ import {
 import BookingSlotService from "data-layer/services/BookingSlotsService"
 import console from "console"
 import MailService from "./MailService"
+import BookingUtils from "../utils/BookingUtils"
 
 const stripe = new Stripe(process.env.STRIPE_API_KEY)
 
@@ -432,6 +433,12 @@ export default class StripeService {
           stripe_payment_id: session.id,
           user_id: uid
         })
+
+        // Check if the last spot is taken and expire other sessions
+        const isLastSpot = await BookingUtils.isLastSpotTaken(bookingSlotId)
+        if (isLastSpot) {
+          await this.expireOtherCheckoutSessions(bookingSlotId)
+        }
       })
     )
     /**
@@ -452,6 +459,40 @@ export default class StripeService {
     }
   }
 
+  private async expireOtherCheckoutSessions(
+    bookingSlotId: string
+  ): Promise<void> {
+    try {
+      // Fetch all checkout sessions for the specific booking slot id
+      const sessions = await this.getRecentActiveSessions(
+        CheckoutTypeValues.BOOKING,
+        1440
+      )
+
+      const sessionsToExpire = sessions.filter((session) => {
+        const bookingSlots = JSON.parse(
+          session.metadata[BOOKING_SLOTS_KEY]
+        ) as Array<string>
+        return bookingSlots.includes(bookingSlotId)
+      })
+
+      // Expire each session that matches the booking slot id
+      await Promise.all(
+        sessionsToExpire.map(async (session) => {
+          if (session.id) {
+            await stripe.checkout.sessions.expire(session.id)
+          }
+        })
+      )
+
+      console.log(
+        `[WEBHOOK] Expired ${sessionsToExpire.length} sessions for booking slot ${bookingSlotId}`
+      )
+    } catch (err) {
+      console.error(`[WEBHOOK] Error expiring checkout sessions: ${err}`)
+    }
+  }
+
   public async addCouponToUser(
     stripeId: string,
     amount: number
diff --git a/server/src/business-layer/utils/BookingUtils.test.ts b/server/src/business-layer/utils/BookingUtils.test.ts
index 8d5657a7c..d63b2b301 100644
--- a/server/src/business-layer/utils/BookingUtils.test.ts
+++ b/server/src/business-layer/utils/BookingUtils.test.ts
@@ -1,6 +1,10 @@
 import { Timestamp } from "firebase-admin/firestore"
 import BookingUtils, { _earliestDate, _latestDate } from "./BookingUtils"
 import { LodgePricingTypeValues } from "./StripeProductMetadata"
+import BookingDataService from "../../data-layer/services/BookingDataService"
+import { cleanFirestore } from "../../test-config/TestUtils"
+import { BookingSlot } from "../../data-layer/models/firebase"
+import BookingSlotsService from "../../data-layer/services/BookingSlotsService"
 
 describe("BookingUtils", () => {
   describe("hasInvalidStartAndEndDates", () => {
@@ -95,4 +99,64 @@ describe("BookingUtils", () => {
       )
     })
   })
+
+  describe("isLastSpotTaken", () => {
+    afterEach(async () => {
+      await cleanFirestore()
+    })
+
+    it("should return true if the last spot is taken", async () => {
+      // Create a booking slot with a maximum of 2 bookings
+      const timestamp = Timestamp.fromDate(new Date(2024, 4, 23))
+      const bookingSlotData: BookingSlot = {
+        date: timestamp,
+        description: "booking_slot_description",
+        max_bookings: 2
+      }
+      const { id: slotId } = await new BookingSlotsService().createBookingSlot(
+        bookingSlotData
+      )
+
+      // Create two bookings for the same slot
+      await new BookingDataService().createBooking({
+        user_id: "ronaldo",
+        booking_slot_id: slotId,
+        stripe_payment_id: "stripeID3"
+      })
+
+      await new BookingDataService().createBooking({
+        user_id: "sui",
+        booking_slot_id: slotId,
+        stripe_payment_id: "stripeID1"
+      })
+
+      const result = await BookingUtils.isLastSpotTaken(slotId)
+
+      expect(result).toBe(true)
+    })
+
+    it("should return false if spots are still available", async () => {
+      // Create a booking slot with a maximum of 7 bookings
+      const timestamp = Timestamp.fromDate(new Date(2024, 4, 23))
+      const bookingSlotData: BookingSlot = {
+        date: timestamp,
+        description: "booking_slot_description",
+        max_bookings: 7
+      }
+      const { id: slotId } = await new BookingSlotsService().createBookingSlot(
+        bookingSlotData
+      )
+
+      // Create 1 booking for the slot
+      await new BookingDataService().createBooking({
+        user_id: "sdf",
+        booking_slot_id: slotId,
+        stripe_payment_id: "stripeID3"
+      })
+
+      const result = await BookingUtils.isLastSpotTaken(slotId)
+
+      expect(result).toBe(false)
+    })
+  })
 })
diff --git a/server/src/business-layer/utils/BookingUtils.ts b/server/src/business-layer/utils/BookingUtils.ts
index bff66c29f..8f6a02ca9 100644
--- a/server/src/business-layer/utils/BookingUtils.ts
+++ b/server/src/business-layer/utils/BookingUtils.ts
@@ -1,6 +1,8 @@
 import { Timestamp } from "firebase-admin/firestore"
 import { LodgePricingTypeValues } from "./StripeProductMetadata"
 import { firestoreTimestampToDate } from "data-layer/adapters/DateUtils"
+import BookingDataService from "../../data-layer/services/BookingDataService"
+import BookingSlotService from "../../data-layer/services/BookingSlotsService"
 
 // Need to validate the booking date through a startDate and endDate range.
 /**
@@ -90,6 +92,25 @@ const BookingUtils = {
     } else {
       return LodgePricingTypeValues.Normal
     }
+  },
+
+  /**
+   * Checks if the last spot is taken for a specific booking slot
+   * @param bookingSlotId The ID of the booking slot
+   * @returns true if the last spot is taken, false otherwise
+   */
+  isLastSpotTaken: async function (bookingSlotId: string): Promise<boolean> {
+    const bookingDataService = new BookingDataService()
+    const bookingSlotService = new BookingSlotService()
+
+    const bookingSlot =
+      await bookingSlotService.getBookingSlotById(bookingSlotId)
+
+    const bookings = await bookingDataService.getBookingsBySlotId(bookingSlotId)
+    const bookingCount = bookings.length
+
+    const availableSlots = bookingSlot.max_bookings - bookingCount
+    return availableSlots <= 0
   }
 } as const