diff --git a/apps/web/components/booking/AvailableTimes.tsx b/apps/web/components/booking/AvailableTimes.tsx
index 394225ba3a..a48b802d98 100644
--- a/apps/web/components/booking/AvailableTimes.tsx
+++ b/apps/web/components/booking/AvailableTimes.tsx
@@ -72,6 +72,7 @@ const AvailableTimes: FC<AvailableTimesProps> = ({
       slotUtcStartDate: slot.time,
       eventTypeId,
       slotUtcEndDate: dayjs(slot.time).utc().add(duration, "minutes").format(),
+      bookingAttendees: bookingAttendees || undefined,
     });
   };
 
diff --git a/apps/web/components/booking/pages/BookingPage.tsx b/apps/web/components/booking/pages/BookingPage.tsx
index 98a390f8a4..4b208c5951 100644
--- a/apps/web/components/booking/pages/BookingPage.tsx
+++ b/apps/web/components/booking/pages/BookingPage.tsx
@@ -230,12 +230,14 @@ const BookingPage = ({
     }),
     {}
   );
+
   const reserveSlot = () => {
     if (queryDuration) {
       reserveSlotMutation.mutate({
         eventTypeId: eventType.id,
         slotUtcStartDate: dayjs(queryDate).utc().format(),
         slotUtcEndDate: dayjs(queryDate).utc().add(parseInt(queryDuration), "minutes").format(),
+        bookingAttendees: currentSlotBooking ? currentSlotBooking.attendees.length : undefined,
       });
     }
   };
diff --git a/packages/features/bookings/lib/handleNewBooking.ts b/packages/features/bookings/lib/handleNewBooking.ts
index 338ecda022..9a69df44c7 100644
--- a/packages/features/bookings/lib/handleNewBooking.ts
+++ b/packages/features/bookings/lib/handleNewBooking.ts
@@ -1014,9 +1014,17 @@ async function handler(
           message?: string;
         })
       | null = null;
-    const booking = await prisma.booking.findUniqueOrThrow({
+    const booking = await prisma.booking.findFirst({
       where: {
-        uid: rescheduleUid || reqBody.bookingUid,
+        OR: [
+          {
+            uid: rescheduleUid || reqBody.bookingUid,
+          },
+          {
+            eventTypeId: eventType.id,
+            startTime: evt.startTime,
+          },
+        ],
       },
       select: {
         uid: true,
@@ -1029,6 +1037,11 @@ async function handler(
         status: true,
       },
     });
+
+    if (!booking) {
+      throw new HttpError({ statusCode: 404, message: "Could not find booking" });
+    }
+
     // See if attendee is already signed up for timeslot
     if (
       booking.attendees.find((attendee) => attendee.email === invitee[0].email) &&
diff --git a/packages/trpc/server/routers/viewer/slots/reserveSlot.handler.ts b/packages/trpc/server/routers/viewer/slots/reserveSlot.handler.ts
index 9f98448535..b258c78b46 100644
--- a/packages/trpc/server/routers/viewer/slots/reserveSlot.handler.ts
+++ b/packages/trpc/server/routers/viewer/slots/reserveSlot.handler.ts
@@ -21,41 +21,65 @@ interface ReserveSlotOptions {
 export const reserveSlotHandler = async ({ ctx, input }: ReserveSlotOptions) => {
   const { prisma, req, res } = ctx;
   const uid = req?.cookies?.uid || uuid();
-  const { slotUtcStartDate, slotUtcEndDate, eventTypeId } = input;
+  const { slotUtcStartDate, slotUtcEndDate, eventTypeId, bookingAttendees } = input;
   const releaseAt = dayjs.utc().add(parseInt(MINUTES_TO_BOOK), "minutes").format();
   const eventType = await prisma.eventType.findUnique({
     where: { id: eventTypeId },
     select: { users: { select: { id: true } }, seatsPerTimeSlot: true },
   });
-  if (eventType) {
-    await Promise.all(
-      eventType.users.map((user) =>
-        prisma.selectedSlots.upsert({
-          where: { selectedSlotUnique: { userId: user.id, slotUtcStartDate, slotUtcEndDate, uid } },
-          update: {
-            slotUtcStartDate,
-            slotUtcEndDate,
-            releaseAt,
-            eventTypeId,
-          },
-          create: {
-            userId: user.id,
-            eventTypeId,
-            slotUtcStartDate,
-            slotUtcEndDate,
-            uid,
-            releaseAt,
-            isSeat: eventType.seatsPerTimeSlot !== null,
-          },
-        })
-      )
-    );
-  } else {
+
+  if (!eventType) {
     throw new TRPCError({
       message: "Event type not found",
       code: "NOT_FOUND",
     });
   }
+
+  let shouldReserveSlot = true;
+
+  // If this is a seated event then don't reserve a slot
+  if (eventType.seatsPerTimeSlot) {
+    // Check to see if this is the last attendee
+    if (bookingAttendees) {
+      const seatsLeft = eventType.seatsPerTimeSlot - bookingAttendees;
+      if (seatsLeft < 1) shouldReserveSlot = false;
+    } else {
+      // If there is no booking yet then don't reserve the slot
+      shouldReserveSlot = false;
+    }
+  }
+
+  if (eventType && shouldReserveSlot) {
+    try {
+      await Promise.all(
+        eventType.users.map((user) =>
+          prisma.selectedSlots.upsert({
+            where: { selectedSlotUnique: { userId: user.id, slotUtcStartDate, slotUtcEndDate, uid } },
+            update: {
+              slotUtcStartDate,
+              slotUtcEndDate,
+              releaseAt,
+              eventTypeId,
+            },
+            create: {
+              userId: user.id,
+              eventTypeId,
+              slotUtcStartDate,
+              slotUtcEndDate,
+              uid,
+              releaseAt,
+              isSeat: eventType.seatsPerTimeSlot !== null,
+            },
+          })
+        )
+      );
+    } catch {
+      throw new TRPCError({
+        message: "Event type not found",
+        code: "NOT_FOUND",
+      });
+    }
+  }
   res?.setHeader("Set-Cookie", serialize("uid", uid, { path: "/", sameSite: "lax" }));
   return;
 };
diff --git a/packages/trpc/server/routers/viewer/slots/types.ts b/packages/trpc/server/routers/viewer/slots/types.ts
index f387f7059e..c980f558b2 100644
--- a/packages/trpc/server/routers/viewer/slots/types.ts
+++ b/packages/trpc/server/routers/viewer/slots/types.ts
@@ -33,6 +33,7 @@ export const reserveSlotSchema = z
     slotUtcStartDate: z.string(),
     // endTime ISOString
     slotUtcEndDate: z.string(),
+    bookingAttendees: z.number().optional(),
   })
   .refine(
     (data) => !!data.eventTypeId || !!data.slotUtcStartDate || !!data.slotUtcEndDate,