diff --git a/src/pretix/base/services/orders.py b/src/pretix/base/services/orders.py
index 863ca76cd2..e8be424cf5 100644
--- a/src/pretix/base/services/orders.py
+++ b/src/pretix/base/services/orders.py
@@ -146,6 +146,10 @@ error_messages = {
     'race_condition': gettext_lazy("This order was changed by someone else simultaneously. Please check if your "
                                    "changes are still accurate and try again."),
     'empty': gettext_lazy("Your cart is empty."),
+    'max_items': ngettext_lazy(
+        "You cannot select more than %s item per order.",
+        "You cannot select more than %s items per order."
+    ),
     'max_items_per_product': ngettext_lazy(
         "You cannot select more than %(max)s item of the product %(product)s. We removed the surplus items from your cart.",
         "You cannot select more than %(max)s items of the product %(product)s. We removed the surplus items from your cart.",
@@ -763,6 +767,11 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
                 shared_lock_objects=[event]
             )
 
+    # Check maximum order size
+    limit = min(int(event.settings.max_items_per_order), settings.PRETIX_MAX_ORDER_SIZE)
+    if sum(1 for cp in sorted_positions if not cp.addon_to) > limit:
+        err = err or (error_messages['max_items'] % limit)
+
     # Check availability
     for i, cp in enumerate(sorted_positions):
         if cp.pk in deleted_positions:
diff --git a/src/tests/presale/test_checkout.py b/src/tests/presale/test_checkout.py
index d2e66a9ef5..17d43e9d91 100644
--- a/src/tests/presale/test_checkout.py
+++ b/src/tests/presale/test_checkout.py
@@ -3625,6 +3625,47 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
             self.assertEqual(Order.objects.count(), 1)
             self.assertEqual(OrderPosition.objects.count(), 1)
 
+    def test_max_items_per_order_failed(self):
+        self.event.settings.max_items_per_order = 2
+        self.ticket.save()
+        with scopes_disabled():
+            ItemAddOn.objects.create(base_item=self.ticket, addon_category=self.workshopcat)
+            cp = CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.ticket,
+                price=23, expires=now() + timedelta(minutes=10),
+            )
+            CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.workshop1, addon_to=cp,
+                price=12, expires=now() + timedelta(minutes=10),
+            )
+            CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.ticket,
+                price=23, expires=now() + timedelta(minutes=10),
+            )
+            to_delete = CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.ticket,
+                price=23, expires=now() + timedelta(minutes=10),
+            )
+        self._set_payment()
+
+        response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
+        doc = BeautifulSoup(response.content.decode(), "lxml")
+        with scopes_disabled():
+            self.assertEqual(CartPosition.objects.filter(cart_id=self.session_key).count(), 4)
+            self.assertEqual(len(doc.select(".alert-danger")), 1)
+            self.assertFalse(Order.objects.exists())
+
+        with scopes_disabled():
+            to_delete.delete()
+        self.client.get('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug))  # required for session['shown_total']
+
+        response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
+        doc = BeautifulSoup(response.content.decode(), "lxml")
+        with scopes_disabled():
+            self.assertEqual(len(doc.select(".thank-you")), 1)
+            self.assertEqual(Order.objects.count(), 1)
+            self.assertEqual(OrderPosition.objects.count(), 3)
+
     def test_subevent_confirm_expired_partial(self):
         self.event.has_subevents = True
         self.event.save()