diff --git a/src/pretix/base/services/cart.py b/src/pretix/base/services/cart.py
index 936c4352a9..1479c9f1e1 100644
--- a/src/pretix/base/services/cart.py
+++ b/src/pretix/base/services/cart.py
@@ -233,7 +233,7 @@ class CartManager:
                 # TODO: i18n plurals
                 raise CartError(_(error_messages['max_items']) % (self.event.settings.max_items_per_order,))
 
-    def _check_item_constraints(self, op):
+    def _check_item_constraints(self, op, current_ops=[]):
         if isinstance(op, self.AddOperation) or isinstance(op, self.ExtendOperation):
             if not (
                 (isinstance(op, self.AddOperation) and op.addon_to == 'FAKE') or
@@ -305,10 +305,10 @@ class CartManager:
             if op.item.max_per_order or op.item.min_per_order:
                 new_total = (
                     len([1 for p in self.positions if p.item_id == op.item.pk]) +
-                    sum([_op.count for _op in self._operations
+                    sum([_op.count for _op in self._operations + current_ops
                          if isinstance(_op, self.AddOperation) and _op.item == op.item]) +
                     op.count -
-                    len([1 for _op in self._operations
+                    len([1 for _op in self._operations + current_ops
                          if isinstance(_op, self.RemoveOperation) and _op.position.item_id == op.item.pk])
                 )
 
@@ -571,7 +571,7 @@ class CartManager:
                     voucher=None, quotas=bundle_quotas, addon_to='FAKE', subevent=subevent,
                     includes_tax=bool(bprice.rate), bundled=[], seat=None
                 )
-                self._check_item_constraints(bop)
+                self._check_item_constraints(bop, operations)
                 bundled.append(bop)
 
             price = self._get_price(item, variation, voucher, i.get('price'), subevent, bundled_sum=bundled_sum)
@@ -580,7 +580,7 @@ class CartManager:
                 count=i['count'], item=item, variation=variation, price=price, voucher=voucher, quotas=quotas,
                 addon_to=False, subevent=subevent, includes_tax=bool(price.rate), bundled=bundled, seat=seat
             )
-            self._check_item_constraints(op)
+            self._check_item_constraints(op, operations)
             operations.append(op)
 
         self._quota_diff.update(quota_diff)
@@ -686,7 +686,7 @@ class CartManager:
                     count=1, item=item, variation=variation, price=price, voucher=None, quotas=quotas,
                     addon_to=cp, subevent=cp.subevent, includes_tax=bool(price.rate), bundled=[], seat=None
                 )
-                self._check_item_constraints(op)
+                self._check_item_constraints(op, operations)
                 operations.append(op)
 
         # Check constraints on the add-on combinations
diff --git a/src/tests/presale/test_cart.py b/src/tests/presale/test_cart.py
index e4c6b01704..051a487cc6 100644
--- a/src/tests/presale/test_cart.py
+++ b/src/tests/presale/test_cart.py
@@ -843,6 +843,20 @@ class CartTest(CartTestMixin, TestCase):
         with scopes_disabled():
             self.assertEqual(CartPosition.objects.filter(cart_id=self.session_key, event=self.event).count(), 1)
 
+    def test_max_per_item_variations_failed(self):
+        self.shirt.max_per_order = 1
+        self.shirt.save()
+        response = self.client.post('/%s/%s/cart/add' % (self.orga.slug, self.event.slug), {
+            'variation_%d_%d' % (self.shirt.id, self.shirt_blue.id): '1',
+            'variation_%d_%d' % (self.shirt.id, self.shirt_red.id): '1',
+        }, follow=True)
+        self.assertRedirects(response, '/%s/%s/?require_cookie=true' % (self.orga.slug, self.event.slug),
+                             target_status_code=200)
+        doc = BeautifulSoup(response.rendered_content, "lxml")
+        self.assertIn('more than', doc.select('.alert-danger')[0].text)
+        with scopes_disabled():
+            self.assertEqual(CartPosition.objects.filter(cart_id=self.session_key, event=self.event).count(), 0)
+
     def test_max_per_item_failed(self):
         self.ticket.max_per_order = 2
         self.ticket.save()