diff --git a/netbox/extras/querysets.py b/netbox/extras/querysets.py
index 478dedf92d6..c1de291ed24 100644
--- a/netbox/extras/querysets.py
+++ b/netbox/extras/querysets.py
@@ -120,17 +120,14 @@ def _get_config_context_filters(self):
         if self.model._meta.model_name == 'device':
             base_query.add((Q(locations=OuterRef('location')) | Q(locations=None)), Q.AND)
             base_query.add((Q(device_types=OuterRef('device_type')) | Q(device_types=None)), Q.AND)
-            base_query.add((Q(roles=OuterRef('role')) | Q(roles=None)), Q.AND)
-            base_query.add((Q(sites=OuterRef('site')) | Q(sites=None)), Q.AND)
-            region_field = 'site__region'
-            sitegroup_field = 'site__group'
 
         elif self.model._meta.model_name == 'virtualmachine':
-            base_query.add((Q(roles=OuterRef('role')) | Q(roles=None)), Q.AND)
-            base_query.add((Q(sites=OuterRef('cluster__site')) | Q(sites=None)), Q.AND)
             base_query.add(Q(device_types=None), Q.AND)
-            region_field = 'cluster__site__region'
-            sitegroup_field = 'cluster__site__group'
+
+        base_query.add((Q(roles=OuterRef('role')) | Q(roles=None)), Q.AND)
+        base_query.add((Q(sites=OuterRef('site')) | Q(sites=None)), Q.AND)
+        region_field = 'site__region'
+        sitegroup_field = 'site__group'
 
         base_query.add(
             (Q(
diff --git a/netbox/extras/tests/test_models.py b/netbox/extras/tests/test_models.py
index ef939840119..26c951601c7 100644
--- a/netbox/extras/tests/test_models.py
+++ b/netbox/extras/tests/test_models.py
@@ -270,7 +270,12 @@ def test_annotation_same_as_get_for_object_virtualmachine_relations(self):
         tag = Tag.objects.first()
         cluster_type = ClusterType.objects.create(name="Cluster Type")
         cluster_group = ClusterGroup.objects.create(name="Cluster Group")
-        cluster = Cluster.objects.create(name="Cluster", group=cluster_group, type=cluster_type)
+        cluster = Cluster.objects.create(
+            name="Cluster",
+            group=cluster_group,
+            type=cluster_type,
+            site=site,
+        )
 
         region_context = ConfigContext.objects.create(
             name="region",
@@ -354,6 +359,106 @@ def test_annotation_same_as_get_for_object_virtualmachine_relations(self):
         annotated_queryset = VirtualMachine.objects.filter(name=virtual_machine.name).annotate_config_context_data()
         self.assertEqual(virtual_machine.get_config_context(), annotated_queryset[0].get_config_context())
 
+    def test_annotation_same_as_get_for_object_virtualmachine_relations_direct_site(self):
+        region = Region.objects.first()
+        sitegroup = SiteGroup.objects.first()
+        site = Site.objects.first()
+        platform = Platform.objects.first()
+        tenantgroup = TenantGroup.objects.first()
+        tenant = Tenant.objects.first()
+        tag = Tag.objects.first()
+        cluster_type = ClusterType.objects.create(name="Cluster Type")
+        cluster_group = ClusterGroup.objects.create(name="Cluster Group")
+        cluster = Cluster.objects.create(
+            name="Cluster",
+            group=cluster_group,
+            type=cluster_type,
+            site=site,
+        )
+
+        region_context = ConfigContext.objects.create(
+            name="region",
+            weight=100,
+            data={"region": 1}
+        )
+        region_context.regions.add(region)
+
+        sitegroup_context = ConfigContext.objects.create(
+            name="sitegroup",
+            weight=100,
+            data={"sitegroup": 1}
+        )
+        sitegroup_context.site_groups.add(sitegroup)
+
+        site_context = ConfigContext.objects.create(
+            name="site",
+            weight=100,
+            data={"site": 1}
+        )
+        site_context.sites.add(site)
+
+        platform_context = ConfigContext.objects.create(
+            name="platform",
+            weight=100,
+            data={"platform": 1}
+        )
+        platform_context.platforms.add(platform)
+
+        tenant_group_context = ConfigContext.objects.create(
+            name="tenant group",
+            weight=100,
+            data={"tenant_group": 1}
+        )
+        tenant_group_context.tenant_groups.add(tenantgroup)
+
+        tenant_context = ConfigContext.objects.create(
+            name="tenant",
+            weight=100,
+            data={"tenant": 1}
+        )
+        tenant_context.tenants.add(tenant)
+
+        tag_context = ConfigContext.objects.create(
+            name="tag",
+            weight=100,
+            data={"tag": 1}
+        )
+        tag_context.tags.add(tag)
+
+        cluster_type_context = ConfigContext.objects.create(
+            name="cluster type",
+            weight=100,
+            data={"cluster_type": 1}
+        )
+        cluster_type_context.cluster_types.add(cluster_type)
+
+        cluster_group_context = ConfigContext.objects.create(
+            name="cluster group",
+            weight=100,
+            data={"cluster_group": 1}
+        )
+        cluster_group_context.cluster_groups.add(cluster_group)
+
+        cluster_context = ConfigContext.objects.create(
+            name="cluster",
+            weight=100,
+            data={"cluster": 1}
+        )
+        cluster_context.clusters.add(cluster)
+
+        virtual_machine = VirtualMachine.objects.create(
+            name="VM 2",
+            site=site,
+            tenant=tenant,
+            platform=platform,
+            role=DeviceRole.objects.first()
+        )
+        virtual_machine.tags.add(tag)
+
+        annotated_queryset = VirtualMachine.objects.filter(name=virtual_machine.name).annotate_config_context_data()
+
+        self.assertEqual(virtual_machine.get_config_context(), annotated_queryset[0].get_config_context())
+
     def test_multiple_tags_return_distinct_objects(self):
         """
         Tagged items use a generic relationship, which results in duplicate rows being returned when queried.