diff --git a/patroni/dcs/kubernetes.py b/patroni/dcs/kubernetes.py
index c6ba3af9..6fcf4984 100644
--- a/patroni/dcs/kubernetes.py
+++ b/patroni/dcs/kubernetes.py
@@ -1215,9 +1215,6 @@ class Kubernetes(AbstractDCS):
 
         self._kinds.set(self.leader_path, kind)
 
-        if not retry.ensure_deadline(0.5):
-            return False
-
         kind_annotations = kind and kind.metadata.annotations or EMPTY_DICT
         kind_resource_version = kind and kind.metadata.resource_version
 
@@ -1225,6 +1222,14 @@ class Kubernetes(AbstractDCS):
         if kind and (kind_annotations.get(self._LEADER) != self._name or kind_resource_version == resource_version):
             return False
 
+        # We can get 409 because we do at least one retry, and the first update might have succeeded,
+        # therefore we will check if annotations on the read object match expectations.
+        if all(kind_annotations.get(k) == v for k, v in annotations.items()):
+            return True
+
+        if not retry.ensure_deadline(0.5):
+            return False
+
         return bool(_run_and_handle_exceptions(self._patch_or_create, self.leader_path, annotations,
                                                kind_resource_version, ips=ips, retry=_retry))
 
diff --git a/tests/test_kubernetes.py b/tests/test_kubernetes.py
index bf684ef4..dc4a1365 100644
--- a/tests/test_kubernetes.py
+++ b/tests/test_kubernetes.py
@@ -422,14 +422,18 @@ class TestKubernetesEndpoints(BaseTestKubernetes):
         self.assertFalse(self.k.update_leader(cluster, '123'))
         mock_patch.side_effect = RetryFailedError('')
         self.assertRaises(KubernetesError, self.k.update_leader, cluster, '123')
-        mock_patch.side_effect = k8s_client.rest.ApiException(409, '')
+        mock_patch.side_effect = [k8s_client.rest.ApiException(409, ''),
+                                  k8s_client.rest.ApiException(409, ''), mock_namespaced_kind()]
+        mock_read.return_value.metadata.resource_version = '2'
         with patch('time.time', Mock(side_effect=[0, 0, 100, 200, 0, 0, 0, 0, 0, 100, 200])):
             self.assertFalse(self.k.update_leader(cluster, '123'))
             self.assertFalse(self.k.update_leader(cluster, '123'))
+        mock_patch.side_effect = k8s_client.rest.ApiException(409, '')
         self.assertFalse(self.k.update_leader(cluster, '123'))
         mock_patch.side_effect = [k8s_client.rest.ApiException(409, ''), mock_namespaced_kind()]
-        mock_read.return_value.metadata.resource_version = '2'
-        self.assertIsNotNone(self.k._update_leader_with_retry({}, '1', []))
+        self.assertTrue(self.k._update_leader_with_retry({}, '1', []))
+        mock_patch.side_effect = [k8s_client.rest.ApiException(409, ''), mock_namespaced_kind()]
+        self.assertIsNotNone(self.k._update_leader_with_retry({'foo': 'bar'}, '1', []))
         mock_patch.side_effect = k8s_client.rest.ApiException(409, '')
         mock_read.side_effect = RetryFailedError('')
         self.assertRaises(KubernetesError, self.k.update_leader, cluster, '123')