diff --git a/pkg/controller/deployment/deployment_controller.go b/pkg/controller/deployment/deployment_controller.go
index 304164ad94b..ea3d9e12cbd 100644
--- a/pkg/controller/deployment/deployment_controller.go
+++ b/pkg/controller/deployment/deployment_controller.go
@@ -581,6 +581,20 @@ func (dc *DeploymentController) syncDeployment(key string) error {
 		return nil
 	}
 
+	// This is the point at which we used to add/remove the overlap annotation.
+	// Now we always remove it if it exists, because it is obsolete as of 1.6.
+	// Although the server no longer adds or looks at the annotation,
+	// it's important to remove it from controllers created before the upgrade,
+	// so that old clients (e.g. kubectl reaper) know they can no longer assume
+	// the controller is blocked due to selector overlap and has no dependents.
+	if _, ok := d.Annotations[util.OverlapAnnotation]; ok {
+		delete(d.Annotations, util.OverlapAnnotation)
+		d, err = dc.client.ExtensionsV1beta1().Deployments(d.Namespace).UpdateStatus(d)
+		if err != nil {
+			return fmt.Errorf("couldn't remove obsolete overlap annotation from deployment %v: %v", key, err)
+		}
+	}
+
 	// List ReplicaSets owned by this Deployment, while reconciling ControllerRef
 	// through adoption/orphaning.
 	rsList, err := dc.getReplicaSetsForDeployment(d)
diff --git a/pkg/controller/deployment/deployment_controller_test.go b/pkg/controller/deployment/deployment_controller_test.go
index 7e2638b8563..802b33df2fb 100644
--- a/pkg/controller/deployment/deployment_controller_test.go
+++ b/pkg/controller/deployment/deployment_controller_test.go
@@ -254,6 +254,32 @@ func TestSyncDeploymentCreatesReplicaSet(t *testing.T) {
 	f.run(getKey(d, t))
 }
 
+func TestSyncDeploymentClearsOverlapAnnotation(t *testing.T) {
+	f := newFixture(t)
+
+	d := newDeployment("foo", 1, nil, nil, nil, map[string]string{"foo": "bar"})
+	d.Annotations[util.OverlapAnnotation] = "overlap"
+	f.dLister = append(f.dLister, d)
+	f.objects = append(f.objects, d)
+
+	rs := newReplicaSet(d, "deploymentrs-4186632231", 1)
+
+	f.expectUpdateDeploymentStatusAction(d)
+	f.expectCreateRSAction(rs)
+	f.expectUpdateDeploymentStatusAction(d)
+	f.expectUpdateDeploymentStatusAction(d)
+
+	f.run(getKey(d, t))
+
+	d, err := f.client.ExtensionsV1beta1().Deployments(d.Namespace).Get(d.Name, metav1.GetOptions{})
+	if err != nil {
+		t.Fatalf("can't get deployment: %v", err)
+	}
+	if _, ok := d.Annotations[util.OverlapAnnotation]; ok {
+		t.Errorf("OverlapAnnotation = %q, wanted absent", d.Annotations[util.OverlapAnnotation])
+	}
+}
+
 func TestSyncDeploymentDontDoAnythingDuringDeletion(t *testing.T) {
 	f := newFixture(t)