diff --git a/pkg/operator/workload_controller_openshiftapiserver_v311_00.go b/pkg/operator/workload_controller_openshiftapiserver_v311_00.go
index b1a2495ce..23a452f24 100644
--- a/pkg/operator/workload_controller_openshiftapiserver_v311_00.go
+++ b/pkg/operator/workload_controller_openshiftapiserver_v311_00.go
@@ -103,7 +103,9 @@ func syncOpenShiftAPIServer_v311_00_to_latest(c OpenShiftAPIServerOperator, orig
 		})
 	}
 
-	if actualDaemonSet.ObjectMeta.Generation == operatorConfig.Status.ObservedGeneration {
+	// If the daemonset is up to date and the operatorConfig are up to date, then we are no longer progressing
+	if actualDaemonSet.ObjectMeta.Generation == actualDaemonSet.Status.ObservedGeneration &&
+		operatorConfig.ObjectMeta.Generation == operatorConfig.Status.ObservedGeneration {
 		v1helpers.SetOperatorCondition(&operatorConfig.Status.Conditions, operatorv1.OperatorCondition{
 			Type:   operatorv1.OperatorStatusTypeProgressing,
 			Status: operatorv1.ConditionFalse,