diff --git a/pkg/controller/deployment/sync.go b/pkg/controller/deployment/sync.go
index d2aa4d2b18c..a5b606be2c0 100644
--- a/pkg/controller/deployment/sync.go
+++ b/pkg/controller/deployment/sync.go
@@ -547,6 +547,7 @@ func (dc *DeploymentController) cleanupDeployment(oldRSs []*extensions.ReplicaSe
 	}
 
 	sort.Sort(controller.ReplicaSetsByCreationTimestamp(oldRSs))
+	glog.V(2).Infof("Looking to cleanup old replica sets for deployment %q", deployment.Name)
 
 	var errList []error
 	// TODO: This should be parallelized.
@@ -556,6 +557,7 @@ func (dc *DeploymentController) cleanupDeployment(oldRSs []*extensions.ReplicaSe
 		if rs.Status.Replicas != 0 || *(rs.Spec.Replicas) != 0 || rs.Generation > rs.Status.ObservedGeneration {
 			continue
 		}
+		glog.V(2).Infof("Trying to cleanup replica set %q for deployment %q", rs.Name, deployment.Name)
 		if err := dc.client.Extensions().ReplicaSets(rs.Namespace).Delete(rs.Name, nil); err != nil && !errors.IsNotFound(err) {
 			glog.V(2).Infof("Failed deleting old replica set %v for deployment %v: %v", rs.Name, deployment.Name, err)
 			errList = append(errList, err)
diff --git a/test/e2e/framework/util.go b/test/e2e/framework/util.go
index 98bd12e8d5f..8986ac2c601 100644
--- a/test/e2e/framework/util.go
+++ b/test/e2e/framework/util.go
@@ -3422,17 +3422,27 @@ func WaitForPodsReady(c clientset.Interface, ns, name string, minReadySeconds in
 
 // Waits for the deployment to clean up old rcs.
 func WaitForDeploymentOldRSsNum(c clientset.Interface, ns, deploymentName string, desiredRSNum int) error {
-	return wait.Poll(Poll, 5*time.Minute, func() (bool, error) {
+	var oldRSs []*extensions.ReplicaSet
+	var d *extensions.Deployment
+
+	pollErr := wait.PollImmediate(Poll, 5*time.Minute, func() (bool, error) {
 		deployment, err := c.Extensions().Deployments(ns).Get(deploymentName, metav1.GetOptions{})
 		if err != nil {
 			return false, err
 		}
-		_, oldRSs, err := deploymentutil.GetOldReplicaSets(deployment, c)
+		d = deployment
+
+		_, oldRSs, err = deploymentutil.GetOldReplicaSets(deployment, c)
 		if err != nil {
 			return false, err
 		}
 		return len(oldRSs) == desiredRSNum, nil
 	})
+	if pollErr == wait.ErrWaitTimeout {
+		pollErr = fmt.Errorf("%d old replica sets were not cleaned up for deployment %q", len(oldRSs)-desiredRSNum, deploymentName)
+		logReplicaSetsOfDeployment(d, oldRSs, nil)
+	}
+	return pollErr
 }
 
 func logReplicaSetsOfDeployment(deployment *extensions.Deployment, allOldRSs []*extensions.ReplicaSet, newRS *extensions.ReplicaSet) {