diff --git a/pkg/controller/framework/controller.go b/pkg/controller/framework/controller.go
index bb839b3cd98..ca182343aa4 100644
--- a/pkg/controller/framework/controller.go
+++ b/pkg/controller/framework/controller.go
@@ -106,6 +106,16 @@ func (c *Controller) HasSynced() bool {
 	return c.reflector.LastSyncResourceVersion() != ""
 }
 
+// Requeue adds the provided object back into the queue if it does not already exist.
+func (c *Controller) Requeue(obj interface{}) error {
+	return c.config.Queue.AddIfNotPresent(cache.Deltas{
+		cache.Delta{
+			Type:   cache.Sync,
+			Object: obj,
+		},
+	})
+}
+
 // processLoop drains the work queue.
 // TODO: Consider doing the processing in parallel. This will require a little thought
 // to make sure that we don't end up processing the same object multiple times
diff --git a/pkg/controller/namespace/namespace_controller.go b/pkg/controller/namespace/namespace_controller.go
index 40f33e1c183..17963877aae 100644
--- a/pkg/controller/namespace/namespace_controller.go
+++ b/pkg/controller/namespace/namespace_controller.go
@@ -17,6 +17,7 @@ limitations under the License.
 package namespacecontroller
 
 import (
+	"fmt"
 	"time"
 
 	"k8s.io/kubernetes/pkg/api"
@@ -41,7 +42,8 @@ type NamespaceController struct {
 
 // NewNamespaceController creates a new NamespaceController
 func NewNamespaceController(kubeClient client.Interface, resyncPeriod time.Duration) *NamespaceController {
-	_, controller := framework.NewInformer(
+	var controller *framework.Controller
+	_, controller = framework.NewInformer(
 		&cache.ListWatch{
 			ListFunc: func() (runtime.Object, error) {
 				return kubeClient.Namespaces().List(labels.Everything(), fields.Everything())
@@ -55,16 +57,41 @@ func NewNamespaceController(kubeClient client.Interface, resyncPeriod time.Durat
 		framework.ResourceEventHandlerFuncs{
 			AddFunc: func(obj interface{}) {
 				namespace := obj.(*api.Namespace)
-				err := syncNamespace(kubeClient, *namespace)
-				if err != nil {
-					glog.Error(err)
+				if err := syncNamespace(kubeClient, *namespace); err != nil {
+					if estimate, ok := err.(*contentRemainingError); ok {
+						go func() {
+							// Estimate is the aggregate total of TerminationGracePeriodSeconds, which defaults to 30s
+							// for pods.  However, most processes will terminate faster - within a few seconds, probably
+							// with a peak within 5-10s.  So this division is a heuristic that avoids waiting the full
+							// duration when in many cases things complete more quickly. The extra second added is to
+							// ensure we never wait 0 seconds.
+							t := estimate.Estimate/2 + 1
+							glog.V(4).Infof("Content remaining in namespace %s, waiting %d seconds", namespace.Name, t)
+							time.Sleep(time.Duration(t) * time.Second)
+							if err := controller.Requeue(namespace); err != nil {
+								util.HandleError(err)
+							}
+						}()
+						return
+					}
+					util.HandleError(err)
 				}
 			},
 			UpdateFunc: func(oldObj, newObj interface{}) {
 				namespace := newObj.(*api.Namespace)
-				err := syncNamespace(kubeClient, *namespace)
-				if err != nil {
-					glog.Error(err)
+				if err := syncNamespace(kubeClient, *namespace); err != nil {
+					if estimate, ok := err.(*contentRemainingError); ok {
+						go func() {
+							t := estimate.Estimate/2 + 1
+							glog.V(4).Infof("Content remaining in namespace %s, waiting %d seconds", namespace.Name, t)
+							time.Sleep(time.Duration(t) * time.Second)
+							if err := controller.Requeue(namespace); err != nil {
+								util.HandleError(err)
+							}
+						}()
+						return
+					}
+					util.HandleError(err)
 				}
 			},
 		},
@@ -114,45 +141,56 @@ func finalize(kubeClient client.Interface, namespace api.Namespace) (*api.Namesp
 	return kubeClient.Namespaces().Finalize(&namespaceFinalize)
 }
 
-// deleteAllContent will delete all content known to the system in a namespace
-func deleteAllContent(kubeClient client.Interface, namespace string) (err error) {
+type contentRemainingError struct {
+	Estimate int64
+}
+
+func (e *contentRemainingError) Error() string {
+	return fmt.Sprintf("some content remains in the namespace, estimate %d seconds before it is removed", e.Estimate)
+}
+
+// deleteAllContent will delete all content known to the system in a namespace. It returns an estimate
+// of the time remaining before the remaining resources are deleted. If estimate > 0 not all resources
+// are guaranteed to be gone.
+func deleteAllContent(kubeClient client.Interface, namespace string, before util.Time) (estimate int64, err error) {
 	err = deleteServiceAccounts(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteServices(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteReplicationControllers(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
-	err = deletePods(kubeClient, namespace)
+	estimate, err = deletePods(kubeClient, namespace, before)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteSecrets(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deletePersistentVolumeClaims(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteLimitRanges(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteResourceQuotas(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
 	err = deleteEvents(kubeClient, namespace)
 	if err != nil {
-		return err
+		return estimate, err
 	}
-	return nil
+
+	return estimate, nil
 }
 
 // syncNamespace makes namespace life-cycle decisions
@@ -160,6 +198,7 @@ func syncNamespace(kubeClient client.Interface, namespace api.Namespace) (err er
 	if namespace.DeletionTimestamp == nil {
 		return nil
 	}
+	glog.V(4).Infof("Syncing namespace %s", namespace.Name)
 
 	// if there is a deletion timestamp, and the status is not terminating, then update status
 	if !namespace.DeletionTimestamp.IsZero() && namespace.Status.Phase != api.NamespaceTerminating {
@@ -185,10 +224,13 @@ func syncNamespace(kubeClient client.Interface, namespace api.Namespace) (err er
 	}
 
 	// there may still be content for us to remove
-	err = deleteAllContent(kubeClient, namespace.Name)
+	estimate, err := deleteAllContent(kubeClient, namespace.Name, *namespace.DeletionTimestamp)
 	if err != nil {
 		return err
 	}
+	if estimate > 0 {
+		return &contentRemainingError{estimate}
+	}
 
 	// we have removed content, so mark it finalized by us
 	result, err := finalize(kubeClient, namespace)
@@ -277,18 +319,33 @@ func deleteReplicationControllers(kubeClient client.Interface, ns string) error
 	return nil
 }
 
-func deletePods(kubeClient client.Interface, ns string) error {
+func deletePods(kubeClient client.Interface, ns string, before util.Time) (int64, error) {
 	items, err := kubeClient.Pods(ns).List(labels.Everything(), fields.Everything())
 	if err != nil {
-		return err
+		return 0, err
 	}
+	expired := util.Now().After(before.Time)
+	var deleteOptions *api.DeleteOptions
+	if expired {
+		deleteOptions = api.NewDeleteOptions(0)
+	}
+	estimate := int64(0)
 	for i := range items.Items {
-		err := kubeClient.Pods(ns).Delete(items.Items[i].Name, nil)
+		if items.Items[i].Spec.TerminationGracePeriodSeconds != nil {
+			grace := *items.Items[i].Spec.TerminationGracePeriodSeconds
+			if grace > estimate {
+				estimate = grace
+			}
+		}
+		err := kubeClient.Pods(ns).Delete(items.Items[i].Name, deleteOptions)
 		if err != nil && !errors.IsNotFound(err) {
-			return err
+			return 0, err
 		}
 	}
-	return nil
+	if expired {
+		estimate = 0
+	}
+	return estimate, nil
 }
 
 func deleteEvents(kubeClient client.Interface, ns string) error {