diff --git a/cmd/kube-controller-manager/app/controllermanager.go b/cmd/kube-controller-manager/app/controllermanager.go
index dc6e2953954..2d3849d6a44 100644
--- a/cmd/kube-controller-manager/app/controllermanager.go
+++ b/cmd/kube-controller-manager/app/controllermanager.go
@@ -144,7 +144,7 @@ func (s *CMServer) Run(_ []string) error {
 	go util.Forever(func() { endpoints.SyncServiceEndpoints() }, time.Second*10)
 
 	controllerManager := replicationControllerPkg.NewReplicationManager(kubeClient)
-	controllerManager.Run(10 * time.Second)
+	controllerManager.Run(replicationControllerPkg.DefaultSyncPeriod)
 
 	kubeletClient, err := client.NewKubeletClient(&s.KubeletConfig)
 	if err != nil {
diff --git a/cmd/kubernetes/kubernetes.go b/cmd/kubernetes/kubernetes.go
index 307abbb85cf..66446920041 100644
--- a/cmd/kubernetes/kubernetes.go
+++ b/cmd/kubernetes/kubernetes.go
@@ -133,7 +133,7 @@ func runControllerManager(machineList []string, cl *client.Client, nodeMilliCPU,
 	go util.Forever(func() { endpoints.SyncServiceEndpoints() }, time.Second*10)
 
 	controllerManager := controller.NewReplicationManager(cl)
-	controllerManager.Run(10 * time.Second)
+	controllerManager.Run(controller.DefaultSyncPeriod)
 }
 
 func startComponents(etcdClient tools.EtcdClient, cl *client.Client, addr net.IP, port int) {
diff --git a/pkg/controller/replication_controller.go b/pkg/controller/replication_controller.go
index ba9353c585f..190292e2abe 100644
--- a/pkg/controller/replication_controller.go
+++ b/pkg/controller/replication_controller.go
@@ -56,6 +56,9 @@ type RealPodControl struct {
 	kubeClient client.Interface
 }
 
+// Time period of main replication controller sync loop
+const DefaultSyncPeriod = 10 * time.Second
+
 func (r RealPodControl) createReplica(namespace string, controller api.ReplicationController) {
 	desiredLabels := make(labels.Set)
 	for k, v := range controller.Spec.Template.Labels {
diff --git a/pkg/kubectl/cmd/resize.go b/pkg/kubectl/cmd/resize.go
index c55b07b6751..91905c50e47 100644
--- a/pkg/kubectl/cmd/resize.go
+++ b/pkg/kubectl/cmd/resize.go
@@ -19,9 +19,12 @@ package cmd
 import (
 	"fmt"
 	"io"
+	"time"
 
+	"github.com/GoogleCloudPlatform/kubernetes/pkg/controller"
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/kubectl"
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/kubectl/cmd/util"
+	"github.com/GoogleCloudPlatform/kubernetes/pkg/util/wait"
 	"github.com/spf13/cobra"
 )
 
@@ -37,6 +40,9 @@ $ kubectl resize --replicas=3 replicationcontrollers foo
 
 // If the replication controller named foo's current size is 2, resize foo to 3.
 $ kubectl resize --current-replicas=2 --replicas=3 replicationcontrollers foo`
+
+	retryFrequency = controller.DefaultSyncPeriod / 100
+	retryTimeout   = 10 * time.Second
 )
 
 func (f *Factory) NewCmdResize(out io.Writer) *cobra.Command {
@@ -63,9 +69,15 @@ func (f *Factory) NewCmdResize(out io.Writer) *cobra.Command {
 
 			resourceVersion := util.GetFlagString(cmd, "resource-version")
 			currentSize := util.GetFlagInt(cmd, "current-replicas")
-			s, err := resizer.Resize(namespace, name, &kubectl.ResizePrecondition{currentSize, resourceVersion}, uint(count))
-			checkErr(err)
-			fmt.Fprintf(out, "%s\n", s)
+			precondition := &kubectl.ResizePrecondition{currentSize, resourceVersion}
+			cond := kubectl.ResizeCondition(resizer, precondition, namespace, name, uint(count))
+
+			msg := "resized"
+			if err = wait.Poll(retryFrequency, retryTimeout, cond); err != nil {
+				msg = fmt.Sprintf("Failed to resize controller in spite of retrying for %s", retryTimeout)
+				checkErr(err)
+			}
+			fmt.Fprintf(out, "%s\n", msg)
 		},
 	}
 	cmd.Flags().String("resource-version", "", "Precondition for resource version. Requires that the current resource version match this value in order to resize.")
diff --git a/pkg/kubectl/resize.go b/pkg/kubectl/resize.go
index ff3f866a631..b10ebe9f663 100644
--- a/pkg/kubectl/resize.go
+++ b/pkg/kubectl/resize.go
@@ -22,6 +22,7 @@ import (
 
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/api"
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/client"
+	"github.com/GoogleCloudPlatform/kubernetes/pkg/util/wait"
 )
 
 // ResizePrecondition describes a condition that must be true for the resize to take place
@@ -33,23 +34,46 @@ type ResizePrecondition struct {
 	ResourceVersion string
 }
 
+// A PreconditionError is returned when a replication controller fails to match
+// the resize preconditions passed to kubectl.
 type PreconditionError struct {
 	Precondition  string
 	ExpectedValue string
 	ActualValue   string
 }
 
-func (pe *PreconditionError) Error() string {
+func (pe PreconditionError) Error() string {
 	return fmt.Sprintf("Expected %s to be %s, was %s", pe.Precondition, pe.ExpectedValue, pe.ActualValue)
 }
 
+type ControllerResizeErrorType int
+
+const (
+	ControllerResizeGetFailure ControllerResizeErrorType = iota
+	ControllerResizeUpdateFailure
+)
+
+// A ControllerResizeError is returned when a the resize request passes
+// preconditions but fails to actually resize the controller.
+type ControllerResizeError struct {
+	FailureType     ControllerResizeErrorType
+	ResourceVersion string
+	ActualError     error
+}
+
+func (c ControllerResizeError) Error() string {
+	return fmt.Sprintf(
+		"Resizing the controller failed with: %s; Current resource version %s",
+		c.ActualError, c.ResourceVersion)
+}
+
 // Validate ensures that the preconditions match.  Returns nil if they are valid, an error otherwise
 func (precondition *ResizePrecondition) Validate(controller *api.ReplicationController) error {
 	if precondition.Size != -1 && controller.Spec.Replicas != precondition.Size {
-		return &PreconditionError{"replicas", strconv.Itoa(precondition.Size), strconv.Itoa(controller.Spec.Replicas)}
+		return PreconditionError{"replicas", strconv.Itoa(precondition.Size), strconv.Itoa(controller.Spec.Replicas)}
 	}
 	if precondition.ResourceVersion != "" && controller.ResourceVersion != precondition.ResourceVersion {
-		return &PreconditionError{"resource version", precondition.ResourceVersion, controller.ResourceVersion}
+		return PreconditionError{"resource version", precondition.ResourceVersion, controller.ResourceVersion}
 	}
 	return nil
 }
@@ -70,11 +94,27 @@ type ReplicationControllerResizer struct {
 	client.Interface
 }
 
+// ResizeCondition is a closure around Resize that facilitates retries via util.wait
+func ResizeCondition(r Resizer, precondition *ResizePrecondition, namespace, name string, count uint) wait.ConditionFunc {
+	return func() (bool, error) {
+		_, err := r.Resize(namespace, name, precondition, count)
+		switch e, _ := err.(ControllerResizeError); err.(type) {
+		case nil:
+			return true, nil
+		case ControllerResizeError:
+			if e.FailureType == ControllerResizeUpdateFailure {
+				return false, nil
+			}
+		}
+		return false, err
+	}
+}
+
 func (resize *ReplicationControllerResizer) Resize(namespace, name string, preconditions *ResizePrecondition, newSize uint) (string, error) {
 	rc := resize.ReplicationControllers(namespace)
 	controller, err := rc.Get(name)
 	if err != nil {
-		return "", err
+		return "", ControllerResizeError{ControllerResizeGetFailure, "Unknown", err}
 	}
 
 	if preconditions != nil {
@@ -86,7 +126,7 @@ func (resize *ReplicationControllerResizer) Resize(namespace, name string, preco
 	controller.Spec.Replicas = int(newSize)
 	// TODO: do retry on 409 errors here?
 	if _, err := rc.Update(controller); err != nil {
-		return "", err
+		return "", ControllerResizeError{ControllerResizeUpdateFailure, controller.ResourceVersion, err}
 	}
 	// TODO: do a better job of printing objects here.
 	return "resized", nil
diff --git a/pkg/kubectl/resize_test.go b/pkg/kubectl/resize_test.go
index 4e1da6c59a5..f0ea6888eae 100644
--- a/pkg/kubectl/resize_test.go
+++ b/pkg/kubectl/resize_test.go
@@ -17,14 +17,53 @@ limitations under the License.
 package kubectl
 
 import (
-	//	"strings"
+	"errors"
 	"testing"
 
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/api"
 	"github.com/GoogleCloudPlatform/kubernetes/pkg/client"
-	//	"github.com/GoogleCloudPlatform/kubernetes/pkg/util"
 )
 
+type ErrorReplicationControllers struct {
+	client.FakeReplicationControllers
+}
+
+func (c *ErrorReplicationControllers) Update(controller *api.ReplicationController) (*api.ReplicationController, error) {
+	return nil, errors.New("Replication controller update failure")
+}
+
+type ErrorReplicationControllerClient struct {
+	client.Fake
+}
+
+func (c *ErrorReplicationControllerClient) ReplicationControllers(namespace string) client.ReplicationControllerInterface {
+	return &ErrorReplicationControllers{client.FakeReplicationControllers{&c.Fake, namespace}}
+}
+
+func TestReplicationControllerResizeRetry(t *testing.T) {
+	fake := &ErrorReplicationControllerClient{Fake: client.Fake{}}
+	resizer := ReplicationControllerResizer{fake}
+	preconditions := ResizePrecondition{-1, ""}
+	count := uint(3)
+	name := "foo"
+	namespace := "default"
+
+	resizeFunc := ResizeCondition(&resizer, &preconditions, namespace, name, count)
+	pass, err := resizeFunc()
+	if pass != false {
+		t.Errorf("Expected an update failure to return pass = false, got pass = %v", pass)
+	}
+	if err != nil {
+		t.Errorf("Did not expect an error on update failure, got %v", err)
+	}
+	preconditions = ResizePrecondition{3, ""}
+	resizeFunc = ResizeCondition(&resizer, &preconditions, namespace, name, count)
+	pass, err = resizeFunc()
+	if err == nil {
+		t.Errorf("Expected error on precondition failure")
+	}
+}
+
 func TestReplicationControllerResize(t *testing.T) {
 	fake := &client.Fake{}
 	resizer := ReplicationControllerResizer{fake}
diff --git a/pkg/util/wait/wait_test.go b/pkg/util/wait/wait_test.go
index c54d5b267f6..1a41c85d3d8 100644
--- a/pkg/util/wait/wait_test.go
+++ b/pkg/util/wait/wait_test.go
@@ -68,6 +68,13 @@ func TestPoll(t *testing.T) {
 	if invocations == 0 {
 		t.Errorf("Expected at least one invocation, got zero")
 	}
+	expectedError := errors.New("Expected error")
+	f = ConditionFunc(func() (bool, error) {
+		return false, expectedError
+	})
+	if err := Poll(time.Microsecond, time.Microsecond, f); err == nil || err != expectedError {
+		t.Fatalf("Expected error %v, got none %v", expectedError, err)
+	}
 }
 
 func TestPollForever(t *testing.T) {