diff --git a/cmd/helm/init.go b/cmd/helm/init.go
index 425c10074..4be54e675 100644
--- a/cmd/helm/init.go
+++ b/cmd/helm/init.go
@@ -274,7 +274,7 @@ func (i *initCmd) run() error {
 				if err := installer.Upgrade(i.kubeClient, &i.opts); err != nil {
 					return fmt.Errorf("error when upgrading: %s", err)
 				}
-				if err := i.ping(); err != nil {
+				if err := i.ping(i.opts.SelectImage()); err != nil {
 					return err
 				}
 				fmt.Fprintln(i.out, "\nTiller (the Helm server-side component) has been upgraded to the current version.")
@@ -290,7 +290,7 @@ func (i *initCmd) run() error {
 					"For more information on securing your installation see: https://docs.helm.sh/using_helm/#securing-your-helm-installation")
 			}
 		}
-		if err := i.ping(); err != nil {
+		if err := i.ping(i.opts.SelectImage()); err != nil {
 			return err
 		}
 	} else {
@@ -301,13 +301,13 @@ func (i *initCmd) run() error {
 	return nil
 }
 
-func (i *initCmd) ping() error {
+func (i *initCmd) ping(image string) error {
 	if i.wait {
 		_, kubeClient, err := getKubeClient(settings.KubeContext, settings.KubeConfig)
 		if err != nil {
 			return err
 		}
-		if !watchTillerUntilReady(settings.TillerNamespace, kubeClient, settings.TillerConnectionTimeout) {
+		if !watchTillerUntilReady(settings.TillerNamespace, kubeClient, settings.TillerConnectionTimeout, image) {
 			return fmt.Errorf("tiller was not found. polling deadline exceeded")
 		}
 
@@ -439,7 +439,7 @@ func ensureRepoFileFormat(file string, out io.Writer) error {
 // want to wait before we call New().
 //
 // Returns true if it exists. If the timeout was reached and it could not find the pod, it returns false.
-func watchTillerUntilReady(namespace string, client kubernetes.Interface, timeout int64) bool {
+func watchTillerUntilReady(namespace string, client kubernetes.Interface, timeout int64, newImage string) bool {
 	deadlinePollingChan := time.NewTimer(time.Duration(timeout) * time.Second).C
 	checkTillerPodTicker := time.NewTicker(500 * time.Millisecond)
 	doneChan := make(chan bool)
@@ -448,8 +448,8 @@ func watchTillerUntilReady(namespace string, client kubernetes.Interface, timeou
 
 	go func() {
 		for range checkTillerPodTicker.C {
-			_, err := portforwarder.GetTillerPodName(client.CoreV1(), namespace)
-			if err == nil {
+			image, err := portforwarder.GetTillerPodImage(client.CoreV1(), namespace)
+			if err == nil && image == newImage {
 				doneChan <- true
 				break
 			}
diff --git a/cmd/helm/installer/install.go b/cmd/helm/installer/install.go
index c9ba1b0ca..6027fdba8 100644
--- a/cmd/helm/installer/install.go
+++ b/cmd/helm/installer/install.go
@@ -68,7 +68,7 @@ func Upgrade(client kubernetes.Interface, opts *Options) error {
 	if semverCompare(tillerImage) == -1 && !opts.ForceUpgrade {
 		return errors.New("current Tiller version is newer, use --force-upgrade to downgrade")
 	}
-	obj.Spec.Template.Spec.Containers[0].Image = opts.selectImage()
+	obj.Spec.Template.Spec.Containers[0].Image = opts.SelectImage()
 	obj.Spec.Template.Spec.Containers[0].ImagePullPolicy = opts.pullPolicy()
 	obj.Spec.Template.Spec.ServiceAccountName = opts.ServiceAccount
 	if _, err := client.ExtensionsV1beta1().Deployments(opts.Namespace).Update(obj); err != nil {
@@ -223,7 +223,7 @@ func generateDeployment(opts *Options) (*v1beta1.Deployment, error) {
 					Containers: []v1.Container{
 						{
 							Name:            "tiller",
-							Image:           opts.selectImage(),
+							Image:           opts.SelectImage(),
 							ImagePullPolicy: opts.pullPolicy(),
 							Ports: []v1.ContainerPort{
 								{ContainerPort: 44134, Name: "tiller"},
diff --git a/cmd/helm/installer/options.go b/cmd/helm/installer/options.go
index 729bdf20b..196ad8de4 100644
--- a/cmd/helm/installer/options.go
+++ b/cmd/helm/installer/options.go
@@ -99,7 +99,8 @@ type Options struct {
 	Values []string
 }
 
-func (opts *Options) selectImage() string {
+// SelectImage returns the image according to whether UseCanary is true or not
+func (opts *Options) SelectImage() string {
 	switch {
 	case opts.UseCanary:
 		return defaultImage + ":canary"
diff --git a/pkg/helm/portforwarder/portforwarder.go b/pkg/helm/portforwarder/portforwarder.go
index cc3261d1c..e962eef7f 100644
--- a/pkg/helm/portforwarder/portforwarder.go
+++ b/pkg/helm/portforwarder/portforwarder.go
@@ -54,6 +54,21 @@ func GetTillerPodName(client corev1.PodsGetter, namespace string) (string, error
 	return pod.ObjectMeta.GetName(), nil
 }
 
+// GetTillerPodImage fetches the image of tiller pod running in the given namespace.
+func GetTillerPodImage(client corev1.PodsGetter, namespace string) (string, error) {
+	selector := tillerPodLabels.AsSelector()
+	pod, err := getFirstRunningPod(client, namespace, selector)
+	if err != nil {
+		return "", err
+	}
+	for _, c := range pod.Spec.Containers {
+		if c.Name == "tiller" {
+			return c.Image, nil
+		}
+	}
+	return "", fmt.Errorf("could not find a tiller pod")
+}
+
 func getFirstRunningPod(client corev1.PodsGetter, namespace string, selector labels.Selector) (*v1.Pod, error) {
 	options := metav1.ListOptions{LabelSelector: selector.String()}
 	pods, err := client.Pods(namespace).List(options)