diff --git a/cmd/minikube/cmd/node_add.go b/cmd/minikube/cmd/node_add.go
index de1ce7f92d57..ab7e422a835a 100644
--- a/cmd/minikube/cmd/node_add.go
+++ b/cmd/minikube/cmd/node_add.go
@@ -64,7 +64,7 @@ var nodeAddCmd = &cobra.Command{
 		}
 
 		if err := node.Add(cc, n, false); err != nil {
-			_, err := maybeDeleteAndRetry(*cc, n, nil, err)
+			_, err := maybeDeleteAndRetry(cmd, *cc, n, nil, err)
 			if err != nil {
 				exit.WithError("failed to add node", err)
 			}
diff --git a/cmd/minikube/cmd/node_start.go b/cmd/minikube/cmd/node_start.go
index 47c6553ac2c7..bfc8431218ff 100644
--- a/cmd/minikube/cmd/node_start.go
+++ b/cmd/minikube/cmd/node_start.go
@@ -69,7 +69,7 @@ var nodeStartCmd = &cobra.Command{
 
 		_, err = node.Start(s, false)
 		if err != nil {
-			_, err := maybeDeleteAndRetry(*cc, *n, nil, err)
+			_, err := maybeDeleteAndRetry(cmd, *cc, *n, nil, err)
 			if err != nil {
 				node.MaybeExitWithAdvice(err)
 				exit.WithError("failed to start node", err)
diff --git a/cmd/minikube/cmd/start.go b/cmd/minikube/cmd/start.go
index c3029a63768c..cb109f852c13 100644
--- a/cmd/minikube/cmd/start.go
+++ b/cmd/minikube/cmd/start.go
@@ -200,7 +200,7 @@ func runStart(cmd *cobra.Command, args []string) {
 		}
 	}
 
-	kubeconfig, err := startWithDriver(starter, existing)
+	kubeconfig, err := startWithDriver(cmd, starter, existing)
 	if err != nil {
 		node.MaybeExitWithAdvice(err)
 		exit.WithError("failed to start node", err)
@@ -279,10 +279,10 @@ func provisionWithDriver(cmd *cobra.Command, ds registry.DriverState, existing *
 	}, nil
 }
 
-func startWithDriver(starter node.Starter, existing *config.ClusterConfig) (*kubeconfig.Settings, error) {
+func startWithDriver(cmd *cobra.Command, starter node.Starter, existing *config.ClusterConfig) (*kubeconfig.Settings, error) {
 	kubeconfig, err := node.Start(starter, true)
 	if err != nil {
-		kubeconfig, err = maybeDeleteAndRetry(*starter.Cfg, *starter.Node, starter.ExistingAddons, err)
+		kubeconfig, err = maybeDeleteAndRetry(cmd, *starter.Cfg, *starter.Node, starter.ExistingAddons, err)
 		if err != nil {
 			return nil, err
 		}
@@ -411,20 +411,22 @@ func showKubectlInfo(kcs *kubeconfig.Settings, k8sVersion string, machineName st
 	return nil
 }
 
-func maybeDeleteAndRetry(cc config.ClusterConfig, n config.Node, existingAddons map[string]bool, originalErr error) (*kubeconfig.Settings, error) {
+func maybeDeleteAndRetry(cmd *cobra.Command, existing config.ClusterConfig, n config.Node, existingAddons map[string]bool, originalErr error) (*kubeconfig.Settings, error) {
 	if viper.GetBool(deleteOnFailure) {
 		out.WarningT("Node {{.name}} failed to start, deleting and trying again.", out.V{"name": n.Name})
 		// Start failed, delete the cluster and try again
-		profile, err := config.LoadProfile(cc.Name)
+		profile, err := config.LoadProfile(existing.Name)
 		if err != nil {
-			out.ErrT(out.Meh, `"{{.name}}" profile does not exist, trying anyways.`, out.V{"name": cc.Name})
+			out.ErrT(out.Meh, `"{{.name}}" profile does not exist, trying anyways.`, out.V{"name": existing.Name})
 		}
 
 		err = deleteProfile(profile)
 		if err != nil {
-			out.WarningT("Failed to delete cluster {{.name}}, proceeding with retry anyway.", out.V{"name": cc.Name})
+			out.WarningT("Failed to delete cluster {{.name}}, proceeding with retry anyway.", out.V{"name": existing.Name})
 		}
 
+		// Re-generate the cluster config, just in case the failure was related to an old config format
+		cc := updateExistingConfigFromFlags(cmd, &existing)
 		var kubeconfig *kubeconfig.Settings
 		for _, n := range cc.Nodes {
 			r, p, m, h, err := node.Provision(&cc, &n, n.ControlPlane, false)
diff --git a/cmd/minikube/cmd/start_flags.go b/cmd/minikube/cmd/start_flags.go
index c24bd6fad5db..c6a448d021ab 100644
--- a/cmd/minikube/cmd/start_flags.go
+++ b/cmd/minikube/cmd/start_flags.go
@@ -217,7 +217,7 @@ func ClusterFlagValue() string {
 // generateClusterConfig generate a config.ClusterConfig based on flags or existing cluster config
 func generateClusterConfig(cmd *cobra.Command, existing *config.ClusterConfig, k8sVersion string, drvName string) (config.ClusterConfig, config.Node, error) {
 	var cc config.ClusterConfig
-	if existing != nil { // create profile config first time
+	if existing != nil {
 		cc = updateExistingConfigFromFlags(cmd, existing)
 	} else {
 		glog.Info("no existing cluster config was found, will generate one from the flags ")