diff --git a/cmd/wirey/root.go b/cmd/wirey/root.go
index 721fbb4..26d8b3a 100644
--- a/cmd/wirey/root.go
+++ b/cmd/wirey/root.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"log"
 	"os"
+	"path/filepath"
 	"strings"
 
 	"github.com/influxdata/wirey/backend"
@@ -32,6 +33,13 @@ var rootCmd = &cobra.Command{
 			log.Fatal(err)
 		}
 
+		privKeyBaseDir := filepath.Dir(privateKeyPath)
+		if _, err := os.Stat(privKeyBaseDir); os.IsNotExist(err) {
+			if err := os.Mkdir(privKeyBaseDir, 0600); err != nil {
+				log.Fatal("Unable to create the base directory for the wirey private key: %s - %s", privKeyBaseDir, err.Error())
+			}
+		}
+
 		i, err := backend.NewInterface(b, ifname, fmt.Sprintf("%s:%s", endpoint, endpointPort), ipAddr, privateKeyPath)
 
 		if err != nil {