diff --git a/cmd/minikube/cmd/start.go b/cmd/minikube/cmd/start.go
index d9c9cb5f5633..fbeb406e89ac 100644
--- a/cmd/minikube/cmd/start.go
+++ b/cmd/minikube/cmd/start.go
@@ -105,6 +105,7 @@ const (
 	hostDNSResolver       = "host-dns-resolver"
 	waitUntilHealthy      = "wait"
 	force                 = "force"
+	interactive           = "interactive"
 	waitTimeout           = "wait-timeout"
 	nativeSSH             = "native-ssh"
 )
@@ -140,6 +141,7 @@ func initMinikubeFlags() {
 	viper.AutomaticEnv()
 
 	startCmd.Flags().Bool(force, false, "Force minikube to perform possibly dangerous operations")
+	startCmd.Flags().Bool(interactive, true, "Allow user prompts for more information")
 
 	startCmd.Flags().Int(cpus, constants.DefaultCPUS, "Number of CPUs allocated to the minikube VM.")
 	startCmd.Flags().String(memory, constants.DefaultMemorySize, "Amount of RAM allocated to the minikube VM (format: <number>[<unit>], where unit = b, k, m or g).")
@@ -290,7 +292,16 @@ func runStart(cmd *cobra.Command, args []string) {
 
 	validateFlags(driver)
 	validateUser(driver)
-	installOrUpdateDriver(driver)
+
+	v, err := version.GetSemverVersion()
+	if err != nil {
+		out.WarningT("Error parsing minikube version: {{.error}}", out.V{"error": err})
+	} else {
+		if err := drivers.InstallOrUpdate(driver, constants.MakeMiniPath("bin"), v, viper.GetBool(interactive)); err != nil {
+			glog.Errorf("error: %v", err)
+			out.WarningT("Unable to update {{.driver}} driver: {{.error}}", out.V{"driver": driver, "error": err})
+		}
+	}
 
 	k8sVersion, isUpgrade := getKubernetesVersion(oldConfig)
 	config, err := generateCfgFromFlags(cmd, k8sVersion, driver)
@@ -1055,27 +1066,3 @@ func configureMounts() {
 func saveConfig(clusterCfg *cfg.Config) error {
 	return cfg.CreateProfile(viper.GetString(cfg.MachineProfile), clusterCfg)
 }
-
-func installOrUpdateDriver(driver string) {
-	var driverExecutable string
-	switch driver {
-	case constants.DriverKvm2:
-		driverExecutable = fmt.Sprintf("docker-machine-driver-%s", constants.DriverKvm2)
-	case constants.DriverHyperkit:
-		driverExecutable = fmt.Sprintf("docker-machine-driver-%s", constants.DriverHyperkit)
-	default: // driver doesn't install or update
-		return
-	}
-
-	minikubeVersion, err := version.GetSemverVersion()
-	if err != nil {
-		out.WarningT("Error parsing minikube version: {{.error}}", out.V{"error": err})
-		return
-	}
-
-	targetDir := constants.MakeMiniPath("bin")
-	err = drivers.InstallOrUpdate(driverExecutable, targetDir, minikubeVersion)
-	if err != nil {
-		out.WarningT("Error downloading driver: {{.error}}", out.V{"error": err})
-	}
-}
diff --git a/pkg/drivers/drivers.go b/pkg/drivers/drivers.go
index 52913dc925ee..da7edaf2d833 100644
--- a/pkg/drivers/drivers.go
+++ b/pkg/drivers/drivers.go
@@ -22,7 +22,6 @@ import (
 	"io/ioutil"
 	"os"
 	"os/exec"
-	"path"
 	"path/filepath"
 	"regexp"
 	"strings"
@@ -38,6 +37,7 @@ import (
 	"github.com/pkg/errors"
 	"k8s.io/minikube/pkg/version"
 
+	"k8s.io/minikube/pkg/minikube/constants"
 	"k8s.io/minikube/pkg/minikube/out"
 	"k8s.io/minikube/pkg/util"
 )
@@ -123,14 +123,14 @@ func MakeDiskImage(d *drivers.BaseDriver, boot2dockerURL string, diskSize int) e
 			return errors.Wrapf(err, "createRawDiskImage(%s)", diskPath)
 		}
 		machPath := d.ResolveStorePath(".")
-		if err := fixPermissions(machPath); err != nil {
+		if err := fixMachinePermissions(machPath); err != nil {
 			return errors.Wrapf(err, "fixing permissions on %s", machPath)
 		}
 	}
 	return nil
 }
 
-func fixPermissions(path string) error {
+func fixMachinePermissions(path string) error {
 	glog.Infof("Fixing permissions on %s ...", path)
 	if err := os.Chown(path, syscall.Getuid(), syscall.Getegid()); err != nil {
 		return errors.Wrap(err, "chown dir")
@@ -149,44 +149,95 @@ func fixPermissions(path string) error {
 }
 
 // InstallOrUpdate downloads driver if it is not present, or updates it if there's a newer version
-func InstallOrUpdate(driver, destination string, v semver.Version) error {
-	glog.Infof("InstallOrUpdate(%s): dest=%s, version=%s, PATH=%s", driver, destination, v, os.Getenv("PATH"))
+func InstallOrUpdate(driver string, directory string, v semver.Version, interactive bool) error {
+	if driver != constants.DriverKvm2 && driver != constants.DriverHyperkit {
+		return nil
+	}
 
-	_, err := exec.LookPath(driver)
-	// if file driver doesn't exist, download it
+	executable := fmt.Sprintf("docker-machine-driver-%s", driver)
+	path, err := validateDriver(executable, v)
 	if err != nil {
-		glog.Infof("LookPath %s: %v", driver, err)
-		return download(driver, v, destination)
+		glog.Warningf("%s: %v", executable, err)
+		path = filepath.Join(directory, executable)
+		derr := download(executable, path, v)
+		if derr != nil {
+			return derr
+		}
+	}
+	return fixDriverPermissions(driver, path, interactive)
+}
+
+// fixDriverPermissions fixes the permissions on a driver
+func fixDriverPermissions(driver string, path string, interactive bool) error {
+	// This method only supports hyperkit so far (because it's complicated)
+	if driver != constants.DriverHyperkit {
+		return nil
 	}
 
-	cmd := exec.Command(driver, "version")
-	output, err := cmd.Output()
-	// if driver doesnt support 'version', it is old, download it
+	// Using the find command for hyperkit is far easier than cross-platform uid checks in Go.
+	stdout, err := exec.Command("find", path, "-uid", "0", "-perm", "4755").Output()
+	glog.Infof("stdout: %s", stdout)
+	if err == nil && strings.TrimSpace(string(stdout)) == path {
+		glog.Infof("%s looks good", path)
+		return nil
+	}
+
+	cmds := []*exec.Cmd{
+		exec.Command("sudo", "chown", "root:wheel", path),
+		exec.Command("sudo", "chmod", "u+s", path),
+	}
+
+	var example strings.Builder
+	for _, c := range cmds {
+		example.WriteString(fmt.Sprintf("    $ %s \n", strings.Join(c.Args, " ")))
+	}
+
+	out.T(out.Permissions, "The '{{.driver}}' driver requires elevated permissions. The following commands will be executed:\n\n{{ .example }}\n", out.V{"driver": driver, "example": example.String()})
+	for _, c := range cmds {
+		testArgs := append([]string{"-n"}, c.Args[1:]...)
+		test := exec.Command("sudo", testArgs...)
+		glog.Infof("testing: %v", test.Args)
+		if err := test.Run(); err != nil {
+			glog.Infof("%v may require a password: %v", c.Args, err)
+			if !interactive {
+				return fmt.Errorf("%v requires a password, and --interactive=false", c.Args)
+			}
+		}
+		glog.Infof("running: %v", c.Args)
+		err := c.Run()
+		if err != nil {
+			return errors.Wrapf(err, "%v", c.Args)
+		}
+	}
+	return nil
+}
+
+// validateDriver validates if a driver appears to be up-to-date and installed properly
+func validateDriver(driver string, v semver.Version) (string, error) {
+	glog.Infof("Validating %s, PATH=%s", driver, os.Getenv("PATH"))
+	path, err := exec.LookPath(driver)
 	if err != nil {
-		glog.Infof("%s version: %v", driver, err)
-		return download(driver, v, destination)
+		return path, err
 	}
 
-	ev := ExtractVMDriverVersion(string(output))
+	output, err := exec.Command(path, "version").Output()
+	if err != nil {
+		return path, err
+	}
 
-	// if the driver doesn't return any version, download it
+	ev := extractVMDriverVersion(string(output))
 	if len(ev) == 0 {
-		glog.Infof("%s: unable to extract version from %q", driver, output)
-		return download(driver, v, destination)
+		return path, fmt.Errorf("%s: unable to extract version from %q", driver, output)
 	}
 
 	vmDriverVersion, err := semver.Make(ev)
 	if err != nil {
-		return errors.Wrap(err, "can't parse driver version")
+		return path, errors.Wrap(err, "can't parse driver version")
 	}
-
-	// if the current driver version is older, download newer
 	if vmDriverVersion.LT(v) {
-		glog.Infof("%s is version %s, want %s", driver, vmDriverVersion, v)
-		return download(driver, v, destination)
+		return path, fmt.Errorf("%s is version %s, want %s", driver, vmDriverVersion, v)
 	}
-
-	return nil
+	return path, nil
 }
 
 func driverWithChecksumURL(driver string, v semver.Version) string {
@@ -194,50 +245,32 @@ func driverWithChecksumURL(driver string, v semver.Version) string {
 	return fmt.Sprintf("%s?checksum=file:%s.sha256", base, base)
 }
 
-func download(driver string, v semver.Version, destination string) error {
-	// supports kvm2 and hyperkit
-	if driver != "docker-machine-driver-kvm2" && driver != "docker-machine-driver-hyperkit" {
-		return nil
-	}
-
+// download an arbitrary driver
+func download(driver string, destination string, v semver.Version) error {
 	out.T(out.FileDownload, "Downloading driver {{.driver}}:", out.V{"driver": driver})
-	targetFilepath := path.Join(destination, driver)
-	os.Remove(targetFilepath)
+	os.Remove(destination)
 	url := driverWithChecksumURL(driver, v)
 	client := &getter.Client{
 		Src:     url,
-		Dst:     targetFilepath,
+		Dst:     destination,
 		Mode:    getter.ClientModeFile,
 		Options: []getter.ClientOption{getter.WithProgress(util.DefaultProgressBar)},
 	}
 
 	glog.Infof("Downloading: %+v", client)
-
 	if err := client.Get(); err != nil {
 		return errors.Wrapf(err, "download failed: %s", url)
 	}
-
-	err := os.Chmod(targetFilepath, 0755)
-	if err != nil {
-		return errors.Wrap(err, "chmod error")
-	}
-
-	if driver == "docker-machine-driver-hyperkit" {
-		err := setHyperKitPermissions(targetFilepath)
-		if err != nil {
-			return errors.Wrap(err, "setting hyperkit permission")
-		}
-	}
-
-	return nil
+	// Give downloaded drivers a baseline decent file permission
+	return os.Chmod(destination, 0755)
 }
 
-// ExtractVMDriverVersion extracts the driver version.
+// extractVMDriverVersion extracts the driver version.
 // KVM and Hyperkit drivers support the 'version' command, that display the information as:
 // version: vX.X.X
 // commit: XXXX
 // This method returns the version 'vX.X.X' or empty if the version isn't found.
-func ExtractVMDriverVersion(s string) string {
+func extractVMDriverVersion(s string) string {
 	versionRegex := regexp.MustCompile(`version:(.*)`)
 	matches := versionRegex.FindStringSubmatch(s)
 
@@ -248,22 +281,3 @@ func ExtractVMDriverVersion(s string) string {
 	v := strings.TrimSpace(matches[1])
 	return strings.TrimPrefix(v, version.VersionPrefix)
 }
-
-func setHyperKitPermissions(driverPath string) error {
-	msg := fmt.Sprintf("A new hyperkit driver was installed. It needs elevated permissions to run. The following commands will be executed:\n\n    $ sudo chown root:wheel %s\n    $ sudo chmod u+s %s\n", driverPath, driverPath)
-	out.T(out.Permissions, msg, out.V{})
-
-	cmd := exec.Command("sudo", "chown", "root:wheel", driverPath)
-	err := cmd.Run()
-	if err != nil {
-		return errors.Wrap(err, "chown root:wheel")
-	}
-
-	cmd = exec.Command("sudo", "chmod", "u+s", driverPath)
-	err = cmd.Run()
-	if err != nil {
-		return errors.Wrap(err, "chmod u+s")
-	}
-
-	return nil
-}
diff --git a/pkg/drivers/drivers_test.go b/pkg/drivers/drivers_test.go
index c4d9aafe03b0..10e42e3e4466 100644
--- a/pkg/drivers/drivers_test.go
+++ b/pkg/drivers/drivers_test.go
@@ -50,24 +50,24 @@ func Test_createDiskImage(t *testing.T) {
 }
 
 func TestExtractVMDriverVersion(t *testing.T) {
-	v := ExtractVMDriverVersion("")
+	v := extractVMDriverVersion("")
 	if len(v) != 0 {
 		t.Error("Expected empty string")
 	}
 
-	v = ExtractVMDriverVersion("random text")
+	v = extractVMDriverVersion("random text")
 	if len(v) != 0 {
 		t.Error("Expected empty string")
 	}
 
 	expectedVersion := "1.2.3"
 
-	v = ExtractVMDriverVersion("version: v1.2.3")
+	v = extractVMDriverVersion("version: v1.2.3")
 	if expectedVersion != v {
 		t.Errorf("Expected version: %s, got: %s", expectedVersion, v)
 	}
 
-	v = ExtractVMDriverVersion("version: 1.2.3")
+	v = extractVMDriverVersion("version: 1.2.3")
 	if expectedVersion != v {
 		t.Errorf("Expected version: %s, got: %s", expectedVersion, v)
 	}
diff --git a/pkg/minikube/out/style.go b/pkg/minikube/out/style.go
index 44ae64efe8f6..4791787413b6 100644
--- a/pkg/minikube/out/style.go
+++ b/pkg/minikube/out/style.go
@@ -78,7 +78,7 @@ var styles = map[StyleEnum]style{
 	Documentation: {Prefix: "📘  "},
 	Issues:        {Prefix: "⁉️   "},
 	Issue:         {Prefix: "    ▪ ", LowPrefix: lowIndent}, // Indented bullet
-	Check:         {Prefix: "✔️  "},
+	Check:         {Prefix: "✅  "},
 	Celebration:   {Prefix: "🎉  "},
 	Workaround:    {Prefix: "👉  ", LowPrefix: lowIndent},
 
diff --git a/test/integration/driver_install_or_update_test.go b/test/integration/driver_install_or_update_test.go
index 682b872d0c13..de11940873cb 100644
--- a/test/integration/driver_install_or_update_test.go
+++ b/test/integration/driver_install_or_update_test.go
@@ -84,7 +84,7 @@ func TestKVMDriverInstallOrUpdate(t *testing.T) {
 			t.Fatalf("Expected new semver. test: %v, got: %v", tc.name, err)
 		}
 
-		err = drivers.InstallOrUpdate("docker-machine-driver-kvm2", dir, newerVersion)
+		err = drivers.InstallOrUpdate("kvm2", dir, newerVersion, true)
 		if err != nil {
 			t.Fatalf("Failed to update driver to %v. test: %s, got: %v", newerVersion, tc.name, err)
 		}
@@ -147,7 +147,7 @@ func TestHyperKitDriverInstallOrUpdate(t *testing.T) {
 			t.Fatalf("Expected new semver. test: %v, got: %v", tc.name, err)
 		}
 
-		err = drivers.InstallOrUpdate("docker-machine-driver-hyperkit", dir, newerVersion)
+		err = drivers.InstallOrUpdate("hyperkit", dir, newerVersion, true)
 		if err != nil {
 			t.Fatalf("Failed to update driver to %v. test: %s, got: %v", newerVersion, tc.name, err)
 		}