diff --git a/pkg/minikube/assets/addons.go b/pkg/minikube/assets/addons.go
index 604b0109ae83..b6db690e76fa 100644
--- a/pkg/minikube/assets/addons.go
+++ b/pkg/minikube/assets/addons.go
@@ -302,14 +302,15 @@ func addMinikubeDirToAssets(basedir, vmpath string, assets *[]CopyableFile) erro
 			return errors.Wrapf(err, "checking if %s is directory", hostpath)
 		}
 		if !isDir {
-			if vmpath == "" {
+			vmdir := vmpath
+			if vmdir == "" {
 				rPath, err := filepath.Rel(basedir, hostpath)
 				if err != nil {
 					return errors.Wrap(err, "generating relative path")
 				}
 				rPath = filepath.Dir(rPath)
 				rPath = filepath.ToSlash(rPath)
-				vmpath = path.Join("/", rPath)
+				vmdir = path.Join("/", rPath)
 			}
 			permString := fmt.Sprintf("%o", info.Mode().Perm())
 			// The conversion will strip the leading 0 if present, so add it back
@@ -318,7 +319,7 @@ func addMinikubeDirToAssets(basedir, vmpath string, assets *[]CopyableFile) erro
 				permString = fmt.Sprintf("0%s", permString)
 			}
 
-			f, err := NewFileAsset(hostpath, vmpath, filepath.Base(hostpath), permString)
+			f, err := NewFileAsset(hostpath, vmdir, filepath.Base(hostpath), permString)
 			if err != nil {
 				return errors.Wrapf(err, "creating file asset for %s", hostpath)
 			}
diff --git a/pkg/minikube/assets/addons_test.go b/pkg/minikube/assets/addons_test.go
new file mode 100644
index 000000000000..bfd8bfeeeaef
--- /dev/null
+++ b/pkg/minikube/assets/addons_test.go
@@ -0,0 +1,159 @@
+/*
+Copyright 2016 The Kubernetes Authors All rights reserved.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+package assets
+
+import (
+	"io/ioutil"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/google/go-cmp/cmp"
+	"k8s.io/minikube/pkg/minikube/constants"
+)
+
+func setupTestDir() (string, error) {
+	path, err := ioutil.TempDir("", "minipath")
+	if err != nil {
+		return "", err
+	}
+
+	os.Setenv(constants.MinikubeHome, path)
+	return path, err
+}
+
+func TestAddMinikubeDirAssets(t *testing.T) {
+
+	tests := []struct {
+		description string
+		baseDir     string
+		files       []struct {
+			relativePath string
+			expectedPath string
+		}
+		vmPath      string
+		expectedCfg string
+	}{
+		{
+			description: "relative path assets",
+			baseDir:     "/files",
+			files: []struct {
+				relativePath string
+				expectedPath string
+			}{
+				{
+					relativePath: "/dir1/file1.txt",
+					expectedPath: constants.AddonsPath,
+				},
+				{
+					relativePath: "/dir1/file2.txt",
+					expectedPath: constants.AddonsPath,
+				},
+				{
+					relativePath: "/dir2/file1.txt",
+					expectedPath: constants.AddonsPath,
+				},
+			},
+			vmPath: constants.AddonsPath,
+		},
+		{
+			description: "absolute path assets",
+			baseDir:     "/files",
+			files: []struct {
+				relativePath string
+				expectedPath string
+			}{
+				{
+					relativePath: "/dir1/file1.txt",
+					expectedPath: "/dir1",
+				},
+				{
+					relativePath: "/dir1/file2.txt",
+					expectedPath: "/dir1",
+				},
+				{
+					relativePath: "/dir2/file1.txt",
+					expectedPath: "/dir2",
+				},
+			},
+			vmPath: "",
+		},
+	}
+	var testDirs = make([]string, 0)
+	defer func() {
+		for _, testDir := range testDirs {
+			err := os.RemoveAll(testDir)
+			if err != nil {
+				t.Logf("got unexpected error removing test dir: %v", err)
+			}
+		}
+	}()
+
+	for _, test := range tests {
+		t.Run(test.description, func(t *testing.T) {
+			testDir, err := setupTestDir()
+			if err != nil {
+				t.Errorf("got unexpected error creating test dir: %v", err)
+				return
+			}
+
+			testDirs = append(testDirs, testDir)
+			testFileBaseDir := filepath.Join(testDir, test.baseDir)
+			want := make(map[string]string, 0)
+			for _, fileDef := range test.files {
+				err := func() error {
+					path := filepath.Join(testFileBaseDir, fileDef.relativePath)
+					err := os.MkdirAll(filepath.Dir(path), 0755)
+					want[path] = fileDef.expectedPath
+					if err != nil {
+						return err
+					}
+
+					file, err := os.Create(path)
+					if err != nil {
+						return err
+					}
+
+					defer file.Close()
+
+					_, err = file.WriteString("test")
+					return err
+				}()
+				if err != nil {
+					t.Errorf("unable to create file on fs: %v", err)
+					return
+				}
+			}
+
+			var actualFiles []CopyableFile
+			err = addMinikubeDirToAssets(testFileBaseDir, test.vmPath, &actualFiles)
+			if err != nil {
+				t.Errorf("got unexpected error adding minikube dir assets: %v", err)
+				return
+			}
+
+			got := make(map[string]string, 0)
+			for _, actualFile := range actualFiles {
+				got[actualFile.GetAssetName()] = actualFile.GetTargetDir()
+			}
+			if diff := cmp.Diff(want, got); diff != "" {
+				t.Errorf("files differ: (-want +got)\n%s", diff)
+			}
+		})
+	}
+
+}