diff --git a/pkg/minikube/machine/filesync_test.go b/pkg/minikube/machine/filesync_test.go
index 9eb7541cbe81..bd4f7d981deb 100644
--- a/pkg/minikube/machine/filesync_test.go
+++ b/pkg/minikube/machine/filesync_test.go
@@ -46,18 +46,9 @@ func TestAssetsFromDir(t *testing.T) {
 				relativePath string
 				expectedPath string
 			}{
-				{
-					relativePath: "/dir1/file1.txt",
-					expectedPath: vmpath.GuestAddonsDir,
-				},
-				{
-					relativePath: "/dir1/file2.txt",
-					expectedPath: vmpath.GuestAddonsDir,
-				},
-				{
-					relativePath: "/dir2/file1.txt",
-					expectedPath: vmpath.GuestAddonsDir,
-				},
+				{relativePath: "/dir1/file1.txt", expectedPath: vmpath.GuestAddonsDir},
+				{relativePath: "/dir1/file2.txt", expectedPath: vmpath.GuestAddonsDir},
+				{relativePath: "/dir2/file1.txt", expectedPath: vmpath.GuestAddonsDir},
 			},
 			vmPath: vmpath.GuestAddonsDir,
 		},
@@ -69,27 +60,18 @@ func TestAssetsFromDir(t *testing.T) {
 				relativePath string
 				expectedPath string
 			}{
-				{
-					relativePath: "/dir1/file1.txt",
-					expectedPath: "/dir1",
-				},
-				{
-					relativePath: "/dir1/file2.txt",
-					expectedPath: "/dir1",
-				},
-				{
-					relativePath: "/dir2/file1.txt",
-					expectedPath: "/dir2",
-				},
+				{relativePath: "/dir1/file1.txt", expectedPath: "/dir1"},
+				{relativePath: "/dir1/file2.txt", expectedPath: "/dir1"},
+				{relativePath: "/dir2/file1.txt", expectedPath: "/dir2"},
 			},
 			vmPath: "/",
 		},
 	}
-	var testDirs = make([]string, 0)
+
+	var testDirs []string
 	defer func() {
 		for _, testDir := range testDirs {
-			err := os.RemoveAll(testDir)
-			if err != nil {
+			if err := os.RemoveAll(testDir); err != nil {
 				t.Logf("got unexpected error removing test dir: %v", err)
 			}
 		}
@@ -98,18 +80,16 @@ func TestAssetsFromDir(t *testing.T) {
 	for _, test := range tests {
 		t.Run(test.description, func(t *testing.T) {
 			testDir := testutil.MakeTempDir(t)
-
 			testDirs = append(testDirs, testDir)
 			testFileBaseDir := filepath.Join(testDir, test.baseDir)
 			want := make(map[string]string)
 			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 {
+					if err := os.MkdirAll(filepath.Dir(path), 0o755); err != nil {
 						return err
 					}
+					want[path] = fileDef.expectedPath
 
 					file, err := os.Create(path)
 					if err != nil {
@@ -122,17 +102,24 @@ func TestAssetsFromDir(t *testing.T) {
 					return err
 				}()
 				if err != nil {
-					t.Errorf("unable to create file on fs: %v", err)
-					return
+					t.Fatalf("unable to create file on fs: %v", err)
 				}
 			}
 
 			actualFiles, err := assetsFromDir(testFileBaseDir, test.vmPath, test.flatten)
 			if err != nil {
-				t.Errorf("got unexpected error adding minikube dir assets: %v", err)
-				return
+				t.Fatalf("got unexpected error adding minikube dir assets: %v", err)
 			}
 
+			// Ensure file descriptors opened by assets.NewFileAsset are released (critical on Windows).
+			t.Cleanup(func() {
+				for _, f := range actualFiles {
+					if cerr := f.Close(); cerr != nil {
+						t.Logf("warning: closing asset %s failed: %v", f.GetSourcePath(), cerr)
+					}
+				}
+			})
+
 			got := make(map[string]string)
 			for _, actualFile := range actualFiles {
 				got[actualFile.GetSourcePath()] = actualFile.GetTargetDir()