diff --git a/command/hcl2_upgrade.go b/command/hcl2_upgrade.go
index c8a906f68..5e0a8b1a3 100644
--- a/command/hcl2_upgrade.go
+++ b/command/hcl2_upgrade.go
@@ -133,7 +133,7 @@ type BlockParser interface {
 
 func (c *HCL2UpgradeCommand) RunContext(_ context.Context, cla *HCL2UpgradeArgs) int {
 	var output io.Writer
-	if err := os.MkdirAll(filepath.Dir(cla.OutputFile), 0); err != nil {
+	if err := os.MkdirAll(filepath.Dir(cla.OutputFile), 0755); err != nil {
 		c.Ui.Error(fmt.Sprintf("Failed to create output directory: %v", err))
 		return 1
 	}
diff --git a/provisioner/file/provisioner_test.go b/provisioner/file/provisioner_test.go
index 428443bdc..a8cb9de5b 100644
--- a/provisioner/file/provisioner_test.go
+++ b/provisioner/file/provisioner_test.go
@@ -340,6 +340,14 @@ func TestProvisionerProvision_DownloadsMultipleFilesToFolder(t *testing.T) {
 		"direction":   "download",
 	}
 
+	// Cleaning up destination directory
+	cwd, err := os.Getwd()
+	if err != nil {
+		t.Fatalf("Failed getting current working directory")
+	}
+	destinationDir := filepath.Join(cwd, "something")
+	defer os.RemoveAll(destinationDir)
+
 	if err := p.Prepare(config); err != nil {
 		t.Fatalf("err: %s", err)
 	}