diff --git a/builder/vsphere/common/step_remote_upload.go b/builder/vsphere/common/step_remote_upload.go
index 8a0a872a7..9df7668e3 100644
--- a/builder/vsphere/common/step_remote_upload.go
+++ b/builder/vsphere/common/step_remote_upload.go
@@ -69,8 +69,11 @@ func (s *StepRemoteUpload) uploadFile(path string, d driver.Driver, ui packer.Ui
 
 	ui.Say(fmt.Sprintf("Uploading %s to %s", filename, remotePath))
 
-	if err := ds.MakeDirectory(remoteDirectory); err != nil {
-		return "", err
+	if exists := ds.DirExists(remotePath); exists == false {
+		log.Printf("Remote directory doesn't exist; creating...")
+		if err := ds.MakeDirectory(remoteDirectory); err != nil {
+			return "", err
+		}
 	}
 
 	if err := ds.UploadFile(path, remotePath, s.Host, s.SetHostForDatastoreUploads); err != nil {
diff --git a/builder/vsphere/driver/datastore.go b/builder/vsphere/driver/datastore.go
index f8eaf6eaf..adc13447f 100644
--- a/builder/vsphere/driver/datastore.go
+++ b/builder/vsphere/driver/datastore.go
@@ -16,6 +16,7 @@ import (
 type Datastore interface {
 	Info(params ...string) (*mo.Datastore, error)
 	FileExists(path string) bool
+	DirExists(path string) bool
 	Name() string
 	ResolvePath(path string) string
 	UploadFile(src, dst, host string, setHost bool) error
@@ -102,6 +103,14 @@ func (ds *DatastoreDriver) Info(params ...string) (*mo.Datastore, error) {
 	return &info, nil
 }
 
+func (ds *DatastoreDriver) DirExists(filepath string) bool {
+	_, err := ds.ds.Stat(ds.driver.ctx, filepath)
+	if _, ok := err.(object.DatastoreNoSuchDirectoryError); ok {
+		return false
+	}
+	return true
+}
+
 func (ds *DatastoreDriver) FileExists(path string) bool {
 	_, err := ds.ds.Stat(ds.driver.ctx, path)
 	return err == nil
diff --git a/builder/vsphere/driver/datastore_mock.go b/builder/vsphere/driver/datastore_mock.go
index 889dd254a..28757ee83 100644
--- a/builder/vsphere/driver/datastore_mock.go
+++ b/builder/vsphere/driver/datastore_mock.go
@@ -37,6 +37,9 @@ func (ds *DatastoreMock) FileExists(path string) bool {
 	return ds.FileExistsReturn
 }
 
+func (ds *DatastoreMock) DirExists(path string) bool {
+	return true
+}
 func (ds *DatastoreMock) Name() string {
 	if ds.NameReturn == "" {
 		return "datastore-mock"