diff -u b/core/modules/migrate/src/Plugin/migrate/destination/EntityFile.php b/core/modules/migrate/src/Plugin/migrate/destination/EntityFile.php
--- b/core/modules/migrate/src/Plugin/migrate/destination/EntityFile.php
+++ b/core/modules/migrate/src/Plugin/migrate/destination/EntityFile.php
@@ -95,7 +95,7 @@
 
     $replace = $this->getOverwriteMode($row);
     $success = $this->writeFile($source, $destination, $replace);
-    if (empty($success)) {
+    if (!$success) {
       $dir = $this->getDirectory($destination);
       if (file_prepare_directory($dir, FILE_CREATE_DIRECTORY)) {
         $success = $this->writeFile($source, $destination, $replace);
reverted:
--- b/core/modules/migrate_drupal/src/Plugin/migrate/process/d6/FileUri.php
+++ a/core/modules/migrate_drupal/src/Plugin/migrate/process/d6/FileUri.php
@@ -24,6 +24,7 @@
    * {@inheritdoc}
    */
   public function transform($value, MigrateExecutableInterface $migrate_executable, Row $row, $destination_property) {
+
     list($filepath, $file_directory_path, $temp_directory_path, $is_public) = $value;
 
     // Specific handling using $temp_directory_path for temporary files.