This is not particular to the Drupal site but is caused by the hosting (local Vagrant) environment's PHP configuration. Try increasing these values in php.ini: upload_max_filesize = 64M post_max_size = 64M memory_limit = 64M **NOTE**: If you are using Webform for anonymous file upload to your site and you are setting high limits on file size like this you are quickly going to fill up a lot of disk space (most likely with spam). **NOTE**: After modifying php.ini file(s), you need to restart your HTTP server to use new configuration See answer on [Stackoverflow][1]. [1]: https://stackoverflow.com/questions/2184513/php-change-the-maximum-upload-file-size