The WordPress automatic updates have been blocked on this site lately. This was intentional because updates turn off a plugin which is necessary for the design of the site. However, the last two updates on WordPress were security and bug fixes. More important, WordPress 3.9 is ready to drop either tonight or tomorrow. I’d love to see the site automatically updated to see how well it works.
Digital Ocean droplets require permission changes for the automatic update to function.
sudo chgrp -R www-data /path/to/www
sudo chmod -R g+w /path/to/www