I found the answer [here][1]: - If the install uses FTP for updates (and prompts for credentials), automatic updates are disabled. (I found [this answer][2] which will tell you how to avoid using FTP.) - If the install is running as a SVN or GIT checkout, automatic updates are disabled - If the constants DISALLOW_FILE_MODS or AUTOMATIC_UPDATER_DISABLED are defined, automatic updates are disabled - If the constant WP_AUTO_UPDATE_CORE is defined as false, automatic updates are disabled - Your WordPress install also needs to be able to contact WordPress.org over HTTPS connections, so your PHP install also needs OpenSSL installed and working - Wp-Cron needs to be operational, if for some reason cron fails to work for your install, Automatic Updates will also be unavailable [This plugin][3] will test these things for you. [1]: http://make.wordpress.org/core/2013/09/24/automatic-core-updates/ [2]: https://wordpress.stackexchange.com/a/23175/4661 [3]: http://wordpress.org/plugins/background-update-tester/