Update: nowaydays, the more obvious solution is to make sure WP-CLI’s installed and then run
wp plugin update --all regularly, as a cron job.
Using Jetpack, Of Course!
All it takes, after installing the plugin and connecting to your WordPress.com account, is:
- On WordPress.com, select (beneath ‘My Sites’) the WordPress installation you’re looking to edit.
- Choose ‘Plugins’.
- Check ‘Autoupdates’ for every plugin.
For popular ‘premium’ plugins like WPML or Gravity Forms, this results in a ‘This plugin is not in the WordPress.org plugin repository, so we can’t autoupdate it.’ Good thing you don’t actually have to use them.