Hello @noizepro,
Thanks for the feedback. Please keep in mind that the Plugins section is govern by WordPress itself. It actually connects to the respective plugin author’s repository to check for any latest versions. Any out dated plugin will trigger WordPress to display the message that the plugin is out dated and there is a new update. Yes, you can automatically if you have installed a free plugin. For bundled plugins, you won’t be able to update because you will not have access to the plugin update. When you validate your theme, you can update the plugin because the theme’s validation allows to access the plugin repository and this time, you are being redirected to the plugin repository where all of these bundled plugins were stored.
Hope this explains it briefly.