As many of you who’ve upgraded to the new WordPress 2.5 version have maybe noticed there is an option on the Plugins page which basically suggests that you can auto-upgrade a plugin. I would strongly suggest you do NOT use this function right now. First off, this is not a feature that is directly supported by plugin authors, it is a function that works outside of the plugin. So if something goes wrong there may be no way for any plugin author to help you fix the situation since the plugin itself did not do the action. Secondly it’s been acknowledged that this feature is really not very robust yet and may very well fail and hose your entire WordPress insall.
I would strongly suggest that you continue to download all plugins yourself and upload them to the server. In the case of AWSOM.org plugins they all upgrade themselves properly when you reactivate them, so it’s actually not really more difficult anyway.