I’ve been testing the Automatic Upgrade Plugin for WordPress the last few weeks. I have used it for the last two WP upgrades 2.6.1 and 2.6.2. So far it has worked flawlessly to provide simple and seamless upgrades. I do follow each step in the process without ever selecting the option to “skip” a step. I should add that I have actually run four upgrades successfully as I am using this plugin on two separate WP installations.
On a third, separate installation, I was not able to successfully run the upgrade. I’m not surprised though as this instance is behind a firewall and running on a Windows server.