As mentioned by WP Engineer, WordPress 2.9 recently had a new feature added to it called bulk plugin upgrades. The interesting thing about this feature is back on September 11th, Matt published this through his Twitter feed:
Just upgraded three plugins in about 30 seconds using one-click upgrade — wish you could do them all at once though.
Well, now you can. I attended the WordPress developers chat today and according to the devs, the bulk upgrader works, all it needs now is to be tied into the API along with some cosmetics. I’m sure there are plenty of you, including myself that is pleased to see this addition to WordPress. However, I wonder what happens if during a bulk upgrade, one of the plugins fails. Does the upgrader skip the plugin and move on to the next one or does it ruin the entire upgrade? Looking forward to the answer in the comments.