After much gnashing of teeth and wailing, we’ve finally found a web framework for Java that looks usable. Stripes looks simple enough to be usable without requiring insane amounts of configuration. It also uses Java 5 features like annotations and generics to great effect. Plus, minimal configuration files. I strongly recommend checking out the Quick Start.
It’s not rails (by a long shot), but seeing as how we are forced to use Java at work, it seems to be one of the least unpleasant options so far.