I got it working, the problem ended up being the sql i was using for the roles Query. My database (the jboss portal) db. Doesn't have a schema that directly matches the way the query has to be shaped. By looking at the source of DatabaseServerLoginModule.java I was able to figure out what it was looking for in each query. The fix was to make a view that did the joining needed to create the schema that jaas wants. My docs / config were right. And in the end you do have to move login-config.xml out of your web.xml and into /deploy/conf/login-config.xml for the server to see it. This is on bundled AS 4.0.4 and portal 2.4. Thanks to everyone for thier help. View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=3985633#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...