Just a guess, but it sounds like the behaviour you are seeing is a result of 
the user credentials being cached by JAAS (the login module will therefore not 
revisit the database to check for new roles until the cache has expired).

Fore more info, and how you can manually flush the cache after adding a new 
role to the DB, check out:

http://wiki.jboss.org/wiki/Wiki.jsp?page=CachingLoginCredentials



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