One solution to my problem is to find out the UserPermissions to be deleted and remove them manually using the entity manager's remove method. I think it's a bit strange that this cannot be done by the container. After all it is able to store new relationships in the DB and update existing ones. So it should be able to remove existing ones as well. Anyways, things work the way I described, albeit my code looks all cluttered now. :-/ Regards, Thomas View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=4171067#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...