Thanks for the tip. I could seem to get CascadeType.DELETE_ORPHAN to work in 4.04ga with a Set (didnt try with a List). I saw a bug related to this, http://opensource.atlassian.com/projects/hibernate/browse/EJB-53 but it appears fixed long ago. I made a little test case that persists the Order with one OrderItem. I then call order.getOrderItems().clear() and then call (thru the sessionbean) em.merge(order) and even do an explicit flush(). The underlying row for the OrderItem is not deleted. This whole thing is not a big deal since I can explicitly delete the child objects no longer in the Set. I was just curious as to how to do it automatically. View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=3970615#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...