Actually there were two issues. 1) The issue described above where deployments were undeployed in random order so the conf/jboss-service.xml classloader which includes jndi.properties was removed too early. 2) The undeploy was using the NoAnnotationURLClassLoader of bootstrap-beans.xml as the context classloader which wouldn't be able to see that classloader anyway. I've fixed (1) http://jira.jboss.com/jira/browse/JBAS-5175 I've hacked around (2), but the proper fix will have to wait for the update to the MC that does the proper context classloader setting http://jira.jboss.com/jira/browse/JBAS-5176 View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=4123642#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...