According to the documentation, SynchronizingLoginModule should always be the final login module as it always succeeds. http://docs.jboss.com/jbportal/v2.6/referenceGuide/html_single/#authentic... With that in mind, the original order of the the login modules were: NtlmLoginModule IdentityLoginModule SynchronizingLoginModule After reading NM-156's solution, I re-ordered it to: IdentityLoginModule NtlmLoginModule SynchronizingLoginModule I also changed the IdentityLoginModule flag attribute from "sufficient" to "optional". to match NM-156's example. And after reading NM-156's last message, i tried NtlmLoginModule SynchronizingLoginModule IdentityLoginModule All of the above produced the same error. View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=4089491#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...