Cheers cgriffith, Well I have a custom login module (same) on both the tomcat side (common/lib) and the jboss side (lib). Tomcat points to the login conf file through the java option -Djava.security.auth.login.config and to jboss application server -Djava.naming.provider.url. On the tomcat login conf I have the org.jboss.security.ClientLoginModule required so to chain the authentication to jboss with the option of multi-threaded = "true and password-stacking = "useFirstPass". As I said before if multi-threaded is set to false it works perfectly, set to true it works intermittently.
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