I am having similar problems. Environment: MS Exchange relay JBPM 3.2.1 SQLServer Tomcat required property mail.smtp.auth = true I need to extend org.jbpm.mail.Mail in order to include an Authenticator when getting the Session. I have set two jbpm.cfg.xml properties: - resource.mail.properties - mail.class.name and have included a jbpm.mail.properties file at the root of the classpath My properties file appears to be loading but my custom mail delegation class is not used. anonymous wrote : | org.jbpm.JbpmException: couldn't send email | org.jbpm.mail.Mail.send(Mail.java:150) | org.jbpm.mail.Mail.send(Mail.java:113) | org.jbpm.mail.Mail.execute(Mail.java:63) | org.jbpm.graph.def.Action.execute(Action.java:122) | org.jbpm.graph.def.GraphElement.executeAction(GraphElement.java:255) | org.jbpm.graph.def.GraphElement.executeActions(GraphElement.java:220) | org.jbpm.graph.def.GraphElement.fireAndPropagateEvent(GraphElement.java:190) | org.jbpm.graph.def.GraphElement.fireEvent(GraphElement.java:174) | org.jbpm.graph.def.Node.enter(Node.java:302) | sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) | sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39) | sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25) | java.lang.reflect.Method.invoke(Method.java:597) | ... | and anonymous wrote : | root cause | | javax.mail.AuthenticationFailedException | javax.mail.Service.connect(Service.java:306) | javax.mail.Service.connect(Service.java:156) | javax.mail.Service.connect(Service.java:105) | javax.mail.Transport.send0(Transport.java:168) | javax.mail.Transport.send(Transport.java:98) | org.jbpm.mail.Mail.send(Mail.java:148) | org.jbpm.mail.Mail.send(Mail.java:113) | org.jbpm.mail.Mail.execute(Mail.java:63) | org.jbpm.graph.def.Action.execute(Action.java:122) | org.jbpm.graph.def.GraphElement.executeAction(GraphElement.java:255) | org.jbpm.graph.def.GraphElement.executeActions(GraphElement.java:220) | org.jbpm.graph.def.GraphElement.fireAndPropagateEvent(GraphElement.java:190) | org.jbpm.graph.def.GraphElement.fireEvent(GraphElement.java:174) | org.jbpm.graph.def.Node.enter(Node.java:302) | sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) | sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39) | sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25) | java.lang.reflect.Method.invoke(Method.java:597) | org.hibernate.proxy.pojo.cglib.CGLIBLazyInitializer.invoke(CGLIBLazyInitializer.java:157) | org.jbpm.graph.def.Node$$EnhancerByCGLIB$$affe36f9.enter() | org.jbpm.graph.def.Transition.take(Transition.java:151) | org.jbpm.graph.def.Node.leave(Node.java:393) | org.jbpm.graph.node.StartState.leave(StartState.java:70) | ... | Additional troubleshooting (hacking) . . . I have also modified (println statement) JpdlXmlReader and MailAction and put them ahead of the jar in the class loading order and it appears that they do not get used. View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=4077072#... Reply to the post : http://www.jboss.com/index.html?module=bb&op=posting&mode=reply&a...