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.

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