It will work if you make:

  | 
  | first=Administrators,Admin,Authenticated
  | second=Users,User,Authenitcated
  | 

"Authenticated" is the role used to secure portal servlet. look into 
jboss-portal.sar\portal-server.war\WEB-INF\web.xml

Yes, with such configuration you need to synchronize user accounts into portal 
database if you want to enable them personalization inside of portal. This is 
going to be better supported in JBP 2.6. For 2.6 we also introduced something 
called SynchronizingLoginModule that can be placed after any other LoginModule 
in authentication chain. When user is authenticated sucessfully it will be 
synchronized into portal DB. There is also version integrated with 
LdapLoginModule. It shouldn be trival to port it for 2.4. 

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