After doing some extra digging this is what I found out. 
JBossSecurityMgrRealm created a roleMap keyed by principal(SimplePrincipal) .  
When user only get authenticated bu JBoss, request does not contain principle 
therefore authenticate method is called in JBossSecurityMgrRealm. Here 
SimplePrincipal object is created by the passed in user name and then roles 
lookup by this key.

BUT!!! If user get initially authenticated by the web server(apache) then 
CayoteInvoker that handles request for tomcat sees that user exist in request 
then creates a CayotePrincipal with in a request. Now the authenticate of 
JBossSecurityMgrRealm  is NOT called. Role look up fails because roles are 
keyed by SimplePrincipal and look up is done with CayotePrincipal object.

I hope what I said makes sense to everyone. But this is causing a problem for 
us. I am sure someone else ran into this before. How do we get around it?

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