I've downloaded and tried it with JBoss 3.2.8 SP1 and now jaas works with 
java2ClassLoadingCompliance set to false. So both the past two threads I've 
been pushing on this have been in vain. JBoss has fixed the problem. 
anonymous wrote : Given the still heavy use of 3.2.3 it would be nice to be 
able to resolve the original problem though.
Also, this is obviously an unreasonable request since a) it's been fixed in the 
3.2.x stream, and b) they'd have to realease what? 3.2.3 SP1 ? Probably not 
happening.

I think I found the reference to what took care of this issue. In the release 
notes for JBoss 3.2.6RC2 there's a note about jaas:
https://sourceforge.net/docman/display_doc.php?docid=24862&group_id=22866
anonymous wrote : JBossWeb
  | Externalize the JAAS based authentication and authorization realm 
implementation to server.xml and specify the default certificatePrincipal 
attribute. The certificatePrincipal attribute gives the class name of the 
org.jboss.security.auth.certs.CertificatePrincipal impl used for mapping X509[] 
cert chains to a Princpal.
I could be wrong in my reading of this, but if the jaas realm is externalized, 
then it will be able to look up jndi names properly again, and thus will be 
able to access defined login-config's independantly of the web context that's 
it's working for.

In short: I feel silly. Very, very silly.

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