I have a Java program that connects to a webserver using SSL/TLS, and sends various HTTP requests over that connection. The server is localhost and is using a self-signed ce
The stack trace is from you client code and your client 'Received [a] fatal alert'. In other words, the SSL error happened in Jboss, not your client.
Your client side custom TrustManagers have therefore nothing to do with it. My wild guess is that your new Jboss 7 is configured to require client certificate and your client did not present any.
To debug your SSL connection, use openssl and try this:
openssl s_client -connect jboss.server.com:443
or is it is an SSLV3 server
openssl s_client -connect jboss.server.com:443 -ssl3
This should print a lot of interesting information.