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Disconnecting OutBound Message Session

I would like to know the correct way to logout/disconnect from a session that I attach to from an outbound message using the logged in user's session id. If I catch an exception repeatedly, I eventually get an out of memory error in the TomCat 5 Server that is running my web service.
Do I need to explicitly logout and/or disconnect from my session to release memory on a normal or an abnormal exit from my process ?.
Also, if if anyone can point me to detailed documentation on the Dead Letter queue feature I would appreciate it. We are tying to decide on the best strategy for notifying the user of the success/failure of the outbound message delivery and processing. Should we let exceptions roll back to SalesForce, or try to handle them ourselves ?.