Our resolution was to move the smtp service to the 2003 server and move all of the mailboxes, too. Just eliminating the 5.5 server completely is a good way to elimninate a lot of problems.
We have a mixed Exchange 5.5/2003 system and are experiencing the same issue. The Exchange 5.5 server is the server responsible for outbound smtp delivery. It appears that the 5.5 IMS uses the x.500 address to create the reply address from an Exchange 2003 user.
Testing the "real" smtp...
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