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Very well, if this doesn't work, then you need to verify that logging is enabled on the SMTP service of the 2003 server, then verify that Message tracking is enabled for that Exchange Server, under it's properties in ESM. Send a message, check the queue and then examine the smtp logs for errors...

Not sure why you posted this here, and I've never seen anyone run 5.5 and 2000 at the same time, but if configure a SMTP connector on the 2003 server for your outgoing mail it should resolve your problem. If all mail has to route through the 5.5 server then configure the new connector to use the...