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Why wouldn't he simply converge all of those mailboxes into a single one? After all, isn't efficiency one of the key considerations? Why would you have several mailboxes for a single user on an exchange server anyway?

With a little rational thinking, he could solve both problems by giving them a single mailbox, with separate addresses receiving and sorted by rule in Exchange. Only one outgoing though, which isn't a bad thing, unless he is masquerading as different people, which is just strange.