I know in Active Directory you can forward messages received by a specific person to another person or outside email address. Is there a way to also forward every email sent by a specific person to another mailbox?
You should be able to set up archiving for that user as well. We use Ironmail, so I'm able to quickly audit any individual user, but not sure how it can be done in a pure Exchange environment.
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Create a new username and mailbox, call it something like Archiving, and then create a new mailbox store on your Exchange Server. Move the users you wish to monitor into that store, right-click on the store and select Properties, and then put a tick in the "Archive all messages sent or received by mailboxes on this store" box. Then click on the "Browse" button and select the Archiving user.
Now, any mail sent or received by the mailboxes in the new store, will automatically be copied to the Archiving mailbox. Simply log into it via outlook or OWA, and view all mails sent, or received. If you wish to forward the messages to an external user, just change the properties of the Archiving user, to the external address.