I have a situation where management has requested a user be setup with a 
mailbox that is prohibited from sending or receiving mail outside of our 
company. I’ve created two different transport rules as follows. Environment: 
Exchange 2007 SP1 RU7

Block Receiving External
Apply rule to messages
from users Outside the organization
   and sent to <useraddress>
send Delivery not authorized, message refused to sender with 5.7.1

Block Sending External
Apply rule to messages
from <useraddress>
   and sent to users Outside the organization
send Delivery not authorized, message refused to sender with 5.7.1

This setup works great except for when our Help Desk tracking system sends 
automated messages based on ticket creation, updates, and closures. Even though 
the tracking system is “inside” the organization, and the emails always appear 
to be coming from *...@ourdomain.com, the automated messages are being bounced 
back. I know that I need to use the exceptions portion of the rule to try to 
allow these through but am hitting a wall. The tricky part to this is that the 
From, Subject, and Body fields are never consistent so many of the exceptions 
in the rules are not working. Thoughts? Suggestions? Can I create an exception 
based off IP address of the Help Desk server? If so, how to I add that to my 
transport rules?

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