I think you'll need 2 rules.

Try this:

For the first one, use a predicate of emails from inside the organization, 
where the To: header contains off...@domain.com<mailto:off...@domain.com>.

For the second,  use a predicate of emails from inside the organization, where 
the From: header contains ad...@domain.com<mailto:ad...@domain.com>.



From: Liby Philip Mathew [mailto:lmat...@path-solutions.com]
Sent: Thursday, September 23, 2010 1:52 AM
To: MS-Exchange Admin Issues
Subject: Transport rule

Hi,
I have an EDGE server in DMZ and all other role on a single server in the 
internal network.
I need to create a transport rule such that all mails send by the internal user 
to a DG called off...@domain.com<mailto:off...@domain.com> should be NDR'ed 
back to the internal sender with a custom message such as "Please use 
a...@domain.com<mailto:a...@domain.com> instead of 
off...@domain.com<mailto:off...@domain.com>".  But any mail from the external 
sender should be delivered to off...@domain.com<mailto:off...@domain.com>.  And 
mails from internal DG ad...@domain.com<mailto:ad...@domain.com> should also be 
delivered tooff...@domain.com<mailto:off...@domain.com> DG.
I cannot figure out a suitable rule/condition/exception combination.
Appreciate any help
Regards
Liby

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