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Question on Transport Rules - Exchange 2010 SP1

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I have a request from HR to block a certain user from sending email outside of the organization. 

I found directions for setting up the Transport Rule and for testing purposes I created a Distribution group and added myself to it. I have forced replication and waited a little while before testing and I am still able to send email outside of our organization.

Not sure what I am missing. Our email goes to Proofpoint after it leaves out servers but if the Transport Rule is there it shouldn't be even making it to Proofpoint, Right?

I just am not sure what I am doing wrong? 

Any advice?


Jessica Cochran


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