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I have some users that I do not want to mail outside of my company. In the EMC i go to Organization config>hub transport>transport rules. In there I made a rule that limits certain people in a distribution list to not being able to email outside.

The text of the rule is as follows:

Apply rule to message
From a member of 'internal_emails@blahblah.com' (this is the distribution group)
and sent to users that are 'outside the organization'
Send 'this account is not authorized to send external emails' to sender with '5.7.1'

The rule works fine but here is the issue: The user (auditor) that is sending the email is sending it to another group called reports. On this group is the quality supervisor (she is not in the group that limits her to internal only) and she travels sometimes for training. When she does she like me to forward her company email to a gmail account she can access on her cell phone. So when i turn forwarding on for her, the auditor gets a bounce message and the email seems to go poof. It does not make it to her outlook inbox or the gmail one.

This issue only pops up when someone on the internal_emails list tries to email someone with an external forwarder.

Is there a way that I can make it to where these people can not email out unless they are emailing a forwarder?

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Ever thought of having her use OWA or give her a proper smartphone? ActiveSync is really nice. –  TomTom Jun 20 '11 at 17:22
    
She is using OWA. She does not travel but a few times a year and the owners don't give phones out very often. And yes, ActiveSync rocks =) –  Grumsy Jun 20 '11 at 18:46
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2 Answers

The "good" solution: Give her access to company email on the cell phone.

The "bad" solution: Have her forward the email via a mailbox rule instead of having you change it on the exchange recipient - this would generate a second outbound message instead of letting exchange resolve straight to the external address when expanding the distribution group, blocking the message.

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Her phone does not support exchange (I have tried). All I have changed is added an external email address as a forwarder. Seems to me that if you forward to her mail box it should then forward to her external, but that isn't the case. In fact the message seems to go no where. Bounce message at the user, and then nothing in either mail box for the recipient. That is the part that has me stumped. –  Grumsy Jun 20 '11 at 18:02
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What's the exact predicate you're using for the rule?

If my limited understanding of Exchange is correct, you should be able to specify a compound predicate, with an exception.

i think the exact parameter is ExceptIfSentTo

this way, it will allow emails through, if it is being sent to her gmail.

edit: source is http://technet.microsoft.com/en-us/library/bb125138.aspx (ctrl+f Exemptifsentto to jump straight there)

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