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Exchange 2010 Routing

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Problem routing mail;

I have an internal user with a secure email account. This account routes externally to a smart host via a separate send connector.  The problem I'm seeing is if the user sends email via their secure account to another user who is internal the recipient never receives the message and also if the same user sends to another secure email account in the same organisation they never receive the message either. When the message is sent to an external source the message is sent with no problem.

In message tracking I can see that the message goes external even though the user is internal and the address is accepted in Exchange.  The message seems to be looping but never delivered.

Any advice please...


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