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Require TLS Send Connectors Through Smart Host?

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Our new Exchange 2013 Server will not be directly connected to the Internet.  It will first forward to a spam filtering appliance on our internal network and then to another non-Exchange SMTP server at the edge of our network.

I don't see how a special Send Connector configured on Exchange to require TLS would work when it doesn't have direct access to send mail outside.  We have to point the send connectors to the smart host anyway since that is the only path out of the network.

What is the best way to configure mandatory TLS to specific domains when Exchange has to relay through other servers?


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