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Is there a way to use a dedicated Exchange 2013 Send Connector for encrypted messages only?

Elmos Woods
Elmos Woods asked
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We are working with two outbound providers on our on-premise Exchange 2013 environment:  ProofPoint which provides encryption on demand and Mailjet which gives us detailed deliverability stats and reports.  Unfortunately, we're stuck with using one or the other, mainly because Mailjet has authentication requirements that ProofPoint's configuration can't meet.  So, is there a way to configure Exchange so that all messages with the "[ENCRYPT]" in the Subject or Body would go through the ProofPoint connector and anything else through the Mailjet one?  Ideally, if we could find a provider that gives both the reporting AND the encryption-on-demand, that would probably be the optimal option.  Thanks!
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KimputerIT Manager

Commented:
Multiple Send connectors, know which to use based on the outgoing domain of the recipient, no other rules are available.
Elmos WoodsSystems Administrator

Author

Commented:
Thanks, Kimputer, I figured as much; but is there a way to govern, based on certain message criteria, which connector is used after leaving the Outbox?
KimputerIT Manager

Commented:
There's no other way to govern this (in current config).

Insert a Linux machine inside your network topology, with Postfix installed (that will relay to the correct smarthost according to subject)
Elmos WoodsSystems Administrator

Author

Commented:
Thanks again Kimputer, I just saw the part about Postfix.

So, if we were to use something like this solution, would we leave the current Send Connectors in place and would we have to disable them?
IT Manager
Commented:

Have one Send Connector (or more if you wish). The emails you cannot split, you send to Postfix to split.