I've been set the challenge of configuring transport rules such that emails with a sensitive information type are always send securely, either with TLS or with a fall-back Office Message Encryption. This should be automatically handled without a NDR message going to the sender or the sender having to choose OME when sending.
I've stumped on how to detect TLS wasn't negotiated and taking alternative action
The logic I need is like -
IF (Email contains sensitive information type="Personal") THEN
// must be sent secured
TRY send on Connector with Mandatory TLS
CATCH // TLS failed
encrypt message with Office Message Encryption
send on connector with Speculative TLS
ELSE
// general content can go speculative
send on connector with Speculative TLS
END IF
