You see the following error during Office 365 to Domino mail flow:
2014-10-14 10:40:03,562 WARN logging [Proxy 1] - Message Number [1] on Thread [9] from Exchange (Office365:37472) to Domino (10.00.00.00:25): Failed to secure the connection from CMN to the Destination Domino server and the SMTP state is unknown. A new connection to the Destination Domino server will be created. TLS will not be used for this connection: IOException: Authentication failed because the remote party has closed the transport stream.
Connection security is set to FORCED and the mail does not flow
WORKAROUND 1
Change connection security from FORCED to OPTIMISTIC in Office 365 if you would NOT like TLS from Office 365 to CMN and CMN to Domino
WORKAROUND 2
Install the certificate in Domino