SBS 2011 Essentials SMTP relay to Office 365 for inhouse application
I has a SBS 2011 Essentials network that is using Office 365 for Exchange. They have an inhouse application that needs to forward email reports to one of the Office 365 mailboxes. Connection to Office 365 requires TLS and unfortunately the application does not support TLS. I believe I can configure IIS on the SBS 2011 Essentials server to accept a non-encrypted connection from the client and then forward to Office 365 using a send connector configured with TLS. Has anybody done that?