We've managed to get SSL email going. So much pain...but it works.
One aspect of sending secure email is certificates. We see this happening three ways: 1) embed certificates for a few key services, 2) optionally disabling the certificate validation process, and 3) allowing users to manage their own certificates. The first two are easy, #3 is not hard, but does involve quite a bit of work that we can't get done until at least DmD 2.3. We are currently planning #1 and #2 in DmD 2.2, due out Q1.
So here's my request: We are going to embed support for a handful of mail services. Give us some input into what you'd like us to support. Obvious ones are GMail and Yahoo. We use Office365 here at Host, so that one will show up too. Beyond that, we'd like to hear your input!
Just an FYI: If we don't embed your preferred service, it doesn't mean you won't be able to send email through it, it just means that we won't be able to validate the certificate of that service.