Jim Murphy wrote:

I have a program that only allows me to enter a From email address and a mail server IP in its setup. Is there any way that I could enter a username and a password in stunnel.conf and let Stunnel send this information out to Office 365 or Gmail for delivery?

Such feature is not supported in stunnel. There is also no way to implement it without a major rewrite of stunnel.

On my TODO list http://www.stunnel.org/?page=sdf_todo required infrastructure is marked as "Protocol support *after* SSL is negotiated".