I’m near done configuring my mail server. Last night I got sendmail configured to use STARTTLS, and to require it for SMTP AUTH. I now don’t allow cleartext passwords, so I can feel safe using my iPhone to send mail through my server when I’m not at home. Not enforcing STARTTLS wasn’t a big deal for my desktop since it’s on a secure wired LAN with my mail server, but there are times when I want to use my iPhone and laptop to send mail when I’m away from home, and hence I need to enforce crypto for SMTP AUTH.
All works fine using Mail on my hackintosh, Mail on my MacBook Pro, Outlook on my hackintosh, and of course my iPhone. I need to write up everything I did so I can repeat it in the future if necessary.