Here's my latest log message (the dreaded Gmail StartTLS message):
Mar 25 16:46:50 mail2 postfix/smtp: 1E7B4201E0: to=<firstname.lastname@example.org>, relay=smtp.gmail.com[22.214.171.124]:587, delay=0.62, delays=0.02/0.01/0.46/0.13, dsn=5.7.0, status=bounced (host smtp.gmail.com[126.96.36.199] said: 530 5.7.0 Must issue a STARTTLS command first. d4sm414560fga.25 (in reply to MAIL FROM command))
I've tried every combination of relay commands. Gmail definitely seems to like smtp:[smtp.gmail.com]:587 (with or without MX lookups). I don't know if the current iRedmail vanilla configuration likes port 587. I can telnet to the iRedMail mail server and STARTTLS is there when I EHLO mail2.gogridworkz.com. I even type: STARTTLS and I get the TLS ready prompt no problem.
I can connect from an email client like Thunderbird and use TLS on port 587 - again, no problem. Somehow we need to send down my SMTP-AUTH credentials to the Gmail servers from within iRedmail.
BTW: smtp.gmail.com is really a CNAME record that goes to: ASPMX.L.GOOGLE.COM if that is any help. Could it be a Certificate issue?
Anyway, I'm heading out now and I'll catch up with you guys tomorrow.