I'm at a small university where my mac network is sandboxed inside of a greater campus network. The main IT dept doesn't want me to relay mail through them (completely ignorant of macs and worried my network will mess them up) so I'm trying to relay through a gmail account. I have an equipment checkout form on my local network that is supposed to send emails to the users when certain things are approved/etc, but would also like normal server status emails (like warnings when disks are full, etc) to be sent externally.
Anyway, turned on the mail server and have my gmail account set up. Checked "Relay outgoing mail through host: smtp.gmail.com" along with the gmail's account credentials in Server Admin. However, when an email is sent out, my log returns:
Apr 12 15:05:44 myserver postfix/pickup: 6B896EAF8C8: uid=70 from=<_www>
Apr 12 15:05:44 myserver postfix/cleanup: 6B896EAF8C8: message-id=<20120412200544.6B896EAF8C8@myserver.example.com>
Apr 12 15:05:44 myserver postfix/qmgr: 6B896EAF8C8: from=<firstname.lastname@example.org>, size=600, nrcpt=1 (queue active)
Apr 12 15:05:44 myserver postfix/smtp: 6B896EAF8C8: to=<email@example.com>, relay=smtp.gmail.com[18.104.22.168]:25, delay=0.2, delays=0.02/0.02/0.14/0.02, dsn=5.7.0, status=bounced (host smtp.gmail.com[22.214.171.124] said: 530 5.7.0 Must issue a STARTTLS command first. gr1sm30865123igc.1 (in reply to MAIL FROM command))
Apr 12 15:10:44 myserver postfix/smtp: 6B896EAF8C8: conversation with smtp.gmail.com[126.96.36.199] timed out while sending RCPT TO
Apr 12 15:10:44 myserver postfix/cleanup: A1C0EEAF99A: message-id=<20120412201044.A1C0EEAF99A@myserver.example.com>
Apr 12 15:10:44 myserver postfix/bounce: 6B896EAF8C8: sender non-delivery notification: A1C0EEAF99A
Apr 12 15:10:44 myserver postfix/qmgr: A1C0EEAF99A: from=<>, size=2643, nrcpt=1 (queue active)
Apr 12 15:10:44 myserver postfix/qmgr: 6B896EAF8C8: removed
Apr 12 15:10:44 myserver postfix/local: od[getpwnam_ext]: no attribute dsAttrTypeStandard:MailAttribute in record for user _www
Apr 12 15:10:44 myserver postfix/pipe: A1C0EEAF99A: to=<firstname.lastname@example.org>, relay=dovecot, delay=0.04, delays=0.02/0.01/0/0.02, dsn=2.0.0, status=sent (delivered via dovecot service)
Apr 12 15:10:44 myserver postfix/qmgr: A1C0EEAF99A: removed
It appears to not be going through due to the STARTTLS issue. Per another post I found, I added the line "smtpd_tls_security_level = may" to main.cf. I also tried changing "smtpd_use_tls = no" and "smtpd_enforce_tls = no" both to "yes", but the result was always exactly the same.
On a minor side note, how was the "_www" account created and is there any way I can change this?