Bryan Vyhmeister wrote:
In my situation, all SMTP AUTH is sent through port 465 (smtps) using TLS. I hope that helps.
First, smtps (port 465) is deprecated, so you should use the STARTTLS+submission port (587) unless there is a specific reason to use smtps. The iPhone supports SARTTLS fine.
Next - there is absolutely no evidence that SMTP_AUTH is attempted in your log snippet:
Jul 29 20:10:02 ubuntu postfix/smtpd[28892]: connect from unknown[166.205.142.84] Jul 29 20:10:06 ubuntu postfix/smtpd[28892]: NOQUEUE: reject: RCPT from unknown[166.205.142.84]: 554 5.7.1 xxx@gmail.com: Relay access denied; from=amit@outsidedomain.com to=xxx@gmail.com proto=ESMTP helo=<[10.67.168.110]> Jul 29 20:10:06 ubuntu postfix/smtpd[28892]: disconnect from unknown[166.205.142.84]
Enable the submission port in postfix (just uncomment the example), and tell your iPhone to use SARTTLS on port 587.
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Best regards,
Charles