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 <x...@gmail.com>: Relay access
> denied; from=<a...@outsidedomain.com> to=<x...@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.

-- 

Best regards,

Charles

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