Thanks Michal.
Reio Remma has also replied to me, pointing me in the right direction.

It turns out that when you enter username and password for the SMTP server
in Apple Mail using automatic connection settings (snap1), it only checks
the connection to that server (never tries to authenticate), hence it marks
it green and good to go.
[image: snap1.png]

I had to further manually specify the authentication method to be password
and connection to be via TLS/SSL (snap2) for it to actually start doing it.
[image: snap2.png]
Thanks guys for the help.

On Tue, Apr 10, 2018 at 3:56 PM Michal Krzysztofowicz <m...@frozen-geek.net>
wrote:

> > On 9 Apr 2018, at 23:12, Nick Gyurov <ngyu...@gmail.com> wrote:
> >
> > Hello,
>
> Hi,
>
> >
> > Running OpenSMTPD 6.0.0 on OpenBSD 6.2.
> >
> > I'm having a weird problem being unable to send mail with Apple Mail on
> macOS, while I'm perfectly able to send mails using the same configuration
> from the native mail client on an iPhone.
>
> I’m using the same configuration and have no issue with neither the Apple
> Mail nor with the iOS client.
>
> > The error message from Apple Mail is:
> > The server response was: Invalid recipient
> >
> > This is what I have in maillog on an attempt to send a mail using Apple
> Mail:
> > Apr  9 20:28:52 dovecot: imap-login: Login: user=<foobar>, method=PLAIN,
> rip=x.x.x.x, lip=y.y.y.y, mpid=18368, TLS, session=<7esJQXBpXdh2vbEC>
> > Apr  9 20:29:09 smtpd[52562]: e012cc5a233196ef smtp event=connected
> address=x.x.x.x host=host.name
> > Apr  9 20:29:09 smtpd[52562]: e012cc5a233196ef smtp event=starttls
> address=x.x.x.x host=host.name ciphers="version=TLSv1.2,
> cipher=ECDHE-RSA-AES256-GCM-SHA384, bits=256"
> > Apr  9 20:29:11 smtpd[52562]: e012cc5a233196ef smtp event=failed-command
> address=x.x.x.x host=host.name command="RCPT TO:<foo...@gmail.com>"
> result="550 Invalid recipient"
> > Apr  9 20:29:11 smtpd[52562]: e012cc5a233196ef smtp event=closed
> address=x.x.x.x host=host.name reason=quit
> >
> > The same attempt a minute before from iOS:
> > Apr  9 20:27:49 smtpd[52562]: e012cc563f523806 smtp event=connected
> address=x.x.x.x host=host.name
> > Apr  9 20:27:49 smtpd[52562]: e012cc563f523806 smtp event=starttls
> address=x.x.x.x host=host.name ciphers="version=TLSv1.2,
> cipher=ECDHE-RSA-AES256-GCM-SHA384, bits=256"
> > Apr  9 20:27:50 smtpd[52562]: e012cc563f523806 smtp event=authentication
> user=foobar address=x.x.x.x host=host.name result=ok
> > Apr  9 20:27:52 smtpd[52562]: e012cc563f523806 smtp event=message
> address=x.x.x.x host=host.name msgid=dd47731d from=<foo...@domain.com>
> to=<foo...@gmail.com> size=556 ndest=1 proto=ESMTP
> > Apr  9 20:27:52 smtpd[52562]: e012cc5944757c28 mta event=connecting
> address=smtp+tls://108.177.126.26:25 host=108.177.126.26
> > Apr  9 20:27:52 smtpd[52562]: e012cc5944757c28 mta event=connected
> > Apr  9 20:27:53 smtpd[52562]: e012cc5944757c28 mta event=starttls
> ciphers=version=TLSv1.2, cipher=ECDHE-RSA-CHACHA20-POLY1305, bits=256
> > Apr  9 20:27:53 smtpd[52562]: smtp-out: Server certificate verification
> succeeded on session e012cc5944757c28
> > Apr  9 20:27:54 smtpd[52562]: e012cc5944757c28 mta event=delivery
> evpid=dd47731d6e0f2b5c from=<foo...@domain.com> to=<foo...@gmail.com>
> rcpt=<-> source="y.y.y.y" relay="108.177.126.26 (108.177.126.26)" delay=3s
> result="Ok" stat="250 2.0.0 OK 1523305674 w39si1129555edw.282 - gsmtp"
> > Apr  9 20:28:04 smtpd[52562]: e012cc5944757c28 mta event=closed
> reason=quit messages=1
>
> It seems like the Apple Mail is not trying to authenticate for outgoing
> SMTP connection (the third line in your log is the failed-command event).
> The authentication does seem to be set up and working correctly for the iOS
> client. This may or may not be an issue, but certainly is a difference
> between the two.
>
> >
> > Looking at RFC 5321, "RCPT TO:<forward-path>" seems to be a valid syntax
> but for some reason Apple Mail is still getting a 550 reply.
>
> I *think* this may be just a behaviour of OpenSMTPD when authentication is
> required however the user didn’t attempt authentication before trying to
> send the mail.
>
> I would check the Apple Mail configuration to see if authentication is set
> there.
>
> Regards,
> mike
>
> --
> Michal Krzysztofowicz
> http://beautifulocean.org/
> --
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> --
Regards,
Nick

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