> 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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