Hello,

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.

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

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 can provide my config if needed, although I don't really think the
problem is there, given that the iPhone is having no problems sending mails.

Any suggestions would be greatly appreciated.
-- 
Regards,
Nick

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