Hi,

yes. Sorry for the late reply. I haven't tested another mail client.

I guess it's #opensmtpd @ freenode right?

Thanks,
Eric


> On 2015-07-14, at 15:13, Gilles Chehade <[email protected]> wrote:
> 
> Are you around ?
> 
> Can we arrange for you to come on IRC at a time where I'm around so we
> can do a test on my own MX ?
> 
> 
> On Sat, Jul 11, 2015 at 10:26:17PM +0200, Eric Ripa wrote:
>> Thanks for the response. I suspected that but given that the actual content 
>> in this case is confidential I was a bit hesitant. 
>> 
>> Heres the leading part of the [MSG] section. Can you see anything triggering 
>> this?
>> 
>> 
>> <<< [MSG] From: My Name <[email protected]>
>> <<< [MSG] Content-Type: multipart/signed; 
>> boundary="Apple-Mail=_72DA7FD1-7F93-4028-B624-1213C11481BD"; 
>> protocol="application/pkcs7-signature"; micalg=sha1
>> <<< [MSG] Message-Id: <[email protected]>
>> <<< [MSG] Mime-Version: 1.0 (Mac OS X Mail 9.0 \(3067\))
>> <<< [MSG] Subject: =?utf-8?Q?Re=3A_M=C3=B6tet_imorgon?=
>> <<< [MSG] Date: Sat, 11 Jul 2015 22:16:19 +0200
>> <<< [MSG] References: 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <[email protected]> 
>> <CAA-Q+[REDACTED][email protected]> 
>> <CAA-Q+[REDACTED][email protected]>
>> <<< [MSG] To: [email protected]
>> <<< [MSG] In-Reply-To: <CAA-Q+[REDACTED][email protected]>
>> <<< [MSG] X-Mailer: Apple Mail (2.3067)
>> <<< [MSG] 
>> <<< [MSG] 
>> <<< [MSG] --Apple-Mail=_72DA7FD1-7F93-4028-B624-1213C11481BD
>> <<< [MSG] Content-Type: multipart/alternative;
>> <<< [MSG]   boundary="Apple-Mail=_1D1CF9DB-435D-4B6D-B041-4150C3143099"
>> <<< [MSG] 
>> <<< [MSG] 
>> <<< [MSG] --Apple-Mail=_1D1CF9DB-435D-4B6D-B041-4150C3143099
>> <<< [MSG] Content-Transfer-Encoding: quoted-printable
>> <<< [MSG] Content-Type: text/plain;
>> <<< [MSG]   charset=utf-8
>> <<< [MSG] 
>> .....
>> ..... actual content
>> .....
>> <<< [MSG] --Apple-Mail=_72DA7FD1-7F93-4028-B624-1213C11481BD--
>> <<< [EOM]
>> 
>> 
>>> On 2015-07-11, at 14:34, Gilles Chehade <[email protected]> wrote:
>>> 
>>> On Sat, Jul 11, 2015 at 01:28:29PM +0200, Eric Ripa wrote:
>>>> Hi,
>>>> 
>>>> I occasionally have an issue with outgoing mails not being accepted by 
>>>> OpenSMTPD due to "Message is not RFC 2822 compliant". It's also a 
>>>> recurring problem of a client of mine were I've setup OpenSMTPD. Both 
>>>> systems are running 5.7.1, one on OpenBSD 5.6 and this one on OpenBSD 
>>>> 5.8-beta (snapshot from 2015-07-10).
>>>> 
>>>> I believe this message in the log is a bit strange: received invalid 
>>>> command: "DATA"
>>>> 
>>>> In this particular case the mail is a fairly long conversation with 10+ 
>>>> replies in HTML. In the past the only remedy has been to remove large 
>>>> parts of the email history. I've also seen this occur in a single reply-to 
>>>> instance.
>>>> 
>>>> In all cases so far the MUA has been various versions of Apple Mail, 
>>>> ranging from default version in 10.9 to this example with latest 10.11 
>>>> beta.
>>>> 
>>>> Any way to debug this behaviour it further?
>>>> 
>>>> Thanks
>>>> Eric Ripa
>>>> 
>>>> 
>>>> smtp: 0x147357517000: connected to listener 0x147414db5000 
>>>> [hostname=mail.domain.com, port=587, tag=]
>>>> smtp: 0x147357517000: STATE_NEW -> STATE_CONNECTED
>>>> smtp-in: session 8917f8161d62f58a: connection from host client.isp.com 
>>>> [1.2.3.4] established
>>>> smtp: 0x147357517000: >>> 220 mail.domain.com ESMTP OpenSMTPD
>>>> smtp: 0x147357517000: <<< EHLO [192.168.1.2]
>>>> smtp: 0x147357517000: STATE_CONNECTED -> STATE_HELO
>>>> smtp: 0x147357517000: >>> 250-mail.domain.com Hello [192.168.1.2] 
>>>> [1.2.3.4], pleased to meet you
>>>> smtp: 0x147357517000: >>> 250-8BITMIME
>>>> smtp: 0x147357517000: >>> 250-ENHANCEDSTATUSCODES
>>>> smtp: 0x147357517000: >>> 250-SIZE 36700160
>>>> smtp: 0x147357517000: >>> 250-DSN
>>>> smtp: 0x147357517000: >>> 250-STARTTLS
>>>> smtp: 0x147357517000: >>> 250 HELP
>>>> smtp: 0x147357517000: <<< STARTTLS
>>>> smtp: 0x147357517000: >>> 220 2.0.0: Ready to start TLS
>>>> smtp: 0x147357517000: STATE_HELO -> STATE_TLS
>>>> smtp-in: session 8917f8161d62f58a: TLS started version=TLSv1/SSLv3 (), 
>>>> cipher=ECDHE-RSA-AES256-SHA, bits=256
>>>> smtp: 0x147357517000: STATE_TLS -> STATE_HELO
>>>> smtp: 0x147357517000: <<< EHLO [192.168.1.2]
>>>> smtp: 0x147357517000: STATE_HELO -> STATE_HELO
>>>> smtp: 0x147357517000: >>> 250-mail.domain.com Hello [192.168.1.2] 
>>>> [1.2.3.4], pleased to meet you
>>>> smtp: 0x147357517000: >>> 250-8BITMIME
>>>> smtp: 0x147357517000: >>> 250-ENHANCEDSTATUSCODES
>>>> smtp: 0x147357517000: >>> 250-SIZE 36700160
>>>> smtp: 0x147357517000: >>> 250-DSN
>>>> smtp: 0x147357517000: >>> 250-AUTH PLAIN LOGIN
>>>> smtp: 0x147357517000: >>> 250 HELP
>>>> smtp: 0x147357517000: <<< AUTH PLAIN 
>>>> ZXJpY0dkfoskdofKOKFODSfkODKfoSDkfodskfOSDFZmVZcSxrLHBMeGE5OVFSeUFuSFVDWF1KQg==
>>>> smtp: 0x147357517000: STATE_HELO -> STATE_AUTH_INIT
>>>> smtp-in: session 8917f8161d62f58a: authentication successful for user 
>>>> [email protected]
>>>> smtp: 0x147357517000: >>> 235 2.0.0: Authentication succeeded
>>>> smtp: 0x147357517000: STATE_AUTH_INIT -> STATE_HELO
>>>> smtp: 0x147357517000: <<< MAIL FROM:<[email protected]>
>>>> smtp: 0x147357517000: >>> 250 2.0.0: Ok
>>>> smtp: 0x147357517000: <<< RCPT TO:<[email protected]>
>>>> smtp: 0x147357517000: >>> 250 2.1.5 Destination address valid: Recipient 
>>>> ok                                                                
>>>> [1101/1838]
>>>> smtp: 0x147357517000: <<< RCPT TO:<[email protected]>
>>>> smtp: 0x147357517000: >>> 250 2.1.5 Destination address valid: Recipient ok
>>>> smtp: 0x147357517000: <<< DATA
>>>> smtp: 0x147357517000: STATE_HELO -> STATE_BODY
>>>> smtp: 0x147357517000: >>> 354 Enter mail, end with "." on a line by itself
>>>> 
>>>> ...lots of <<< [MSG]...
>>>> 
>>> 
>>> Problem lies precisely in the [MSG] you have obfuscated ;-)
>>> 
>>> I'm fairly confident that your mail does not have headers + body
>>> 
>>> 
>>>> smtp: 0x147357517000: >>> 550 5.7.1 Delivery not authorized, message 
>>>> refused: Message is not RFC 2822 compliant
>>>> smtp-in: session 8917f8161d62f58a: received invalid command: "DATA"
>>>> smtp: 0x147357517000: STATE_BODY -> STATE_HELO
>>>> smtp: 0x147357517000: <<< QUIT
>>>> smtp: 0x147357517000: >>> 221 2.0.0: Bye
>>>> smtp: 0x147357517000: STATE_HELO -> STATE_QUIT
>>>> smtp-in: session 8917f8161d62f58a: connection from host client.isp.com 
>>>> [1.2.3.4] closed (client sent QUIT)
>>>> 
>>> 
>>> 
>>> -- 
>>> Gilles Chehade
>>> 
>>> https://www.poolp.org                                          @poolpOrg
>>> 
>>> -- 
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>> 
>> 
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> 
> -- 
> Gilles Chehade
> 
> https://www.poolp.org                                          @poolpOrg
> 
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