For the sake of completeness I'll just send a short update to this thread.
We debugged the behaviour using Gilles debug instance and it looks like Apple Mail is generating a single-line References header that doesn't comply to RFC 2822, making it too large in some cases. It should not be >78 characters, if it is it should be split into multiple lines. OpenSMTPD will refuse after >998. In my example the line was 1078 characters. I've filed a bug report with Apple (developer portal), id 21813193 if anyone wants to reference it or something. As a workaround one can use forward instead of reply and copy the recipients from the original thread. Then Apple Mail will simply drop the References header. Thanks a lot to Gilles for the quick debug Eric > On 2015-07-14, at 15:19, Eric Ripa <[email protected]> wrote: > > 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 >>>> >>>> -- >>>> You received this mail because you are subscribed to [email protected] >>>> To unsubscribe, send a mail to: [email protected] >>> >>> >>> -- >>> You received this mail because you are subscribed to [email protected] >>> To unsubscribe, send a mail to: [email protected] >>> >> >> -- >> Gilles Chehade >> >> https://www.poolp.org @poolpOrg >> >> -- >> You received this mail because you are subscribed to [email protected] >> To unsubscribe, send a mail to: [email protected] > > > -- > You received this mail because you are subscribed to [email protected] > To unsubscribe, send a mail to: [email protected] -- You received this mail because you are subscribed to [email protected] To unsubscribe, send a mail to: [email protected]
