from the RFC:
"Receiving implementations would do well to handle an arbitrarily large number
of characters in a line for robustness sake.”
Apple Mail is wrong according to the RFC, and that is something Apple should be
dealing with. But is there a reason why OpenSMTPD is enforcing this arbitrary
boundary intended to increase compatibility?
ED.
> On 2015, Jul 14, at 10:04 AM, Eric Ripa <[email protected]> wrote:
>
> 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]
>>>>
>>>>
>>>> --
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>>>> To unsubscribe, send a mail to: [email protected]
>>>>
>>>
>>> --
>>> Gilles Chehade
>>>
>>> https://www.poolp.org @poolpOrg
>>>
>>> --
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>>
>>
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