Re: [ietf-smtp] [Proposal] confusing parts of the mail system, was 250-MARKDOWN

Ned Freed <ned.freed@mrochek.com> Thu, 17 January 2019 13:41 UTC

Return-Path: <ned.freed@mrochek.com>
X-Original-To: ietf-smtp@ietfa.amsl.com
Delivered-To: ietf-smtp@ietfa.amsl.com
Received: from localhost (localhost [127.0.0.1]) by ietfa.amsl.com (Postfix) with ESMTP id EDB75128B14 for <ietf-smtp@ietfa.amsl.com>; Thu, 17 Jan 2019 05:41:25 -0800 (PST)
X-Virus-Scanned: amavisd-new at amsl.com
X-Spam-Flag: NO
X-Spam-Score: -2.001
X-Spam-Level:
X-Spam-Status: No, score=-2.001 tagged_above=-999 required=5 tests=[BAYES_00=-1.9, DKIM_SIGNED=0.1, DKIM_VALID=-0.1, DKIM_VALID_AU=-0.1, SPF_PASS=-0.001] autolearn=unavailable autolearn_force=no
Authentication-Results: ietfa.amsl.com (amavisd-new); dkim=pass (1024-bit key) header.d=mrochek.com
Received: from mail.ietf.org ([4.31.198.44]) by localhost (ietfa.amsl.com [127.0.0.1]) (amavisd-new, port 10024) with ESMTP id r89NkBOviLl9 for <ietf-smtp@ietfa.amsl.com>; Thu, 17 Jan 2019 05:41:24 -0800 (PST)
Received: from mauve.mrochek.com (mauve.mrochek.com [66.218.59.24]) (using TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)) (No client certificate requested) by ietfa.amsl.com (Postfix) with ESMTPS id 3723812426E for <ietf-smtp@ietf.org>; Thu, 17 Jan 2019 05:41:24 -0800 (PST)
Received: from dkim-sign.mauve.mrochek.com by mauve.mrochek.com (PMDF V6.1-1 #35243) id <01R23VQGS3NK00GED8@mauve.mrochek.com> for ietf-smtp@ietf.org; Thu, 17 Jan 2019 05:36:21 -0800 (PST)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=mrochek.com; s=201712; t=1547732180; bh=LP/3vjmhWxhVW0VuZHV3RzzdMR0SJJMFxxdU3sxqwFo=; h=Cc:Date:From:Subject:In-reply-to:References:To:From; b=iehtC+xQcarSlpu8Sz6mHbt07n3LJ2CrTwSOgr+EcyweUawBgg443wptOHq0PzcNs Dd2m2TL1q9fYRgxEd6/szvRAjy28BMkAw30DnjEsxqKStoX2H5ST0TKfCPHGh4BZCq ejWYojMdvO0Pdnisgg31Lkgj62T1Q8f9zVnkohWI=
MIME-version: 1.0
Content-transfer-encoding: 7bit
Content-type: TEXT/PLAIN; CHARSET="US-ASCII"
Received: from mauve.mrochek.com by mauve.mrochek.com (PMDF V6.1-1 #35243) id <01R1N39ADWKW00004L@mauve.mrochek.com>; Thu, 17 Jan 2019 05:36:16 -0800 (PST)
Cc: Ned Freed <ned.freed@mrochek.com>, John Bucy <jbucy=40google.com@dmarc.ietf.org>, ietf-smtp <ietf-smtp@ietf.org>
Message-id: <01R23VQEHUIQ00004L@mauve.mrochek.com>
Date: Thu, 17 Jan 2019 05:28:11 -0800
From: Ned Freed <ned.freed@mrochek.com>
In-reply-to: "Your message dated Thu, 17 Jan 2019 04:55:05 -0800" <64374ebd-6a07-4463-7d3d-a232bd1a475a@digilicious.com>
References: <CAOEezJTxTN9x_JFXgLidj9k8NVgFTRyqyQc4Aak8UEQuvjiM0w@mail.gmail.com> <20190109143529.33122200C76CAD@ary.local> <460d4589-5517-3762-5764-7474523dd09b@digilicious.com> <01R1U95VCAHI00004L@mauve.mrochek.com> <74e22977-8ee8-c762-4882-b56e5911430e@digilicious.com> <CALui8C2qzp_jBo=YHA+XXBGF6+jigDeEaX24L2bohQBdaXKHwg@mail.gmail.com> <2ea48fe6-eb48-02e1-d3e2-53782f3ff758@digilicious.com> <alpine.OSX.2.21.1901111607320.22582@ary.qy> <bcf3958d-cd42-fc3c-57fc-56a5f8394b37@digilicious.com> <alpine.OSX.2.21.1901111647330.22750@ary.qy> <5b6ddc8f-9c53-df04-0f61-721fad0972f3@digilicious.com> <CALui8C3934HTxrY-JGB3rAu1dX1z8oz1AK8jmZLsZQhSuxDszw@mail.gmail.com> <01R238XJND6O00004L@mauve.mrochek.com> <65cc0784-a8f0-e40e-c5d9-c736ee1081ea@digilicious.com> <01R23TPK47AA00004L@mauve.mrochek.com> <64374ebd-6a07-4463-7d3d-a232bd1a475a@digilicious.com>
To: Gene Hightower <gene@digilicious.com>
Archived-At: <https://mailarchive.ietf.org/arch/msg/ietf-smtp/XRRQ4iAcDPXNGVV2BxelzPDtVAs>
Subject: Re: [ietf-smtp] [Proposal] confusing parts of the mail system, was 250-MARKDOWN
X-BeenThere: ietf-smtp@ietf.org
X-Mailman-Version: 2.1.29
Precedence: list
List-Id: "Discussion of issues related to Simple Mail Transfer Protocol \(SMTP\) \[RFC 821, RFC 2821, RFC 5321\]" <ietf-smtp.ietf.org>
List-Unsubscribe: <https://www.ietf.org/mailman/options/ietf-smtp>, <mailto:ietf-smtp-request@ietf.org?subject=unsubscribe>
List-Archive: <https://mailarchive.ietf.org/arch/browse/ietf-smtp/>
List-Post: <mailto:ietf-smtp@ietf.org>
List-Help: <mailto:ietf-smtp-request@ietf.org?subject=help>
List-Subscribe: <https://www.ietf.org/mailman/listinfo/ietf-smtp>, <mailto:ietf-smtp-request@ietf.org?subject=subscribe>
X-List-Received-Date: Thu, 17 Jan 2019 13:41:26 -0000

> On 17/01/2019 04.29, Ned Freed wrote:

> > Clearly not, as you yourself have noted.

> Microsoft supports BINARYMIME for received mail on port 25.

> This something that, I hear, is very difficult for others to do.  I'm
> told it's very complicated.  Somehow they have figured out how to make
> this work.

They have not figured out how to make it work, because it's not possible to
make it work in general. Transcoding destroys DKIM signatures, period. So they
either:

(1) Reject messages sent with BINARYMIME and signatures, either in all cases
    or in cases where they know they are going to forward, leading to
    unncessary failures, or,

(2) Accept such messages and trash the signatures, leading to unnecessary
     failures, and,

(3) Deal with dynamic forwarding cases either by not having any or
    falling back to (1) or (2), leading to unnecessary failures.

My guess is that the number of BINARYMIME messages they get via SMTP is
so tiny they haven't had to deal with the problems. And of course since
the people attempting to send them BINARYMIME encounter problems they
probably give up on the extension.

				Ned