[lamps] S/MIME 4+

Sean Turner <sean@sn3rd.com> Wed, 27 May 2026 15:26 UTC

Return-Path: <sean@sn3rd.com>
X-Original-To: spasm@mail2.ietf.org
Delivered-To: spasm@mail2.ietf.org
Received: from localhost (localhost [127.0.0.1]) by mail2.ietf.org (Postfix) with ESMTP id E9C7DF5FE43F for <spasm@mail2.ietf.org>; Wed, 27 May 2026 08:26:22 -0700 (PDT)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=ietf.org; s=ietf1; t=1779895582; bh=UyhBAt/hqXXSHIMlBCEa+wdVh4DS4f4zyCy5IhhYclY=; h=From:Subject:Date:To; b=QMjKhdEvxYFlyNBDKBuPj9ErhrcCAznaEE4itvJ34d8LGzIJxoPLxaBnL1R6HBTzG 0ezIlsalH49QcmgvKCAGxGB0R4a0K6SlNG63lXpQ4mT1hV5bVN1Vv0cg154ATj8Pqn 1YIRFucBjLJTjD/Fen/CKqAGTZIo0kGD5o3rGIXU=
X-Virus-Scanned: amavisd-new at ietf.org
X-Spam-Flag: NO
X-Spam-Score: -2.1
X-Spam-Level:
X-Spam-Status: No, score=-2.1 tagged_above=-999 required=5 tests=[BAYES_00=-1.9, DKIM_SIGNED=0.1, DKIM_VALID=-0.1, DKIM_VALID_AU=-0.1, DKIM_VALID_EF=-0.1, RCVD_IN_DNSWL_NONE=-0.0001, SPF_HELO_NONE=0.001, SPF_PASS=-0.001] autolearn=ham autolearn_force=no
Authentication-Results: mail2.ietf.org (amavisd-new); dkim=pass (1024-bit key) header.d=sn3rd.com
Received: from mail2.ietf.org ([166.84.6.31]) by localhost (mail2.ietf.org [127.0.0.1]) (amavisd-new, port 10024) with ESMTP id 66A1_hg6jnyj for <spasm@mail2.ietf.org>; Wed, 27 May 2026 08:26:22 -0700 (PDT)
Received: from mail-qv1-xf42.google.com (mail-qv1-xf42.google.com [IPv6:2607:f8b0:4864:20::f42]) (using TLSv1.3 with cipher TLS_AES_128_GCM_SHA256 (128/128 bits) key-exchange X25519 server-signature ECDSA (P-256) server-digest SHA256) (No client certificate requested) by mail2.ietf.org (Postfix) with ESMTPS id 5BD4EF5FE43A for <spasm@ietf.org>; Wed, 27 May 2026 08:26:22 -0700 (PDT)
Received: by mail-qv1-xf42.google.com with SMTP id 6a1803df08f44-8b4eb1fd5d0so144277586d6.0 for <spasm@ietf.org>; Wed, 27 May 2026 08:26:22 -0700 (PDT)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=sn3rd.com; s=google; t=1779895582; x=1780500382; darn=ietf.org; h=to:date:message-id:subject:mime-version:content-transfer-encoding :from:from:to:cc:subject:date:message-id:reply-to; bh=ueHYJj86h4OdFZII3PjMg1J3SUbvvHqEUoEPCDHcznM=; b=J8XA7ZsFjuGC7TB0DRLuRcb7gDY8mCkE9LOLx8j/Jfmchl3VoiHUh6Wt3iCeJ1xwSQ 7fXvCgHsJFA4VdT7gmi1zh/R66wROUUprCmcb+ny3onzwAXGsy4p5vbAYA+JCtg4S2Px IDf7h/fbXFI9yzuo5PlHCLsGXRzNtjtP8eSBU=
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=1e100.net; s=20251104; t=1779895582; x=1780500382; h=to:date:message-id:subject:mime-version:content-transfer-encoding :from:x-gm-gg:x-gm-message-state:from:to:cc:subject:date:message-id :reply-to; bh=ueHYJj86h4OdFZII3PjMg1J3SUbvvHqEUoEPCDHcznM=; b=pzsC8l4wLrikPIn18wNS60l1/Q5pNh9zj6hD2GEqbfxVgvc25TdBiYsZ7Kh7cLSs2+ tP88WrwtEov1ZTmMfkt0kn2UfQo/1nl51VtnoD+FIK80OkBPgAWLRHtVTfcxuldzV2yK pLt1tyffgBdLfZ6IrNw4s1IJYULdXCIdXbtaYpsA2kumABrtzcIIo/8VnHHctb3+1jP7 uc3SsqXvYpX7HDgrjRYc7P4pRo5HFqmTMPmX8c9CNxj203gmYz1KLT8kuAOqMiiWe3nw fbgABJQ4qy60PqU2LpK0sBzojl+fNUI4rMU5C0hBU5svZkO6haoszlRH1rRCmMNKD510 +C4g==
X-Gm-Message-State: AOJu0YxRQbCtVs1va1J83qYfIuAYuUSBMwNmYLFz+35MioLLVeb/XWbW rB9x1zCloilD1oVOhmZEQ298R7YS3SkcxvrY7hdYH8HQsLv6RAWpHo1nVW4UpsWfEZ4YDw/aht/ e2dr4RM58pA==
X-Gm-Gg: Acq92OGqfBwwAwMZDKjQMEbHedGnaDEsRIXOPuQZ319PgS/sZuLjL1wNJjtXmaPh/bE KoBuuYpqxJbKcBfjkIhmX0nMA9QI3QS+P4AuKrwh+UHn88hEHWKFcuoDd1QUWDuDESKYTnguOhB A9OEdViPxhTU1XlNlZw85X3zJ5fJA/S1ohQSx2CdVqBVwd1cXevXSMhhiJZjoX2Q9i3KHj6QNi2 gOmUiz0mSJ8rtbqied1OAptrpYAD4zRKBawFoMvXNuu4bwgcx0NkhQLWQI6NN3AmNd/DKcj9TW4 VdPIqAEkP0IYNta/MXDcH+sI6pzGE2VS5zGbl548irDFOu70wOEsmyG9Bni1LlYRfoZ1GAOeSLq S30vzvoC70Du//FgNxrxwQeKlovQwZ2NLW1uJMco7NCOe9YAARKYiLylDOYTDysZC0OVJG7Nops 0xzGdZ6RHac/lOhhq5Xn+FZdWDe81to0n4aGMP00okbdq5Xcag
X-Received: by 2002:a05:6214:4892:b0:8ac:a6bd:503b with SMTP id 6a1803df08f44-8cc7b550e40mr385014076d6.15.1779895581598; Wed, 27 May 2026 08:26:21 -0700 (PDT)
Received: from smtpclient.apple ([2600:4040:2528:6b00:417f:6a5b:c41c:18b7]) by smtp.gmail.com with ESMTPSA id 6a1803df08f44-8cc8132429bsm172723196d6.47.2026.05.27.08.26.21 for <spasm@ietf.org> (version=TLS1_2 cipher=ECDHE-ECDSA-AES128-GCM-SHA256 bits=128/128); Wed, 27 May 2026 08:26:21 -0700 (PDT)
From: Sean Turner <sean@sn3rd.com>
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: quoted-printable
Mime-Version: 1.0 (Mac OS X Mail 16.0 \(3864.600.51.1.1\))
Message-Id: <245DAA91-BD42-4095-A39D-133E06EC9041@sn3rd.com>
Date: Wed, 27 May 2026 11:26:00 -0400
To: IETF LAMPS <spasm@ietf.org>
X-Mailer: Apple Mail (2.3864.600.51.1.1)
Message-ID-Hash: P35GLKV4MEZMEVM7J2XMM2IJBQ7DYB73
X-Message-ID-Hash: P35GLKV4MEZMEVM7J2XMM2IJBQ7DYB73
X-MailFrom: sean@sn3rd.com
X-Mailman-Rule-Misses: dmarc-mitigation; no-senders; approved; emergency; loop; banned-address; member-moderation; header-match-spasm.ietf.org-0; nonmember-moderation; administrivia; implicit-dest; max-recipients; max-size; news-moderation; no-subject; digests; suspicious-header
X-Mailman-Version: 3.3.9rc6
Precedence: list
Subject: [lamps] S/MIME 4+
List-Id: This is the mail list for the LAMPS Working Group <spasm.ietf.org>
Archived-At: <https://mailarchive.ietf.org/arch/msg/spasm/jXUBk7G78vLoOgZZWN2_vrGbu-A>
List-Archive: <https://mailarchive.ietf.org/arch/browse/spasm>
List-Help: <mailto:spasm-request@ietf.org?subject=help>
List-Owner: <mailto:spasm-owner@ietf.org>
List-Post: <mailto:spasm@ietf.org>
List-Subscribe: <mailto:spasm-join@ietf.org>
List-Unsubscribe: <mailto:spasm-leave@ietf.org>

Hi! Blake and I submitted drafts that we are hoping will be the basis for S/MIME 4+. Four things I would like to draw your attention to:

1. Authors

Jim Schaad passed away in 2020. Out of acknowledgement for the amount of work he put into previous versions, we have moved him to the new "Contributors” section.

2. Formatting

The drafts are as close to RFCs 8550 & 8551 as I could get them; previous versions had some formatting that I could not recreate with the current tools (s7.1 in RFCs 8550 & 8551 was moved to s1.2 in the bis drafts). We can then make changes and everybody can then see what’s changed. Drafts are here:

https://datatracker.ietf.org/doc/draft-turner-lamps-rfc8550bis/
https://datatracker.ietf.org/doc/draft-turner-lamps-rfc8551bis/

Diffs to RFCs 8550 & 8551 are here:

https://author-tools.ietf.org/iddiff?url1=rfc8550&url2=draft-turner-lamps-rfc8550bis-00&difftype=--html
https://author-tools.ietf.org/iddiff?url1=rfc8551&url2=draft-turner-lamps-rfc8551bis-00&difftype=--html

3. Version Number

I picked 4+ because how much we change will dictate what number we use.

4. Changes to Incorporate !?!

I started an issue to track what we are going to change - we can then create sub-issues to track each one we agree to do; see https://github.com/seanturner/smime/issues/1.

The one thing I absolutely sure we need to include in this update is a “fix” that addresses the Falco attack; see https://github.com/seanturner/smime/issues/2. BUT, the question is do we do that simply by requiring signed attributes always be present or do we do what -cms-euf-cma-signeddata recommends for new protocols and use the id-ct-mimeData content type?

I am sure others will come up with more, but here are more changes to consider:
    • Deprecate use of EnvelopedData except for backward compatibility?
    • Deprecate RSA encryption?
    • Keep RSA-OAEP?
    • Add PQ algorithms?
    • Drop ’88 ASN.1 Module?

Let the games begin!

Cheers,
spt