Re: mail crypto, was the introduction problem, was Email

Christopher Morrow <morrowc.lists@gmail.com> Wed, 04 May 2022 20:40 UTC

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From: Christopher Morrow <morrowc.lists@gmail.com>
Date: Wed, 04 May 2022 16:40:37 -0400
Message-ID: <CAL9jLabiPFBm3KJTidtfnhHm8+r5q-sRSCt+TWZ6jyZKWjxq6Q@mail.gmail.com>
Subject: Re: mail crypto, was the introduction problem, was Email
To: Keith Moore <moore@network-heretics.com>
Cc: ietf <ietf@ietf.org>
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On Wed, May 4, 2022 at 4:20 PM Keith Moore <moore@network-heretics.com>
wrote:

> On 5/4/22 15:03, John Levine wrote:
>
> How much do we think 'transmitted in cleartext' exists anymore?
>
> TLS is still negotiated on a per-hop basis, and STARTTLS is subject to
> downgrading attacks from well-placed intermediaries.
>
> Only for domains that don't support MTA-STS or DANE TLSA.
>
> Fair point but I wonder how much it actually matters in practice.  I
> suppose setting up a "well-placed intermediary" is somewhat easier if you
> don't need an insider to give you access to the cleartext emails.  But
> having emails stored in cleartext on relaying SMTP servers still seems like
> a big vulnerability in today's world.
>
>
> I imagine that the bulk of mail sent/delivered is:
  1) between large mail providers (hotmail, gmail, etc)
  2) business-to-business

The 1st is certainly not (after a few well publicized incidents) storing
plaintext on disk for folk to read...
The second almost all use a form of 'exchange' that .. also doesn't store
plain text on disk...
  (and really the 2nd is subject to the employer/business having the remit
to review anyway...)