[exim-dev] Re: [Bug 3021] New: patch: The essence of a MITM …

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Lähettäjä: Viktor Dukhovni via Exim-dev
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Vastaanottaja: exim-dev
Aihe: [exim-dev] Re: [Bug 3021] New: patch: The essence of a MITM is not that both I and the server still think I have an encrypted connection
On Wed, Aug 30, 2023 at 08:54:40AM +0100, Andrew C Aitchison via Exim-dev wrote:

> The patch does not clearly show the changed wording (diff is too
> interested in the changed line breaks) so here it is re-wrapped
> for human consumption:
>
> DNS-based Authentication of Named Entities, as applied to SMTP
> over TLS, provides assurance to a client that it is actually
> talking to the server it wants to rather than some attacker
> operating a Man In The Middle (MITM) operation.
> -The latter can terminate the TLS connection you make,
> -and make another one to the server (so both you and the server
> -still think you have an encrypted connection)
> +The latter can terminate the TLS connection you have with the server,
> +and make another one (so both you and the server
> +wrongly feel the encryption protects against interception)
> and, if one of the "well known" set of Certificate Authorities has
> been suborned - something which *has* been seen already (2014), a
> verifiable certificate (if you're using normal root CAs, eg. the
> Mozilla set, as your trust anchors).
>
> The new version suggests that a connection between me and the intended
> server starts and then ceases, so I would have to
> say this is worse than the original.


I concur that the suggested replacement is likely not an improvement.

> If we are going to make a change, the word 'terminate'
> is confusingly ambiguous. It is used here to indicate where
> one of the end points is, but it read as if an existing
> connection ceases.
>
> How about replacing the -+ text with:
>
> (A MITM attack creates a situation where both the client and
> the serverhave encrypted connections to the attacker but
> believe they are talking directly to each other)


This is noticeably better. It may make sense to first introduce the
concept of MiTM attacks, and then discuss how they're DANE addresses
them.

    Without additional counter-measures, SMTP is vulnerable to
    Man-in-The-Middle (MiTM) attacks:


        - At the DNS layer, by returning forged responses to MX
          lookups.


        - At the SMTP layer, by modifying the server's EHLO reply
          to suppress announcement of STARTTLS.  SMTP delivery then
          typically continues in the clear, and can be subject to
          further interference by the attacker.


        - At the TLS layer (in the absence of authentication, or by
          presenting a certificate for a forged MX hostname) by
          acting as the TLS server for the client's TLS connection,
          with the client unaware that it is encrypting a delivery
          to (or via) the attacker, rather than the intended
          destination.


    With DANE, and because DNSSEC is a prerequisite:


        - MX lookups are protected from tampering


        - TLSA record lookups are protected from modification or rogue
          denial of existence.


        - In the presence of (usable) TLSA records the client will
          use TLS or else will defer the delivery.


        - The real MX-host's published TLSA records will need to match
          the presented certificate chain, presumably not available to
          the MiTM attacker.


     In this way, DANE largely prevents MiTM attacks on email delivery
     from DANE-enabled SMTP clients to SMTP servers with MX and
     associated TLSA records published in DNSSEC zones.


     [ One underlying assumption, when DANE-TA(2) ("2 1 1" or
       similar) TLSA records are published by the server, is
       that is not easy to obtain a forged certificate from the
       associated CA.  Since DV certificate issuance is also
       potentially subject to MiTM attacks, some care is required
       to set up sufficiently strict CAA records, ideally require
       DNS challenges (protected via DNSSEC), ...


       For better security, publish exclusively DANE-EE(3) ("3 1 1" or
       similar) TLSA records. ]


Finally, a DANE SMTP server operator who does not implement *monitoring
of the certificate chain vs. published TLSA is not doing themselves or
the SMTP ecosystem a favour. Implement monitoring *before* you deploy
DANE:

https://list.sys4.de/hyperkitty/list/dane-users@list.sys4.de/thread/NKDBQABSTAAWLTHSZKC7P3HALF7VE5QY/

-- 
    Viktor.


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