[Uta] Benjamin Kaduk's Discuss on draft-ietf-uta-smtp-require-tls-08: (with DISCUSS and COMMENT)

[Benjamin Kaduk via Datatracker <[e-mail]>]

Benjamin Kaduk has entered the following ballot position for
draft-ietf-uta-smtp-require-tls-08: Discuss

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DISCUSS:
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I'm glad that we were able to come to consensus to rename the header
field to "TLS-Required"; that addresses a key concern of mine.

I  also appreciate the addition of the "Policy Conflicts" section that portrays
a fairly clear picture of the interaction between this mechanism, DANE, and
MTA-STS.  I still wish that we were able to bring the technologies into greater
alignment and not need to convey the sense that standards-track mechanisms
are in conflict with each other, but cannot justify blocking publication based
solely on that desire.
In this space, though, I do request an additional wording tweak in Appendix A.2,
which currently states "The TLS-Required header field is used when the sender
of the message wants to override the default policy of the recipient domain to
require TLS." which uses the "override" terminology without couching it as a
request.  Can we reword to include "request" here as well?

The following paragraph (unchanged from my ballot on -07) received only minimal
discussion so far:
I'm also concerned about the apparent new burden placed on senders in
Section 4.3 to actively decide whether every outgoing message requires
end-to-end TLS protection or is safe to forward without TLS ("when TLS
is to be required, [...].  When TLS is not to be required, [...]"), where both
"[...]" require new behavior not present in a client that does not implement
this specification.  To some extent this is an editorial matter of how the
new mechanisms are portrayed, but I don't see much in this document to justify
the stance that the default "don't care" option should be removed (for clients
that implement this specification at all).

It seems that we are in agreement that it's okay to have a "don't care" option,
which is indicated by not using the extension at all.  That said, I still think that
the specific text of Section 4.3 conveys an impression that there is a requirement
to actively decide, with the language about "has the authority to decide whether to
require TLS", "when TLS is  to be required", "when TLS is not to be required", and
"in either case, the decision [...] MAY be done based on [...]".   Perhaps I'm just misreading
the text, but I haven't seen any signals to that effect yet.  I'd suggest (but am open
to further refinement" changing to "has the option to decide whether to require TLS"
and "if one of these cases is selected, the decision [...]" as a way to clarify the language used.

[discussion of "de facto part of the core SMTP spec" removed, on  indications
that this is not the intent]

We had some good discussion about the three potential cases for authenticating
the TLS connection:
(1) Dane per RFC 7672
(2) MTA-STS per RFC 8461
(3) DNSSEC-validated MX records + WebPKI authentication of the MX hosts

I think a little more specificity is needed for the (3) case; we do say to use
the RFC 6125 procedures but still need to specify (e.g.) that the DNS-ID name
type is used and (IIRC) that the hostname resulting from the MX lookup is
used as the DNS-ID to be validated.


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COMMENT:
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[original comment section unchanged; contents likely to be stale]

Section 2

   o  The certificate presented by the SMTP server MUST either verify
      successfully in a trust chain leading to a certificate trusted by
      the SMTP client or it MUST verify successfully using DANE as
      specified in RFC 7672 [RFC7672].  For trust chains, the choice of
      trusted (root) certificates is at the discretion of the SMTP
      client.

I don't see how this requirement restricts the presented end-entity
certificate so as to eliminate the attacks that exploit "the lack of server
authentication by the client".  What does certificate have to name in order
to be trusted by the client?

Section 4.1

   Upon receipt of the REQUIRETLS option on a MAIL FROM command during
   the receipt of a message for which the return-path is not empty
   (indicating a bounce message), an SMTP server MUST tag that message
   as needing REQUIRETLS handling.

What processing should happen when REQUIRETLS is received and the
return-path *is* empty?

           If the REQUIRETLS MAIL FROM parameter is specified, the
   RequireTLS header field MUST be ignored but MAY be included in onward
   relay of the message.

How could this scenario arise?  (Why is it not a user error to attempt to
use both -- isn't one requiring TLS and the other disclaiming its use,
making them mutually incompatible?)

Section 4.2.1

   2.  If the server lookup is accomplished via the recipient domain's
       MX record (the usual case) and is not accompanied by a valid
       DNSSEC signature, the client MUST also validate the SMTP server
       name using MTA-STS as described in RFC 8461 [RFC8461]
       Section 4.1.

What happens if this validation fails?  Perhaps the below text "If any of
the above fails" could include "(including MTA-STS validation)" for extra
clarity.

   3.  Open an SMTP session with the peer SMTP server using the EHLO
       verb.

   4.  Establish a TLS-protected SMTP session with its peer SMTP server
       and authenticate the server's certificate as specified in
       [RFC6125] or [RFC7672] as applicable.

"STARTTLS" does not appear in here anywhere.
Separately, is this combination of steps going to preclude any setups that
(e.g., via preconfiguration) go straight to TLS with no STARTTLS
negotiation?

What name is used as input to certificate validation (for the 6125 branch)?
Is Appendix B.4 therein supposed to be normative?  (The Appendix B header
indicates that the content is non-normative.)

Section 4.2.2

   Some SMTP servers may be configured to require STARTTLS connections
   as a matter of policy and not accept messages in the absence of
   STARTTLS.  A non-delivery notification MUST be returned to the sender
   if message relay fails due to an inability to negotiate STARTTLS when
   required by the server.

This is an "inability to negotiate" combined with a rejection of
non-STARTTLS, right?

Section 5

   The path from the origination of an error bounce message back to the
   MAIL FROM address may not share the same REQUIRETLS support as the
   forward path.  Therefore, users requiring TLS are advised to make
   sure that they are capable of receiving mail using REQUIRETLS as

nit: "requiring TLS for outgoing mail"?

   If a REQUIRETLS message is bounced, the server MUST behave as if
   RET=HDRS was present as described in [RFC3461].  If both RET=FULL and
   REQUIRETLS are present, the RET=FULL MUST be disregarded and MAY be
   transformed to RET=HDRS on relay.  The SMTP client for a REQUIRETLS

If the MAY is not taken, will the next hop be obligated to detect that this
is a bounce and apply the preceding MUSTs?  If not, perhaps this also
should be a MUST?

   bounce message uses an empty MAIL FROM return-path as required by
   [RFC5321].  When the MAIL FROM return-path is empty, the REQUIRETLS
   parameter SHOULD NOT cause a bounce message to be discarded even if
   the next-hop relay does not advertise REQUIRETLS.

Perhaps an internal cross-reference up to Section 4.2.1 is in order?

   Senders of messages requiring TLS are advised to consider the
   possibility that bounce messages will be lost as a result of
   REQUIRETLS return path failure, and that some information could be
   leaked if a bounce message is not able to be transmitted with
   REQUIRETLS.

It's not really clear how actionable this is.  If you have a message
that you want to send, you're either going to send it or not send it.
What would you change about the message based on whether or not you
could get a bounce, or whether or not the bounce would leak the message
contents?

Section 6

   Mailing lists, upon receipt of a message, originate new messages to
   list addresses.  This is distinct from an aliasing operation that
   redirects the original message, in some cases to multiple recipients.

I'm not entirely sure how universally acknowledged this claim is; at
MIT, we have lots of "mailing lists" implemented via the central Moira
management database, but the actual implementation on the mailhubs is
more like the aliasing operation described in the second sentence.
Is there a need to make this distinction in order to support the
following points, or could they stand on their own without this?

   The requirement to preserve the REQUIRETLS tag therefore does not
   necessarily extend to mailing lists, although the inclusion of the
   RequireTLS header field MAY cause messages sent to mailing lists to
   inherit this characteristic.  [...]

Maybe I'm confused, but doesn't the REQUIRETLS tag and the RequireTLS
header field have very different characteristics?  I don't understand
which one "this characteristic" is supposed to refer to.

   Mailing list operators MAY apply REQUIRETLS requirements in incoming
   messages to the resulting messages they originate.  If this is done,
   they SHOULD also apply these requirements to administrative traffic,
   such as messages to moderators requesting approval of messages.

Maybe note that such administrative traffic can include message contents
intended for the list?

Section 8.2

   clear, where they can be intercepted.  REQUIRETLS detects the failure
   of STARTTLS and declines to send the message rather than send it
   insecurely.

nit: I'd say that REQUIRETLS requires the detection and declining,
rather than doing so itself.

                                                     REQUIRETLS requires
   successful certificate validation before sending the message.

(As mentioned above, we need greater clarity about what the validation
specifically entails.)

                 REQUIRETLS requires that the recipient domain's MX
   record lookup be validated either using DNSSEC or via a published
   MTA-STS policy that specifies the acceptable SMTP server hostname(s)
   for the recipient domain.

Are we then required to use those server hostname(s) in the certificate
validation portion of the TLS connection?

Section A.1

In light of https://www.iab.org/2016/11/07/iab-statement-on-ipv6/ please
consider using IPv6 examples.