Hi, Jim,

On 21-07-17 12:56, Leif Johansson wrote:
There was clear consensus in Praha to adopt
draft-fenton-smtp-require-tls-03 as a WG document
(draft-ietf-uta-smtp-require-tls-00).

If anyone objects to that, now is the time to speak up.

no objection! Just wanted to send my review of -03 here:


Page 3:

Attacks are more described in more detail in the Security
   Considerations section of this document.

s/are more described/are described/

Page 3:

it also requires that the SMTP server advertise that it
   also supports REQUIRETLS


For some reason, I think that the second 'also' is not correct: the advertisement is done before the SMTP server 'knows' that the client is using REQUIRETLS.

Page 3 (sorry for the nitpicking):

in effect promising that it will honor the
   requirement to require TLS transmission and REQUIRETLS support for
   onward transmission of messages specifying that requirement.


Suggestion:
s/requirement to require/requirement to enforce/

And, referring to the first part of this sentence, you may want to:

s/transmission of messages specifying that requirement/transmission of those messages

Page 4:

this option MUST only be specified in the context
   of an SMTP session meeting the security requirements that have been
   specified:


Just for reasons of clarity, you might add a third bullet, which describes what already was mentioned earlier:

- the SMTP server advertises that it supports REQUIRETLS.

Page 5:

   3.  Establish a TLS-protected SMTP session with its peer SMTP server
       and authenticate the server's certificate with the specified
       authentication method.


you may want to add a reference to RFC6125 here.

Page 5:

   1.  Look up the SMTP server to which the message is to be sent.


A reference here to RFC5321 par. 5.1 would be nice, as in the remainder of this section it may not be clear for a developer that the absence of an MX record in the presence of an A record should be treated as an MX record with pref. 0 pointing to that host. You have this reference on page 6 in the REQUIRETLS=NO section so it would be consistent to add it here.

Page 6:

   Following such a failure, the SMTP client MUST send a non-delivery
   notification to the reverse-path of the failed messag


Reading this paragraph it seems there is no room for a client to postpone the decision to send a NDN, for example in case of a DNS tempfail.

Page 6:

   o  If the server does not advertise the REQUIRETLS capability, send
      the message in the usual manner (without the REQUIRETLS option,
      because the server will not understand the option).


There are circumstances where a middlebox may remove the REQUIRETLS advertisement and for these cases (in combination with REQUIRETLS=NO) it might still be useful to send the MAIL FROM with the REQUIRETLS option in order to convey the wish of the sender to send using a TLS encrypted channel. Comments?

Page 7:

   Mail delivery agents supporting REQUIRETLS SHOULD require that
   retrieval of messages requiring transport encryption take place over
   authenticated, encrypted channels.


AFAIK there is no mechanism where an MDA could require this from the Mail Access Server. Unless you mean the MDA should set some sort of flag, which then can be honored by the mail access server?

Page 8:

REQUIRETLS users SHOULD use caution
   when sending to mailing lists and MUST NOT assume that REQUIRETLS
   applies to messages from the list operator to list members.


Usually, users clicking on a 'Require encryption' button will not read this RFC and often do not even know whether a To: or Cc: mail address they use is a mailing list with specific characteristics. So I wonder if this line in the draft should better address the owner of the domain, recommending to educate their users not too expect (end2end) encryption in all cases.

Par. 7:

I wonder if a fourth attack vector should be mentioned: a DOS type of attack where an attacker uses REQUIRETLS, using the RFC5321.MailFrom address of a victim (using an MTA supporting REQUIRETLS) and sending messages to as many MTA's-not-supporting-REQUIRETLS it can find, resulting in a bombardment of the victim with NDN's. However, this type of DOS attack can be achieved already in other ways, so I think it need not be mentioned.

/rolf

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