Valery,

Thanks for your review. Responses inline.


On 8/15/18 7:55 AM, Valery Smyslov wrote:
Hi,

here is my review of the document.

The draft is well written, however I found few places where it could be 
improved.

1. Section 2:

In the following para:

    In order to specify REQUIRETLS treatment for a given message, the
    REQUIRETLS option is specified on the MAIL FROM command when that
    message is transmitted.  This option MUST only be specified in the
    context of an SMTP session meeting the security requirements that
    have been specified:

The last sentence uses uppercase MUST, while in fact using MUST NOT is more
appropriate giving the meaning  of the sentence. I.e. "This option MUST NOT be
specified unless all the following requirements are met in the context of SMTP 
session:"

"MUST only" is logically equivalent to "MUST NOT...unless". Since they're equivalent, I have no objection to the wording you suggest, although IMO "MUST NOT...unless" is somewhat of a double negative as compared with "MUST only".

And in the following list I believe using uppercase words is unnecessary,
since they described not a protocol (REQUIRETLS) behavior, but
the requirements for REQUIRETLS to be used. I suggest changing
those MUSTs to lowercase.

    o  The session itself MUST employ TLS transmission.

    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 succesfully 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.

    o  Following the negotiation of STARTTLS, the SMTP server MUST
       advertise in the subsequent EHLO response that it supports
       REQUIRETLS.

I'm not claiming to be an expert on RFC 2119 usage, but the three MUSTs that you cite are absolute requirements of the specification. It could be worded to be more normative to the implementation of REQUIRETLS, that in order to send a message requiring TLS that the session MUST employ TLS transmission, verify certificates, and advertise its support of REQUIRETLS in STARTTLS sessions. But I still think that my use of uppercase MUST is proper. Other opinions?


2. I also have a question regarding the last bullet above - why advertising
REQUIRETLS is linked with negotiation of STARTTLS?
It is my understanding that TLS session may be established
without negotiation STARTTLS (as recommended by RFC8314),
so why the last bullet doesn't say just: "The SMTP server must
advertise in the EHLO response that it supports REQUIRETLS"?
Am I missing something here? The same question is applicable
to the first para in Section 4.3, where STARTTLS and REQUIRETLS are
also logically linked.

As Jeremy Harris pointed out while I was typing this, REQUIRETLS is only accepted within TLS-protected sessions. I had originally proposed advertising REQUIRETLS in all EHLO responses (TLS or not) as an optimization (don't bother negotiating STARTTLS if you have a message requiring TLS and the server doesn't support REQUIRETLS) but that wouldn't have been correct.

But you are correct that REQUIRETLS should be advertised in EHLO responses for all TLS-protected sessions, not just STARTTLS. Support for REQUIRETLS in such sessions was an afterthought on my part and I seem to have missed that adjustment here.

(and note a typo in a second bullet above: s/succesfully/successfully)

Thanks!

3. Section 8.1.

    REQUIRETLS is generally effective against passive attackers who are
    merely trying to eavesdrop on an SMTP exchange between an SMTP client
    and server.  This assumes, of course, the cryptographic integrity of
    the TLS connection being used.

I assume that it is encryption (and not an integrity) that protects
messages confidentiality against passive eavesdroppers, doesn't it?

I didn't mean content integrity -- I meant that the TLS session has integrity (i.e., is secure). But I can see how this might be interpreted as you have read it. Perhaps it should say "cryptographic security" rather than "cryptographic integrity".

-Jim

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