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From: Alexey Melnikov <alexey.melnikov@isode.com>
To: Ben Schwartz <bemasc@google.com>
Cc: "Salz, Rich" <rsalz@akamai.com>, "acme@ietf.org" <acme@ietf.org>
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Subject: Re: [Acme] WG last call for draft-ietf-acme-email-smime-06
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Hi Ben,

On 21/04/2020 01:12, Ben Schwartz wrote:
>
> On Wed, Apr 1, 2020 at 5:40 AM Alexey Melnikov
> <alexey.melnikov@isode.com <mailto:alexey.melnikov@isode.com>> wrote:
>
>     Hi Ben,
>
>     My apologies for missing your email in March:
>
>
> And mine for this delayed response.
>
>     On 12/03/2020 20:42, Ben Schwartz wrote:
>>     Section 3 says token-part1 "contains at least 64 bit of entropy",
>>     but Section 3.1 says token-part1 "MUST be at least 64 octet long
>>     after decoding".=C2=A0 Is this difference deliberate?
>
>     No, I obviously made a typo when saying octets. I will fix.
>
Fixed.
>
>>     Also 64 octets of entropy is a _lot_.=C2=A0 RFC 8555 says "the=C2=A0=
token
>>     is required to contain at least 128 bits of entropy".
>>
>>     The draft seems to be oriented entirely toward use with e-mail
>>     clients that have a built-in ACME-S/MIME client.=C2=A0 I'm a bit
>>     disappointed that the draft doesn't accommodate users with
>>     "naive" email clients very well, e.g. by allowing customized
>>     subject lines.
>
>     Actually, I was trying to accommodate naive email clients, but it
>     was a fine balance trying to specify minimal requirements.
>
>     Can you suggest some specific text to change and then we can
>     discuss whether or not it should be done? My thinking about the
>     Subject header field was that I wanted to have a unique subject
>     (so that ACME email messages are easily findable). I also wanted
>     to allow the token in the subject for APIs that can easily access
>     Subject and not other header fields.
>
> In that case, I would suggest "... subject ending with "(ACME:
> <token-part1>)", where ...".=C2=A0 That would allow the first part of t=
he
> subject (most likely to be seen by a human) to be human-readable.

After thinking a bit more about this:

As ACME servers are generating ACME challenge emails, the requirement on
them is stricter (they create the first message in an email thread). I
am tempted to leave this as is. Can you think of a case where ACME
servers would be unable to comply with this restriction?

ACME responses already allow arbitrary prefix to accommodate naive client=
s.

> Similarly, for Section 3.2. Point 6, I would relax the requirement to
> state that this block must appear somewhere in the body.=C2=A0 That way=
, if
> the user sees the response message, it can provide some explanation of
> what is going on.
Good idea. Changed.
> For Section 3.1 Point 5, I don't understand why the body is restricted
> to text/plain.=C2=A0 In particular, I think hyperlinks to explanations =
and
> instructions are likely to be helpful.=C2=A0 I also wonder whether supp=
ort
> for multipart/multilingual could be useful.
> The body is irrelevant to ACME-aware clients, so it seems like there
> could be a lot of freedom in how this is constructed.

This is true for the challenge email.

There is a requirement on S/MIME (if used) to provide header protection,
but I agree that otherwise the body structure can be pretty flexible.

> Most email clients automatically convert HTTPS URLs to hyperlinks,
> which should make the silly schemes I'm imagining possible,=C2=A0but no=
t
> very attractive, for ordinary users.
>
>     Best Regards,
>
>     Alexey
>
>>     I assume this is deliberate, perhaps because=C2=A0of a desire to u=
se
>>     short-TTL S/MIME certificates that would be impractical to
>>     provision manually, but the draft doesn't mention a rationale.
>>
>>     On Thu, Mar 12, 2020 at 2:52 PM Salz, Rich
>>     <rsalz=3D40akamai.com@dmarc.ietf.org
>>     <mailto:40akamai.com@dmarc..ietf.org>> wrote:
>>
>>         This mail begins a one-week working group last call on
>>         https://datatracker.ietf.org/doc/draft-ietf-acme-email-smime/?=
include_text=3D1
>>
>>         =C2=A0
>>
>>         If you have comments or issues, please post here.
>>
>>         =C2=A0
>>
>>         If anyone wants to be a document shepherd, please contact the
>>         chairs.
>>
Best Regards,

Alexey



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>
  </head>
  <body>
    <p>Hi Ben,<br>
    </p>
    <div class=3D"moz-cite-prefix">On 21/04/2020 01:12, Ben Schwartz
      wrote:<br>
    </div>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <meta http-equiv=3D"content-type" content=3D"text/html; charset=3DUTF-=
8">
      <div dir=3D"ltr"><br>
        <div class=3D"gmail_quote">
          <div dir=3D"ltr" class=3D"gmail_attr">On Wed, Apr 1, 2020 at 5:40
            AM Alexey Melnikov &lt;<a
              href=3D"mailto:alexey.melnikov@isode.com"
              moz-do-not-send=3D"true">alexey.melnikov@isode.com</a>&gt;
            wrote:<br>
          </div>
          <blockquote class=3D"gmail_quote" style=3D"margin:0px 0px 0px
            0.8ex;border-left:1px solid
            rgb(204,204,204);padding-left:1ex">
            <div>
              <p>Hi Ben,</p>
              <p>My apologies for missing your email in March:<br>
              </p>
            </div>
          </blockquote>
          <div><br>
          </div>
          <div>And mine for this delayed response.</div>
          <blockquote class=3D"gmail_quote" style=3D"margin:0px 0px 0px
            0.8ex;border-left:1px solid
            rgb(204,204,204);padding-left:1ex">
            <div>
              <p> </p>
              <div>On 12/03/2020 20:42, Ben Schwartz wrote:<br>
              </div>
              <blockquote type=3D"cite">
                <div dir=3D"ltr">
                  <div>Section 3 says token-part1 "<span
                      style=3D"color:rgb(0,0,0);font-size:13.3333px">contain=
s
                      at least 64 bit of entropy", but Section 3.1 says
                      token-part1 "</span>MUST be at least 64 octet long
                    after decoding".=C2=A0 Is this difference deliberate? <b=
r>
                  </div>
                </div>
              </blockquote>
              <p>No, I obviously made a typo when saying octets. I will
                fix.<br>
              </p>
            </div>
          </blockquote>
        </div>
      </div>
    </blockquote>
    Fixed.<br>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <div dir=3D"ltr">
        <div class=3D"gmail_quote">
          <blockquote class=3D"gmail_quote" style=3D"margin:0px 0px 0px
            0.8ex;border-left:1px solid
            rgb(204,204,204);padding-left:1ex">
            <div>
              <p> </p>
              <blockquote type=3D"cite">
                <div dir=3D"ltr">
                  <div>Also 64 octets of entropy is a _lot_.=C2=A0 RFC 8555
                    says "the=C2=A0token is required to contain at least 128
                    bits of entropy".</div>
                  <div><br>
                  </div>
                  <div>The draft seems to be oriented entirely toward
                    use with e-mail clients that have a built-in
                    ACME-S/MIME client.=C2=A0 I'm a bit disappointed that th=
e
                    draft doesn't accommodate users with "naive" email
                    clients very well, e.g. by allowing customized
                    subject lines. <br>
                  </div>
                </div>
              </blockquote>
              <p>Actually, I was trying to accommodate naive email
                clients, but it was a fine balance trying to specify
                minimal requirements.<br>
              </p>
              <p>Can you suggest some specific text to change and then
                we can discuss whether or not it should be done? My
                thinking about the Subject header field was that I
                wanted to have a unique subject (so that ACME email
                messages are easily findable). I also wanted to allow
                the token in the subject for APIs that can easily access
                Subject and not other header fields.</p>
            </div>
          </blockquote>
          <div>In that case, I would suggest "... subject ending with "(<spa=
n
              style=3D"color:rgb(0,0,0);font-size:13.3333px">ACME:
              &lt;token-part1&gt;)", where ...".=C2=A0 That would allow the
              first part of the subject (most likely to be seen by a
              human) to be human-readable.</span></div>
        </div>
      </div>
    </blockquote>
    <p>After thinking a bit more about this:<br>
    </p>
    <p>As ACME servers are generating ACME challenge emails, the
      requirement on them is stricter (they create the first message in
      an email thread). I am tempted to leave this as is. Can you think
      of a case where ACME servers would be unable to comply with this
      restriction?<br>
    </p>
    <p>ACME responses already allow arbitrary prefix to accommodate
      naive clients.<br>
    </p>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <div dir=3D"ltr">
        <div class=3D"gmail_quote">
          <div>Similarly, for Section 3.2. Point 6, I would relax the
            requirement to state that this block must appear somewhere
            in the body.=C2=A0 That way, if the user sees the response
            message, it can provide some explanation of what is going
            on.</div>
        </div>
      </div>
    </blockquote>
    Good idea. Changed.<br>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <div dir=3D"ltr">
        <div class=3D"gmail_quote">
          <div>For Section 3.1 Point 5, I don't understand why the body
            is restricted to text/plain.=C2=A0 In particular, I think
            hyperlinks to explanations and instructions are likely to be
            helpful.=C2=A0 I also wonder whether support for
            multipart/multilingual could be useful. <br>
          </div>
        </div>
      </div>
    </blockquote>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <div dir=3D"ltr">
        <div class=3D"gmail_quote">
          <div>The body is irrelevant to ACME-aware clients, so it seems
            like there could be a lot of freedom in how this is
            constructed.</div>
        </div>
      </div>
    </blockquote>
    <p>This is true for the challenge email.</p>
    <p>There is a requirement on S/MIME (if used) to provide header
      protection, but I agree that otherwise the body structure can be
      pretty flexible.<br>
    </p>
    <blockquote type=3D"cite"
cite=3D"mid:CAHbrMsAdXvpRt2zCUn7DLNerxhZCFe4pS0TM1qzmaCUGKVYT=3DA@mail.gmail=
.com">
      <div dir=3D"ltr">
        <div class=3D"gmail_quote">
          <div>Most email clients automatically convert HTTPS URLs to
            hyperlinks, which should make the silly schemes I'm
            imagining possible,=C2=A0but not very attractive, for ordinary
            users.</div>
          <blockquote class=3D"gmail_quote" style=3D"margin:0px 0px 0px
            0.8ex;border-left:1px solid
            rgb(204,204,204);padding-left:1ex">
            <div>
              <p>Best Regards,</p>
              <p>Alexey<br>
              </p>
              <blockquote type=3D"cite">
                <div dir=3D"ltr">
                  <div>I assume this is deliberate, perhaps because=C2=A0of =
a
                    desire to use short-TTL S/MIME certificates that
                    would be impractical to provision manually, but the
                    draft doesn't mention a rationale.</div>
                  <div><br>
                  </div>
                  <div class=3D"gmail_quote">
                    <div dir=3D"ltr" class=3D"gmail_attr">On Thu, Mar 12,
                      2020 at 2:52 PM Salz, Rich &lt;rsalz=3D<a
                        href=3D"mailto:40akamai.com@dmarc..ietf.org"
                        target=3D"_blank" moz-do-not-send=3D"true">40akamai.=
com@dmarc.ietf.org</a>&gt;
                      wrote:<br>
          =20         </div>
                    <blockquote class=3D"gmail_quote" style=3D"margin:0px
                      0px 0px 0.8ex;border-left:1px solid
                      rgb(204,204,204);padding-left:1ex">
                      <div lang=3D"EN-US">
                        <div>
                          <p class=3D"MsoNormal"><span
                              style=3D"font-size:11pt">This mail begins a
                              one-week working group last call on <a
href=3D"https://datatracker.ietf.org/doc/draft-ietf-acme-email-smime/?includ=
e_text=3D1"
                                target=3D"_blank" moz-do-not-send=3D"true">
https://datatracker.ietf.org/doc/draft-ietf-acme-email-smime/?include_text=
=3D1</a></span></p>
                          <p class=3D"MsoNormal"><span
                              style=3D"font-size:11pt">=C2=A0</span></p>
                          <p class=3D"MsoNormal"><span
                              style=3D"font-size:11pt">If you have
                              comments or issues, please post here.</span></=
p>
                          <p class=3D"MsoNormal"><span
                              style=3D"font-size:11pt">=C2=A0</span></p>
                          <p class=3D"MsoNormal"><span
                              style=3D"font-size:11pt">If anyone wants to
                              be a document shepherd, please contact the
                              chairs.</span></p>
                        </div>
                      </div>
                    </blockquote>
                  </div>
                </div>
              </blockquote>
            </div>
          </blockquote>
        </div>
      </div>
    </blockquote>
    <p>Best Regards,</p>
    <p>Alexey</p>
    <p><br>
    </p>
  </body>
</html>

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