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Happy new year to all participants!


On Fri 31/Dec/2021 21:01:40 +0100 John C Klensin wrote:
> 
> (2) Section 2.3.11 says "address normally consists of user and
> domain specifications".   Given other things we have tightened
> up and the submission server cases, "normally" may be a source
> of confusion.  Should it be dropped or the phrase changed to
> "except in the special case of 'postmaster' (Section 2.3.5) an
> address consists of user and domain specifications..." ?


IMHO Section 2.3.11 is good as is.  However, a paragraph recalling that 
postmaster has to be accepted by the MTA software and its actual mailbox 
defined as an alias would be a cool improvement.  Perhaps, some subsection of 
Section 3.4 is a better place than 2.3.11 for that.


> (4) While Section 5.1 has been fairly significantly overhauled,
> it may still be confusing and may need more work.


Maybe it's me, but the following sentence seems to be wrong.  Its meaning is 
clear (to me) but the language sounds lacking:

                    If there are no records left at that point, it is an
    error condition, and a 5yz reply code generated (terminating the mail
    transaction) or the message MUST be returned as undeliverable.


Best
Ale
-- 





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From: John C Klensin <john-ietf@jck.com>
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--On Saturday, January 1, 2022 18:35 +0100 Alessandro Vesely
<vesely@tana.it> wrote:

> Happy new year to all participants!

Happy new year to you and others too.
 
> On Fri 31/Dec/2021 21:01:40 +0100 John C Klensin wrote:
>> 
>> (2) Section 2.3.11 says "address normally consists of user and
>> domain specifications".   Given other things we have tightened
>> up and the submission server cases, "normally" may be a source
>> of confusion.  Should it be dropped or the phrase changed to
>> "except in the special case of 'postmaster' (Section 2.3.5) an
>> address consists of user and domain specifications..." ?

> IMHO Section 2.3.11 is good as is.  However, a paragraph
> recalling that postmaster has to be accepted by the MTA
> software and its actual mailbox defined as an alias would be a
> cool improvement.  Perhaps, some subsection of Section 3.4 is
> a better place than 2.3.11 for that.

That becomes a question of how often we should say it and when
repeating it becomes irritating noise.  Section 2.3.5 does
mention it, 4.1.1.3 talks about it again, and there is an
extended discussion along with an explicit "MUST be supported"
in 4.5.1.

Personal opinion: if we don't drop "normally", we are covered.
If we remove "normally", maybe we should mention the
"postmaster" case as I suggested in my note (maybe with
additional references to 4.1.1.3 and 4.5.1 but that could also
be getting tedious).  But going as far as adding a paragraph to
2.3.11 seems repetitive to me.  As to 3.4, I was already
concerned when I rearranged it that things were creeping in
there that don't belong.  While one could configure a local
system to treat "postmaster" or
"postmaster@local-domain.example" as an alias for some local
user/administrator or set of them, there is nothing in the spec,
and probably should not be, that requires it to treated as
anything but the name of a local mailbox.  So, if more is
needed, not in 3.4.
 
>> (4) While Section 5.1 has been fairly significantly
>> overhauled, it may still be confusing and may need more work.
> 
> 
> Maybe it's me, but the following sentence seems to be wrong.
> Its meaning is clear (to me) but the language sounds lacking:
> 
>                     If there are no records left at that
> point, it is an
>     error condition, and a 5yz reply code generated
> (terminating the mail
>     transaction) or the message MUST be returned as
> undeliverable.

It was moved from somewhere else and slightly enhanced. The text
was awkward in its original form and location, but is, IMO, no
worse in the current ones.  I considered some alternatives, but
they got a lot longer.  On the other hand, that might have just
been my lack of imagination when I was working on those sections.

Suggestions of replacement text welcome.  

best,
   john


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It appears that John C Klensin  <klensin@jck.com> said:
>(1) This is mostly just a heads-up for people suggesting new
>text, but "host name" (with "primary" in front of, whatever that
>means, is [still] defined in Section 2.3.5 as "a domain name
>that resolves to an address RR".  As I have understood it, that
>means no labels with CNAME records and no labels with only MX
>and no A RRs.

I fear that the least bad thing we can do is to leave host names alone
and say you can in principle send mail to any LDH domain that has an
address or MX or a CNAME that resolves to one.  This does not make
me happy but I can't think of any alternatives that don't make me
even less happy.

>Section 2.3.5 clearly says "one or more components" and then
>goes on to say
>	"This makes the requirement, described in more detail
>	below, that only fully-qualified domain names appear in
>	SMTP transactions on the public Internet, particularly
>	important where top-level domains are involved."
>
>but does not spell out any issues with those names -- the
>sentence was apparently intended to avoid a historical problem
>in which single-label FQDNs have been confused with abbreviated
>names 

Yeah, that was the .CS problem

(which 5321bis no longer addresses).  They have also, IIR,
>caused considerable discussion within ICANN as to whether they
>should be permitted in the root. 

No contracted TLDs have an A or MX and I am pretty sure that none
of them are asking for an exception.  As we reported eight years
ago in RFC 7085, a fair number of ccTLDs do have an A or an MX
but as far as I can tell none of them actually accept mail except
perhaps .AI for the address n@ai.  Some are just strange, notably
that .GT and .TT had MX's pointed at Gmail for nearly a decade,
without as far as I can tell ever asking Google if that was a
good idea.

Can 5321bis just say that the domain must always be a FQDN and
an applicability statement say that single-component domains
don't work reliably in mail addresses?

R's,
John


From nobody Sat Jan  1 14:39:37 2022
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Date: Sat, 01 Jan 2022 17:39:22 -0500
From: John C Klensin <john-ietf@jck.com>
To: John Levine <johnl@taugh.com>, emailcore@ietf.org
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--On Saturday, January 1, 2022 17:07 -0500 John Levine
<johnl@taugh.com> wrote:

> It appears that John C Klensin  <klensin@jck.com> said:
>> (1) This is mostly just a heads-up for people suggesting new
>> text, but "host name" (with "primary" in front of, whatever
>> that means, is [still] defined in Section 2.3.5 as "a domain
>> name that resolves to an address RR".  As I have understood
>> it, that means no labels with CNAME records and no labels
>> with only MX and no A RRs.
> 
> I fear that the least bad thing we can do is to leave host
> names alone and say you can in principle send mail to any LDH
> domain that has an address or MX or a CNAME that resolves to
> one.  This does not make me happy but I can't think of any
> alternatives that don't make me even less happy.

AFAICT, that is what the spec says now, the little peculiarity
that seems to ban single-label names notwithstanding.

>> Section 2.3.5 clearly says "one or more components" and then
>> goes on to say
>>	"This makes the requirement, described in more detail
>>	below, that only fully-qualified domain names appear in
>>	SMTP transactions on the public Internet, particularly
>>	important where top-level domains are involved."
>> 
>> but does not spell out any issues with those names -- the
>> sentence was apparently intended to avoid a historical problem
>> in which single-label FQDNs have been confused with
>> abbreviated names 
> 
> Yeah, that was the .CS problem

Not quite.  The CS problem, at least as I saw it play out, had
to do with abbreviating tom.cs.univ.edu, dick.cs.univ.edu, etc.,
as "tom.cs" and "dick.cs" to distinguish them from
tom.phy.univ.edu and dick.math.univ.edu.  When "CS" became a
valid TLD, the systems within that university that were calmly
mapping tom.cs to tom.cs.univ.edu prevented access to, e.g.,
jakub.cs.

>> (which 5321bis no longer addresses).  They have also, IIR,
>> caused considerable discussion within ICANN as to whether they
>> should be permitted in the root. 
> 
> No contracted TLDs have an A or MX and I am pretty sure that
> none of them are asking for an exception.  As we reported
> eight years ago in RFC 7085, a fair number of ccTLDs do have
> an A or an MX but as far as I can tell none of them actually
> accept mail except perhaps .AI for the address n@ai.  Some are
> just strange, notably that .GT and .TT had MX's pointed at
> Gmail for nearly a decade, without as far as I can tell ever
> asking Google if that was a good idea.
> 
> Can 5321bis just say that the domain must always be a FQDN and
> an applicability statement say that single-component domains
> don't work reliably in mail addresses?

5321bis says that now.  And I agree that the A/S the right place
to address "don't work reliably".

thanks,
  john


From nobody Thu Jan  6 12:29:14 2022
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Author: Steffen Nurpmeso <steffen@sdaoden.eu>
From: Steffen Nurpmeso <steffen@sdaoden.eu>
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Subject: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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Hello.

It is not only IPv6, it also cloud services.
And it is that ever changing TTL in times of DNS responsibility
indirection a.k.a. content delivery.  Worse, if i bypass my local
DNS cache and for example say "dig XXX @8.8.8.8" then for the same
host i do get the same IP, but the TTL is 159, 208, 134.
These rotations surely have an impact on RFC 6647, 5.,

   1.  Implement greylisting based on a tuple consisting of (IP address,
       RFC5321.MailFrom, and the first RFC5321.RcptTo).

that was not forseeable to this extent in 2012?
It seems greylisting now mask /8 for IPv4 and /64 for IPv6.
It seems to me when generating X different messages in the
delay/retry time frame Y, the message X+1 "unlocks" sent before.

As i am in the process of writing a greylisting policy server (for
postfix policy protocol) i wonder how future proof this can be,
without adding more identification tokens to early stages of the
SMTP protocol?
With the caveat that i (am) personally (not an administrator and)
sit in a small corner of the internet with only a *very* limited
view onto the overall SMTP traffic.  How useful is greylisting on
overall and/or on this scale today, and tomorrow?

--steffen
|
|Der Kragenbaer,                The moon bear,
|der holt sich munter           he cheerfully and one by one
|einen nach dem anderen runter  wa.ks himself off
|(By Robert Gernhardt)


From nobody Thu Jan  6 12:58:57 2022
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Date: Thu, 06 Jan 2022 15:58:43 -0500
From: John C Klensin <john-ietf@jck.com>
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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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--On Thursday, January 6, 2022 21:29 +0100 Steffen Nurpmeso
<steffen@sdaoden.eu> wrote:

> Hello.
> 
> It is not only IPv6, it also cloud services.
> And it is that ever changing TTL in times of DNS responsibility
> indirection a.k.a. content delivery.  Worse, if i bypass my
> local DNS cache and for example say "dig XXX @8.8.8.8" then
> for the same host i do get the same IP, but the TTL is 159,
> 208, 134. These rotations surely have an impact on RFC 6647,
> 5.,
> 
>    1.  Implement greylisting based on a tuple consisting of
> (IP address,        RFC5321.MailFrom, and the first
> RFC5321.RcptTo).
> 
> that was not forseeable to this extent in 2012?
> It seems greylisting now mask /8 for IPv4 and /64 for IPv6.
> It seems to me when generating X different messages in the
> delay/retry time frame Y, the message X+1 "unlocks" sent
> before.
> 
> As i am in the process of writing a greylisting policy server
> (for postfix policy protocol) i wonder how future proof this
> can be, without adding more identification tokens to early
> stages of the SMTP protocol?
> With the caveat that i (am) personally (not an administrator
> and) sit in a small corner of the internet with only a *very*
> limited view onto the overall SMTP traffic.  How useful is
> greylisting on overall and/or on this scale today, and
> tomorrow?

Steffen,

Am I correct to suggest that this is a topic for either a
6647bis or for comments on the subject in the developing
EMAILCORE A/S that might update 6647bis -- neither of which is
obviously in scope with this WG at the moment-- and not
something you believe should be addressed in 5321bis?

thanks,
   john


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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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It appears that Steffen Nurpmeso  <steffen@sdaoden.eu> said:
>These rotations surely have an impact on RFC 6647, 5.,
>
>   1.  Implement greylisting based on a tuple consisting of (IP address,
>       RFC5321.MailFrom, and the first RFC5321.RcptTo).
>
>that was not forseeable to this extent in 2012?

Item 5 in section 5 says:

       To accommodate those senders that have clusters of outgoing mail
       servers, greylisting servers MAY track CIDR blocks of a size of
       its own choosing, such as /24, rather than the full IPv4 address.
       (Note, however, that this heuristic will not work for clusters
       having machines on different networks.)  A similar grouping
       capability MAY be established based on the domain name of the
       mail server if one can be determined.

Is this the problem you are encountering or something else?

In my experience, allowing matches within a /24 in IPv4 or a /64
in IPv6 largely addresses this problem.

>How useful is greylisting on
>overall and/or on this scale today, and tomorrow?

My small system recently greylisted 21238 sending hosts of which 12745
retried and 8770 didn't. Once a host retries, it isn't greylisted
again unless it hasn't sent any mail for over a month. Spot checks
show that the 40% of hosts that don't retry are almost all spambots,
so it's useful, but not so much we'd change the protocol.

Apropos jck's question, while we might consider revising 6447, this has nothing
to do with 5321 so replies are directed to the ietf-smtp list.

R's,
John


From nobody Thu Jan  6 15:23:09 2022
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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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John C Klensin wrote in
 <001C904B1B67B2632182BF8D@PSB>:
 |--On Thursday, January 6, 2022 21:29 +0100 Steffen Nurpmeso
 |<steffen@sdaoden.eu> wrote:
 ..
 |> 208, 134. These rotations surely have an impact on RFC 6647,
 |> 5.,
 ...
 |Steffen,
 |
 |Am I correct to suggest that this is a topic for either a
 |6647bis or for comments on the subject in the developing
 |EMAILCORE A/S that might update 6647bis -- neither of which is
 |obviously in scope with this WG at the moment-- and not
 |something you believe should be addressed in 5321bis?

I well heared the respect from everyone that you managed to
publish draft 8 with all the formal bells and whistles that IETF
imposes before new year's eve, i am too much living on a sideshow
to have even considered to say "Congratulations" or "Thank you"
(though especially the latter would really be due).
(It was just that idea to "throw a problem into a forum".)

--steffen
|
|Der Kragenbaer,                The moon bear,
|der holt sich munter           he cheerfully and one by one
|einen nach dem anderen runter  wa.ks himself off
|(By Robert Gernhardt)


From nobody Fri Jan  7 12:45:34 2022
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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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On 2022-01-06 15:06, John Levine wrote:
> It appears that Steffen Nurpmeso<steffen@sdaoden.eu>  said:
>> These rotations surely have an impact on RFC 6647, 5.,
>>
>>    1.  Implement greylisting based on a tuple consisting of (IP address,
>>        RFC5321.MailFrom, and the first RFC5321.RcptTo).
>>
>> that was not forseeable to this extent in 2012?
> Item 5 in section 5 says:
> 
>         To accommodate those senders that have clusters of outgoing mail
>         servers, greylisting servers MAY track CIDR blocks of a size of
>         its own choosing, such as /24, rather than the full IPv4 address.
>         (Note, however, that this heuristic will not work for clusters
>         having machines on different networks.)  A similar grouping
>         capability MAY be established based on the domain name of the
>         mail server if one can be determined.
> 
> Is this the problem you are encountering or something else?
> 
> In my experience, allowing matches within a /24 in IPv4 or a /64
> in IPv6 largely addresses this problem.
> 

In my experience, SPF is really useful too as you can treat multiple 
delivery attempts that achieve a SPF:PASS to be identical, such that I 
don't have to care whether the sender uses a cluster across multiple IP 
Addresses.

This would seem to be a handy way to identify a "similar grouping 
capability" for senders that use SPF without manual effort.



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From: Hector Santos <hsantos@isdg.net>
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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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On 1/6/2022 3:58 PM, John C Klensin wrote:
>
> Steffen,
>
> Am I correct to suggest that this is a topic for either a
> 6647bis or for comments on the subject in the developing
> EMAILCORE A/S that might update 6647bis -- neither of which is
> obviously in scope with this WG at the moment-- and not
> something you believe should be addressed in 5321bis?
>

 From a technical standpoint, RFC5321bis should take into account 
basic implementation considerations used in the "pseudo-standard" 
greylist protocol that are at least 19+ years old showing two 
essential SMTP ideas:

- Timely delivery with minimal delays,
- Meaningful structured retry responses to advance intelligent SMTP 
clients.

The draft SMTP GreyList extension addresses these two basic SMTP 
advancement ideas:

      https://tools.ietf.org/id/draft-santos-smtpgrey-02.html

    GREYLIST is a SMTP extension to formalize the widely supported
    Greylisting mail filtering method and to help support SMTP rejected
    transports by following a new formal structured 4yz server temporary
    rejection response by including a "retry=time-delay" tag string which
    SMTP clients can use to optimize the rescheduling of the mail
    delivery attempts.  With adoption, network overhead reduction in
    wasteful mail delivery attempts will be realized.



Perhaps updating RFC5321bis examples showing real responses that exist 
in the market that include include "Retry Hints" as outlined in the 
draft.

There is running code that use the GreyList SMTP Extension retry hints.

Note: The informational RFC6647 was being drafted at the time the SMTP 
GreyList extension draft was being written.  I took it as a rebuttal 
against my greylisting work and in fact, it provided an opinion 
(without any stats to back it up) that "Retry Hints" presented a 
security risk to DoS attacks.  There was no evidence of this then, nor 
is there any evidence of this today. But the damage was done for any 
further IETF work for the proposed SMTP extension to help formalized 
Greylisting. All responsible systems, regardless of GreyListing, is 
already handling DoS attacks in some secured fashion.

Whether the improved RFC5321bis "SMTP Handbook" should codify 
important modern SMTP transport implementation ideas used in practice, 
I leave to others to decide.

I do agree, 100%, RFC6647bis should remove its guidance against 
structured Greylist reply text.


-- 
Hector Santos,
https://winserver.com/public/spamstats.wct




From nobody Sat Jan 15 06:17:58 2022
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Date: Sat, 15 Jan 2022 15:17:47 +0100
Author: Steffen Nurpmeso <steffen@sdaoden.eu>
From: Steffen Nurpmeso <steffen@sdaoden.eu>
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Subject: Re: [Emailcore] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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Hello.

Sorry for the late reply, i wanted to read the draft first.
(The thread continued on ietf-smtp@ due to request.) 

Hector Santos wrote in
 <61E049C9.3070906@isdg.net>:
 |On 1/6/2022 3:58 PM, John C Klensin wrote:
 |> Am I correct to suggest that this is a topic for either a
 |> 6647bis or for comments on the subject in the developing
 |> EMAILCORE A/S that might update 6647bis -- neither of which is
 |> obviously in scope with this WG at the moment-- and not
 |> something you believe should be addressed in 5321bis?
 |
 | From a technical standpoint, RFC5321bis should take into account 
 |basic implementation considerations used in the "pseudo-standard" 
 |greylist protocol that are at least 19+ years old showing two 
 |essential SMTP ideas:
 |
 |- Timely delivery with minimal delays,
 |- Meaningful structured retry responses to advance intelligent SMTP 
 |clients.
 |
 |The draft SMTP GreyList extension addresses these two basic SMTP 
 |advancement ideas:
 |
 |      https://tools.ietf.org/id/draft-santos-smtpgrey-02.html

I think the idea of a retry=[MIN:]SEC member in the deferral
response is interesting, even though i do not know how MTAs manage
their queues .. but likely they could adapt to this easily.
It could be used to avoid useless traffic, which in today's
greylisting practice as i experience it happens, even multiple
times, before the message gets through.

 |    GREYLIST is a SMTP extension to formalize the widely supported
 |    Greylisting mail filtering method and to help support SMTP rejected
 |    transports by following a new formal structured 4yz server temporary
 |    rejection response by including a "retry=time-delay" tag string which
 |    SMTP clients can use to optimize the rescheduling of the mail
 |    delivery attempts.  With adoption, network overhead reduction in
 |    wasteful mail delivery attempts will be realized.
 |
 |Perhaps updating RFC5321bis examples showing real responses that exist 
 |in the market that include include "Retry Hints" as outlined in the 
 |draft.
 |
 |There is running code that use the GreyList SMTP Extension retry hints.
 |
 |Note: The informational RFC6647 was being drafted at the time the SMTP 
 |GreyList extension draft was being written.  I took it as a rebuttal 
 |against my greylisting work and in fact, it provided an opinion 
 |(without any stats to back it up) that "Retry Hints" presented a 
 |security risk to DoS attacks.  There was no evidence of this then, nor 
 |is there any evidence of this today. But the damage was done for any 
 |further IETF work for the proposed SMTP extension to help formalized 
 |Greylisting. All responsible systems, regardless of GreyListing, is 
 |already handling DoS attacks in some secured fashion.
 |
 |Whether the improved RFC5321bis "SMTP Handbook" should codify 
 |important modern SMTP transport implementation ideas used in practice, 
 |I leave to others to decide.
 |
 |I do agree, 100%, RFC6647bis should remove its guidance against 
 |structured Greylist reply text.

--steffen
|
|Der Kragenbaer,                The moon bear,
|der holt sich munter           he cheerfully and one by one
|einen nach dem anderen runter  wa.ks himself off
|(By Robert Gernhardt)


From nobody Sat Jan 15 10:27:46 2022
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Date: Sat, 15 Jan 2022 19:27:31 +0100
Author: Steffen Nurpmeso <steffen@sdaoden.eu>
From: Steffen Nurpmeso <steffen@sdaoden.eu>
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Subject: Re: [Emailcore] [ietf-smtp] Status of Greylisting (i'd wish MessageID were part of SMTP prologue)
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John Levine wrote in
 <20220115180055.E4C0634FF1B1@ary.qy>:
 |It appears that Steffen Nurpmeso  <steffen@sdaoden.eu> said:
 |>I think the idea of a retry=[MIN:]SEC member in the deferral
 |>response is interesting, even though i do not know how MTAs manage
 |>their queues .. but likely they could adapt to this easily.
 |
 |This is not a new suggestion, and nobody I know has ever implemented it
 |other than as small scale experiments.  The point of greylisting is to
 |test the retry logic that every real MTA already has, not to invent
 |yet another hack on the client side.

I think that "Free at last! Free at last!" is still current, yes.

 |MTAs run their own retry schedules and it would generally not be easy
 |to have special schedules for specific messages.

Well like i said, i do not know.  Every MTA needs to have
a per-cache-entry notion and likely a per-receiver one, too.
It should thus naturally be capable to skip over one or multiple
deliveries, if the retry= suggests that it is useless to try
earlier.  Noone said it must try exactly after the "retry"
duration, only that it does not make sense to try earlier.
So if that would be implemented, why not?

Of course admins may then decide to greylist multiple times
nonetheless.
And it all does not help to be able to "exactly" identify
a message in order to perform real greylisting.

--steffen
|
|Der Kragenbaer,                The moon bear,
|der holt sich munter           he cheerfully and one by one
|einen nach dem anderen runter  wa.ks himself off
|(By Robert Gernhardt)


From nobody Sat Jan 15 12:11:14 2022
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From: John C Klensin <john-ietf@jck.com>
To: Steffen Nurpmeso <steffen@sdaoden.eu>, emailcore@ietf.org
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Subject: [Emailcore] New idea postings to this list (was: Re: Status of Greylisting (i'd wish MessageID were part of SMTP prologue))
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Steffen (and Hector),

I don't mean to pick on you and hope this note is not taken as
doing that, but...

Unless one of you, or someone else, wants to make a strong case
for discussing Greylisting in 5321bis (or 5322bis) I hope there
are no further discussions on this list.

Procedurally, discussing it in either of those documents would
require either:

 * Publishing one or both of them at Proposed Standard,
	countering the main justification for this WG.

or

 * Pausing the WG's work while an updated, preferably
	Standards Track, version of RFC 6647 is written, works
	its way through the system and then, IIR no less that
	six months after publication, an implementation report
	is generated that justifies moving it to full standard.
	Or new specifications, documenting new ideas, are moved
	through the system on the same basis.

I would not feel so strongly about this except that, with a
grand total of zero comments on the changes and questions raised
in draft-ietf-emailcore-rfc5321bis-08 since it was posted two
weeks ago, I am feeling very concerned that, except for
discussions on new ideas like these or arguments about document
organization, the WG is running out of energy already and, more
important, that there may not be sufficient energy to do the
comprehensive reviews that Internet Standard Versions of these
documents should have.

I hope I'm wrong, but would feel a lot better if the WG's
mailing list delivered a posting that started "I have carefully
read all the way through draft-ietf-emailcore-rfc5321bis-08
and..."

Just my opinion of course but I am at the point where I almost
wish the co-chairs would treat starting this type of thread or
responding to it as disruptive.

   john


--On Saturday, January 15, 2022 15:17 +0100 Steffen Nurpmeso
<steffen@sdaoden.eu> wrote:

> Hello.
> 
> Sorry for the late reply, i wanted to read the draft first.
> (The thread continued on ietf-smtp@ due to request.) 



From nobody Wed Jan 19 03:55:03 2022
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Subject: [Emailcore] Agenda for the EMAILCORE interim this Friday (January 21st)
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Dear WG participants,

EMAILCORE chairs are hoping to see you attending our next interim this 
Friday, at 5pm UTC.

Below is our proposed agenda with some comments:

> #17 (Deprecated Source Routes)
> https://trac.ietf.org/trac/emailcore/ticket/17
John did a good job cleaning this up. There are only some minor 
questions remaining about strength of some requirements in the new 
Appendix F.2.

Please review the new Appendix F.2 and be ready to discuss:

https://datatracker.ietf.org/doc/html/draft-ietf-emailcore-rfc5321bis-08#appendix-F.2

>
> #9 (G.7.3. Definition of domain name in Section 2.3.5)
> https://trac.ietf.org/trac/emailcore/ticket/9
Again, I believe John made some good cleanup of this text, but there are 
a couple of minor remaining issues related to text about alises (moved 
from Section 5) and whether DNS resolvability need to be mentioned in 
Section 2.3.5
>
> #4 (Exploders seem to be prohibited from adding List-* header fields)
> https://trac.ietf.org/trac/emailcore/ticket/4
We started discussing this at the last interim, but didn't have enough 
time to make progress on this. I am hoping we can resolve this one.
>
> #1 (G.1 IP address literals in EHLO)
> https://trac.ietf.org/trac/emailcore/ticket/1
>
> #47 (Accepting Messages based on EHLO Argument)
> https://trac.ietf.org/trac/emailcore/ticket/47
The above 2 tickets were addressed in rfc5321bis, but some text in the 
Applicability Statement needs confirmation/closure.
>
> #54 (G.7.17 Hop-by-hop Authentication and/or Encryption)
> https://trac.ietf.org/trac/emailcore/ticket/54
This ticket is now about text in the Applicability Statement. Todd will 
post a separate message on this.
> #16 (Review Timeout Specifications)
> https://trac.ietf.org/trac/emailcore/ticket/16
Trying to get closure on the old ticket. This is about new text proposed 
for the Applicability Statement. Todd will post a separate message on this.
> #12 (G.7.5. Improve description/definition of mailing lists, aliases, 
> and forwarding)
> https://trac.ietf.org/trac/emailcore/ticket/12
>
> #3 (G.3. Meaning of "MTA" and Related Terminolog)
> https://trac.ietf.org/trac/emailcore/ticket/3
Discussion about these started at the last interim meeting, but we 
didn't have time to make significant progress on these. Hopefully we can 
progress these tickets further this time.

Best Regards,

Alexey


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Subject: [Emailcore] Ticket #54 - Proposed Text for Applicability Statement
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--000000000000066e2805d5ef7b37
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Greetings.

Alexey mentioned in a separate message that I would be posting proposed
text for the subject ticket. This is that posting.

The ticket is ticket number 54 -
https://trac.ietf.org/trac/emailcore/ticket/54

The ticket description reads:

Should this document discuss hop-by-hop authentication or, for that
matter, encryption?


and there is a suggestion that such discussion be done in the Applicability
Statement.

Here is an initial proposal for text for the Applicability Statement to
discuss these topics.

=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D cut here=
 =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D

5. Hop-by-hop Authentication and Its Implications

Two protocols exist to allow for authentication of different identities
associated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A
third protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for
validation of the domain in the visible From header, and a fourth, ARC
[RFC8617], provides a way for each hop to record results of authentication
checks performed at that hop.

All of these are outside the scope of this document, but users and
implementers of SMTP should be aware of them and most critically of the
fact that both SPF and DKIM verification checks can produce different
results when a message transits multiple hops vice when it goes directly
from the sender to the destination, specifically =E2=80=9CFAIL=E2=80=9D res=
ults. These
unanticipated failures can and do affect DMARC verification results on some
messages, and so domain owners should be aware of this when setting DMARC
policy for their domains. As for message receivers, the ARC protocol is one
attempt to provide evidence of the results of previous authentication
checks, and it=E2=80=99s up to the receiver to decide if they trust the res=
ults and
how those results might impact message handling at their site.

6. Message Encryption and Its Implications

The default method for transmitting text using the SMTP protocol is to do
so =E2=80=9Cin the clear=E2=80=9D. Years of operational experience have sho=
wn that such
transmission exposes the message to easy compromise. To mitigate this risk,
solutions have been developed to encrypt the message in transit, either
just between servers or through the entire path from sender to message
store. This section will touch on these methods and the implications of
their use.

6.1 Opportunistic Encryption

The most common implementation of message encryption is what=E2=80=99s know=
n as
=E2=80=9Copportunistic encryption=E2=80=9D. With this method, an SMTP serve=
r announces in
its greeting that it is capable of supporting TLS encryption through the
presence of the =E2=80=9CSTARTTLS=E2=80=9D keyword. The SMTP client then at=
tempts to
negotiate an encrypted connection, and if successful, transmits the message
in encrypted form; there is no guarantee that the message will be stored in
encrypted fashion at its destination, and in fact, storage in plain text
should be expected. If negotiation fails, the client falls back to sending
the message in clear text.

Most modern implementations of SMTP support this method, and so the vast
majority of email traffic is encrypted during its time transiting from the
client to the server.

6.2 Required Encryption

Two protocols exist that move server-to-server encryption beyond =E2=80=9Cn=
ice to
have=E2=80=9D to =E2=80=9Crequired=E2=80=9D - MTA-STS [RFC8461] and DANE fo=
r SMTP [RFC7672]. While
they differ in their implementation details, SMTP servers relying on either
protocol are stating that they only accept mail if the transmission is
encrypted with TLS, and a failure to negotiate a secure connection MUST
result in the SMTP client refusing to transmit the message. Support for
both protocols is widening, but is not yet mandatory.

6.3 Personal Encryption

The more sophisticated among the end users of SMTP may take advantage of
various third party solutions that are designed to encrypt their message
immediately upon leaving the MUA, and to do so in such a way that only the
individual message recipient(s) can decrypt the message. The solutions are
too numerous to list here, and debugging any issues that may arise in
message transmission is likely to be beyond the scope of any MTA
administrator=E2=80=99s work, but they=E2=80=99re nonetheless mentioned her=
e for the sake
of completeness.

=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D cut here=
 =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D

Please discuss...

--=20

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
*m:* 703.220.4153

This email and all data transmitted with it contains confidential and/or
proprietary information intended solely for the use of individual(s)
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and may be unlawful. Please immediately notify the sender by replying to
this email and then delete it from your system.

--000000000000066e2805d5ef7b37
Content-Type: text/html; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

<div dir=3D"ltr"><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
ans-serif">Greetings.<br></div><div class=3D"gmail_default" style=3D"font-f=
amily:tahoma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"fo=
nt-family:tahoma,sans-serif">Alexey mentioned in a separate message that I =
would be posting proposed text for the subject ticket. This is that posting=
.<br clear=3D"all"></div><div class=3D"gmail_default" style=3D"font-family:=
tahoma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-fam=
ily:tahoma,sans-serif">The ticket is ticket number 54 -=C2=A0<a href=3D"htt=
ps://trac.ietf.org/trac/emailcore/ticket/54">https://trac.ietf.org/trac/ema=
ilcore/ticket/54</a></div><div class=3D"gmail_default" style=3D"font-family=
:tahoma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-fa=
mily:tahoma,sans-serif">The ticket description reads:</div><div class=3D"gm=
ail_default" style=3D"font-family:tahoma,sans-serif"><br></div><blockquote =
style=3D"margin:0 0 0 40px;border:none;padding:0px"><div class=3D"gmail_def=
ault" style=3D"font-family:tahoma,sans-serif"><span style=3D"color:rgb(0,0,=
0);font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans=
-serif;font-size:13px;background-color:rgb(255,255,255)">Should this docume=
nt discuss hop-by-hop authentication or, for that</span></div><div class=3D=
"gmail_default" style=3D"font-family:tahoma,sans-serif"><span style=3D"colo=
r:rgb(0,0,0);font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helv=
etica,sans-serif;font-size:13px;background-color:rgb(255,255,255)">matter, =
encryption?</span></div></blockquote><div><br></div><div><div class=3D"gmai=
l_default" style=3D"font-family:tahoma,sans-serif">and there is a suggestio=
n that such discussion be done in the Applicability Statement.=C2=A0</div><=
div class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><br></d=
iv><div class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif">Her=
e is an initial proposal for text for the Applicability Statement to discus=
s these topics.</div><div class=3D"gmail_default" style=3D"font-family:taho=
ma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-family:=
tahoma,sans-serif">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D</div><div class=3D"gmail_default" style=3D"f=
ont-family:tahoma,sans-serif"><br></div><font face=3D"tahoma, sans-serif"><=
span id=3D"gmail-docs-internal-guid-116a1b75-7fff-2f51-530f-dee9191a3347"><=
p dir=3D"ltr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt">=
<span style=3D"color:rgb(89,89,89);background-color:transparent;font-weight=
:700;font-variant-numeric:normal;font-variant-east-asian:normal;vertical-al=
ign:baseline;white-space:pre-wrap">5. Hop-by-hop Authentication and Its Imp=
lications </span></p><p dir=3D"ltr" style=3D"line-height:1.38;margin-top:0p=
t;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);background-color:t=
ransparent;font-variant-numeric:normal;font-variant-east-asian:normal;verti=
cal-align:baseline;white-space:pre-wrap">Two protocols exist to allow for a=
uthentication of different identities associated with an email message - SP=
F [RFC7208] and DKIM [RFC6376]. A third protocol, DMARC [RFC7489], relies o=
n SPF and DKIM to allow for validation of the domain in the visible From he=
ader, and a fourth, ARC [RFC8617], provides a way for each hop to record re=
sults of authentication checks performed at that hop.</span></p><p dir=3D"l=
tr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span styl=
e=3D"color:rgb(89,89,89);background-color:transparent;font-variant-numeric:=
normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:p=
re-wrap">All of these are outside the scope of this document, but users and=
 implementers of SMTP should be aware of them and most critically of the fa=
ct that both SPF and DKIM verification checks can produce different results=
 when a message transits multiple hops vice when it goes directly from the =
sender to the destination, specifically =E2=80=9CFAIL=E2=80=9D results. The=
se unanticipated failures can and do affect DMARC verification results on s=
ome messages, and so domain owners should be aware of this when setting DMA=
RC policy for their domains. As for message receivers, the ARC protocol is =
one attempt to provide evidence of the results of previous authentication c=
hecks, and it=E2=80=99s up to the receiver to decide if they trust the resu=
lts and how those results might impact message handling at their site.</spa=
n></p></span><br class=3D"gmail-Apple-interchange-newline"><span id=3D"gmai=
l-docs-internal-guid-e85c8228-7fff-6945-4a2e-50bace6fbe07"><p dir=3D"ltr" s=
tyle=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span style=3D"=
color:rgb(89,89,89);background-color:transparent;font-weight:700;font-varia=
nt-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;wh=
ite-space:pre-wrap">6. Message Encryption and Its Implications </span></p><=
p dir=3D"ltr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt">=
<span style=3D"color:rgb(89,89,89);background-color:transparent;font-varian=
t-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;whi=
te-space:pre-wrap">The default method for transmitting text using the SMTP =
protocol is to do so =E2=80=9Cin the clear=E2=80=9D. Years of operational e=
xperience have shown that such transmission exposes the message to easy com=
promise. To mitigate this risk, solutions have been developed to encrypt th=
e message in transit, either just between servers or through the entire pat=
h from sender to message store. This section will touch on these methods an=
d the implications of their use.</span></p></span><br class=3D"gmail-Apple-=
interchange-newline"><span id=3D"gmail-docs-internal-guid-93907b14-7fff-9fc=
5-3d18-685094946a2a"><p dir=3D"ltr" style=3D"line-height:1.38;margin-top:0p=
t;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);background-color:t=
ransparent;font-weight:700;font-variant-numeric:normal;font-variant-east-as=
ian:normal;vertical-align:baseline;white-space:pre-wrap">6.1 Opportunistic =
Encryption </span></p><p dir=3D"ltr" style=3D"line-height:1.38;margin-top:0=
pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);background-color:=
transparent;font-variant-numeric:normal;font-variant-east-asian:normal;vert=
ical-align:baseline;white-space:pre-wrap">The most common implementation of=
 message encryption is what=E2=80=99s known as =E2=80=9Copportunistic encry=
ption=E2=80=9D. With this method, an SMTP server announces in its greeting =
that it is capable of supporting TLS encryption through the presence of the=
 =E2=80=9CSTARTTLS=E2=80=9D keyword. The SMTP client then attempts to negot=
iate an encrypted connection, and if successful, transmits the message in e=
ncrypted form; there is no guarantee that the message will be stored in enc=
rypted fashion at its destination, and in fact, storage in plain text shoul=
d be expected. If negotiation fails, the client falls back to sending the m=
essage in clear text.</span></p><p dir=3D"ltr" style=3D"line-height:1.38;ma=
rgin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);backgro=
und-color:transparent;font-variant-numeric:normal;font-variant-east-asian:n=
ormal;vertical-align:baseline;white-space:pre-wrap">Most modern implementat=
ions of SMTP support this method, and so the vast majority of email traffic=
 is encrypted during its time transiting from the client to the server.</sp=
an></p></span><br class=3D"gmail-Apple-interchange-newline"><span id=3D"gma=
il-docs-internal-guid-131f5d67-7fff-cb0d-49e8-4bd5a63b4ff0"><p dir=3D"ltr" =
style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span style=3D=
"color:rgb(89,89,89);background-color:transparent;font-weight:700;font-vari=
ant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;w=
hite-space:pre-wrap">6.2 Required Encryption </span></p><p dir=3D"ltr" styl=
e=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span style=3D"col=
or:rgb(89,89,89);background-color:transparent;font-variant-numeric:normal;f=
ont-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"=
>Two protocols exist that move server-to-server encryption beyond =E2=80=9C=
nice to have=E2=80=9D to =E2=80=9Crequired=E2=80=9D - MTA-STS [RFC8461] and=
 DANE for SMTP [RFC7672]. While they differ in their implementation details=
, SMTP servers relying on either protocol are stating that they only accept=
 mail if the transmission is encrypted with TLS, and a failure to negotiate=
 a secure connection MUST result in the SMTP client refusing to transmit th=
e message. Support for both protocols is widening, but is not yet mandatory=
.</span></p></span><br class=3D"gmail-Apple-interchange-newline"><span id=
=3D"gmail-docs-internal-guid-5c876b70-7fff-fa56-8b38-af381573e997"><p dir=
=3D"ltr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span=
 style=3D"color:rgb(89,89,89);background-color:transparent;font-weight:700;=
font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:b=
aseline;white-space:pre-wrap">6.3 Personal Encryption </span></p><p dir=3D"=
ltr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><span sty=
le=3D"color:rgb(89,89,89);background-color:transparent;font-variant-numeric=
:normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:=
pre-wrap">The more sophisticated among the end users of SMTP may take advan=
tage of various third party solutions that are designed to encrypt their me=
ssage immediately upon leaving the MUA, and to do so in such a way that onl=
y the individual message recipient(s) can decrypt the message. The solution=
s are too numerous to list here, and debugging any issues that may arise in=
 message transmission is likely to be beyond the scope of any MTA administr=
ator=E2=80=99s work, but they=E2=80=99re nonetheless mentioned here for the=
 sake of completeness.</span></p></span></font><br class=3D"gmail-Apple-int=
erchange-newline"><div class=3D"gmail_default" style=3D"font-family:tahoma,=
sans-serif">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D</div><div class=3D"gmail_default" style=3D"font-famil=
y:tahoma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-f=
amily:tahoma,sans-serif">Please discuss...</div><br></div>-- <br><div dir=
=3D"ltr" class=3D"gmail_signature" data-smartmail=3D"gmail_signature"><span=
><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:0pt=
"></p><div style=3D"text-align:left"><span style=3D"vertical-align:baseline=
;white-space:pre-wrap;font-size:small;font-family:Arial"><b>Todd Herr </b><=
/span><b></b><span style=3D"font-family:Arial;font-size:small;white-space:p=
re-wrap"> | Technical Director, Standards and Ecosystem</span></div><span s=
tyle=3D"vertical-align:baseline;white-space:pre-wrap;font-size:small;font-f=
amily:Arial"><div style=3D"text-align:left"><span style=3D"vertical-align:b=
aseline"><b>e:</b></span><span style=3D"vertical-align:baseline"> <a href=
=3D"mailto:todd.herr@valimail.com" target=3D"_blank">todd.herr@valimail.com=
</a> </span></div></span><span><div><span><b>m:</b></span><span> 703.220.41=
53</span><span></span></div><div style=3D"text-align:left"><img style=3D"wi=
dth:175px;height:43px" src=3D"https://hosted-packages.s3-us-west-1.amazonaw=
s.com/Valimail+Logo.png"></div></span><p dir=3D"ltr" style=3D"background-co=
lor:rgb(255,255,255);line-height:1.38;margin-top:0pt;margin-bottom:0pt"><fo=
nt face=3D"Arial" color=3D"#666666"><span style=3D"font-size:10.6667px;whit=
e-space:pre-wrap">This email and all data transmitted with it contains conf=
idential and/or proprietary information intended solely for the use of indi=
vidual(s) authorized to receive it. If you are not an intended and authoriz=
ed recipient you are hereby notified of any use, disclosure, copying or dis=
tribution of the information included in this transmission is prohibited an=
d may be unlawful. Please immediately notify the sender by replying to this=
 email and then delete it from your system.</span></font></p></span></div><=
/div>

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Subject: [Emailcore] Ticket #16 - Proposed Text for Applicability Statement
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--000000000000b195a205d5ef8d8f
Content-Type: text/plain; charset="UTF-8"

Greetings.

Alexey mentioned in a separate message that I would be posting proposed
text for the subject ticket. This is that posting.

The ticket is ticket number 16 -
https://trac.ietf.org/trac/emailcore/ticket/16 - and the topic is the
timeout specifications in RFC 5321, specifically whether or not they might
be too generous.

Discussion at IETF 110 (https://codimd.ietf.org/notes-ietf-110-emailcore)
seemed to land on "Leave 5321 alone, but maybe add something to the
Applicability Statement"

Here is the initial proposed text for something to add to the Applicability
Statement.

===================== cut here ========================

7. Timeout Specifications

The current SMTP specification (5321bis), as well as the two before it
(RFC5321 and RFC2821) contain recommendations for minimum timeout values
for various operations. Given the age of RFC 2821 (published in April 2001)
and advances in networking and computing technology since then, it might
seem that these timeout values are far too generous. However, those same
advances have been relied on by MTA implementers to add more features and
functionality to SMTP transactions.

The recommended minimum timeouts are specified as SHOULD, not MUST, and so
implementers may choose to use shorter timeouts if operational needs or
experience indicate that to be appropriate.
===================== cut here ========================

Please discuss...

-- 

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
*m:* 703.220.4153

This email and all data transmitted with it contains confidential and/or
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<div dir=3D"ltr"><div class=3D"gmail_default" style=3D""><div class=3D"gmai=
l_default" style=3D"font-family:tahoma,sans-serif">Greetings.<br></div><div=
 class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><br></div>=
<div class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif">Alexey=
 mentioned in a separate message that I would be posting proposed text for =
the subject ticket. This is that posting.<br clear=3D"all"></div><div class=
=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><br></div><div c=
lass=3D"gmail_default" style=3D"font-family:tahoma,sans-serif">The ticket i=
s ticket number=C2=A016 -=C2=A0<a href=3D"https://trac.ietf.org/trac/emailc=
ore/ticket/16">https://trac.ietf.org/trac/emailcore/ticket/16</a> - and the=
 topic is the timeout specifications in RFC 5321, specifically=C2=A0whether=
 or not they might be too generous.</div><div class=3D"gmail_default" style=
=3D"font-family:tahoma,sans-serif"><br></div><div class=3D"gmail_default" s=
tyle=3D"font-family:tahoma,sans-serif"><span style=3D"color:rgb(0,0,0);font=
-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans-serif;=
font-size:13px">Discussion at IETF 110 (</span><a class=3D"ext-link" href=
=3D"https://codimd.ietf.org/notes-ietf-110-emailcore" style=3D"text-decorat=
ion-line:none;color:rgb(187,0,0);border-bottom:1px dotted rgb(187,187,187);=
font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans-se=
rif;font-size:13px"><span class=3D"gmail-icon" style=3D"background:url(&quo=
t;../extlink.gif&quot;) 0% 50% no-repeat;padding-left:15px"></span>https://=
codimd.ietf.org/notes-ietf-110-emailcore</a><span style=3D"color:rgb(0,0,0)=
;font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans-s=
erif;font-size:13px">) seemed to land on &quot;Leave 5321 alone, but maybe =
add something to the Applicability Statement&quot;</span><br></div><div cla=
ss=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><span style=3D=
"color:rgb(0,0,0);font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;=
,Helvetica,sans-serif;font-size:13px"><br></span></div><div class=3D"gmail_=
default" style=3D"font-family:tahoma,sans-serif"><span style=3D"color:rgb(0=
,0,0);font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,s=
ans-serif;font-size:13px">Here is the initial proposed text for something t=
o add to the Applicability Statement.</span></div><div class=3D"gmail_defau=
lt" style=3D"font-family:tahoma,sans-serif"><span style=3D"color:rgb(0,0,0)=
;font-family:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans-s=
erif;font-size:13px"><br></span></div><div class=3D"gmail_default" style=3D=
"font-family:tahoma,sans-serif"><span style=3D"color:rgb(0,0,0);font-family=
:Verdana,Arial,&quot;Bitstream Vera Sans&quot;,Helvetica,sans-serif;font-si=
ze:13px">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D cu=
t here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D</span></div><div class=3D"gmail_default" style=3D""><span id=3D"gmai=
l-docs-internal-guid-78b379fe-7fff-c1ff-8988-4136012ef750" style=3D""><p di=
r=3D"ltr" style=3D"line-height:1.38;margin-top:0pt;margin-bottom:12pt"><spa=
n style=3D"color:rgb(89,89,89);background-color:transparent;font-weight:700=
;font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:=
baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif" style=3D""=
>7. Timeout Specifications</font></span></p><p dir=3D"ltr" style=3D"line-he=
ight:1.38;margin-top:0pt;margin-bottom:12pt"><font face=3D"tahoma, sans-ser=
if"><span style=3D"color:rgb(89,89,89);background-color:transparent;font-va=
riant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline=
;white-space:pre-wrap">The current SMTP specification (5321bis), as well as=
 the two before it (RFC5321 and RFC2821) contain recommendations for minimu=
m timeout values for various operations. Given the age of RFC 2821 (publish=
ed in April 2001) and advances in networking and computing technology since=
 then, it might seem that these timeout values are far too generous. Howeve=
r, those same advances have been relied on by MTA implementers to add more =
features and functionality to SMTP transactions.</span><span style=3D"color=
:rgb(89,89,89);background-color:transparent;font-variant-numeric:normal;fon=
t-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"><=
br></span><span style=3D"color:rgb(89,89,89);background-color:transparent;f=
ont-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:ba=
seline;white-space:pre-wrap"><br></span><span style=3D"color:rgb(89,89,89);=
background-color:transparent;font-variant-numeric:normal;font-variant-east-=
asian:normal;vertical-align:baseline;white-space:pre-wrap">The recommended =
minimum timeouts are specified as SHOULD, not MUST, and so implementers may=
 choose to use shorter timeouts if operational needs or experience indicate=
 that to be appropriate.</span></font></p></span></div><div class=3D"gmail_=
default" style=3D"font-family:tahoma,sans-serif"><div class=3D"gmail_defaul=
t"><span style=3D"color:rgb(0,0,0);font-family:Verdana,Arial,&quot;Bitstrea=
m Vera Sans&quot;,Helvetica,sans-serif;font-size:13px">=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D cut here =3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D</span></div><br clas=
s=3D"gmail-Apple-interchange-newline"></div><div class=3D"gmail_default" st=
yle=3D"font-family:tahoma,sans-serif">Please discuss...</div></div><div><br=
></div>-- <br><div dir=3D"ltr" class=3D"gmail_signature" data-smartmail=3D"=
gmail_signature"><span><p dir=3D"ltr" style=3D"line-height:1.656;margin-top=
:0pt;margin-bottom:0pt"></p><div style=3D"text-align:left"><span style=3D"v=
ertical-align:baseline;white-space:pre-wrap;font-size:small;font-family:Ari=
al"><b>Todd Herr </b></span><b></b><span style=3D"font-family:Arial;font-si=
ze:small;white-space:pre-wrap"> | Technical Director, Standards and Ecosyst=
em</span></div><span style=3D"vertical-align:baseline;white-space:pre-wrap;=
font-size:small;font-family:Arial"><div style=3D"text-align:left"><span sty=
le=3D"vertical-align:baseline"><b>e:</b></span><span style=3D"vertical-alig=
n:baseline"> <a href=3D"mailto:todd.herr@valimail.com" target=3D"_blank">to=
dd.herr@valimail.com</a> </span></div></span><span><div><span><b>m:</b></sp=
an><span> 703.220.4153</span><span></span></div><div style=3D"text-align:le=
ft"><img style=3D"width:175px;height:43px" src=3D"https://hosted-packages.s=
3-us-west-1.amazonaws.com/Valimail+Logo.png"></div></span><p dir=3D"ltr" st=
yle=3D"background-color:rgb(255,255,255);line-height:1.38;margin-top:0pt;ma=
rgin-bottom:0pt"><font face=3D"Arial" color=3D"#666666"><span style=3D"font=
-size:10.6667px;white-space:pre-wrap">This email and all data transmitted w=
ith it contains confidential and/or proprietary information intended solely=
 for the use of individual(s) authorized to receive it. If you are not an i=
ntended and authorized recipient you are hereby notified of any use, disclo=
sure, copying or distribution of the information included in this transmiss=
ion is prohibited and may be unlawful. Please immediately notify the sender=
 by replying to this email and then delete it from your system.</span></fon=
t></p></span></div></div>

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From: "John Levine" <johnl@taugh.com>
To: emailcore@ietf.org
Cc: todd.herr@valimail.com
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Subject: Re: [Emailcore] Ticket #54 - Proposed Text for Applicability Statement
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It appears that Todd Herr  <todd.herr@valimail.com> said:
>-=-=-=-=-=-
>
>Greetings.
>
>Alexey mentioned in a separate message that I would be posting proposed
>text for the subject ticket. This is that posting.
>
>The ticket is ticket number 54 -
>https://trac.ietf.org/trac/emailcore/ticket/54
>
>The ticket description reads:
>
>Should this document discuss hop-by-hop authentication or, for that
>matter, encryption?

DKIM and DMARC are end to end, SPF is hop by hop, but when I think of hop-by-hop
authentication and encryption, I think of mta-sts and STARTTLS.

R's,
John


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Date: Wed, 19 Jan 2022 11:02:14 -0500
From: Hector Santos <hsantos@isdg.net>
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Subject: Re: [Emailcore] Ticket #16 - Proposed Text for Applicability Statement
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On 1/19/2022 8:41 AM, Todd Herr wrote:
> ===================== cut here ========================
>
> 7. Timeout Specifications
>
> The current SMTP specification (5321bis), as well as the two before 
> it (RFC5321 and RFC2821) contain recommendations for minimum timeout 
> values for various operations. Given the age of RFC 2821 (published 
> in April 2001) and advances in networking and computing technology 
> since then, it might seem that these timeout values are far too 
> generous. However, those same advances have been relied on by MTA 
> implementers to add more features and functionality to SMTP 
> transactions.
>
> The recommended minimum timeouts are specified as SHOULD, not MUST, 
> and so implementers may choose to use shorter timeouts if 
> operational needs or experience indicate that to be appropriate.
>
> ===================== cut here ========================
>
> Please discuss...
>

+1. I believe this is closer to modern receiver behavior (SHOULD use, 
may reduce).  With senders, I don't believe we have reduced the 
timeouts - only on the server side are the options available (to 
revert back to std).  I like the text you have but I would also 
consider the sender is a MUST to be protocol correct with "standard" 
receiver logic.

MTA  MUST use but be aware of MDA, MSA. ALWAYS be ready for drops no 
matter what.
MDA SHOULD use, may reduce.
MSA  SHOULD use, may reduce.

Thanks



-- 
Hector Santos,
https://secure.santronics.com
https://twitter.com/hectorsantos




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It appears that John C Klensin  <john-ietf@jck.com> said:
>I would not feel so strongly about this except that, with a
>grand total of zero comments on the changes and questions raised
>in draft-ietf-emailcore-rfc5321bis-08 since it was posted two
>weeks ago, ...

FWIW, I've been going through the draft and so far haven't found anything
that I'd want to change.

In this case (albeit not in general I realize) silence actually does mean consent.

R's,
John


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--On Thursday, January 20, 2022 23:32 -0500 John Levine
<johnl@taugh.com> wrote:

> It appears that John C Klensin  <john-ietf@jck.com> said:
>> I would not feel so strongly about this except that, with a
>> grand total of zero comments on the changes and questions
>> raised in draft-ietf-emailcore-rfc5321bis-08 since it was
>> posted two weeks ago, ...
> 
> FWIW, I've been going through the draft and so far haven't
> found anything that I'd want to change.
> 
> In this case (albeit not in general I realize) silence
> actually does mean consent.

John,

The effort and calibration are very much appreciated.  And I
appreciate your speaking up.

Talk with you (and I hope everyone else) tomorrow.  

For everyone else, and with a bit under twelve hours to go
before the interim, I'd strongly encourage people to take a
careful look at Section 2.3.5 and Section 5.  I've moved some
material between the two sections and done some rewriting but
concluded I need feedback from the WG before either stopping or
going further, remembering that such rewrites risk introducing
errors.  Those two sections are on the agenda, but doubt that it
is possible to understand enough about what is going on by
looking at them in real time during the meeting.

thanks,
   john


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On 1/19/2022 3:54 AM, Alexey Melnikov wrote:
> #9 (G.7.3. Definition of domain name in Section 2.3.5)
> https://trac.ietf.org/trac/emailcore/ticket/9



Using this section *merely as an example*, I'd like to (re-)raise a 
question about criteria for this version of the document.

For reference, the charter's guidance is:

> This working group will conduct a limited review and revision to the base
> email specifications, and will publish new versions of these documents at
> Internet Standard status, per RFC 6410. The limited review is restricted
> to corrections and clarifications only, with a strong emphasis on keeping
> these minimal and avoiding broader changes to terminology or document
> organization. In addition to processing existing, verified errata and
> errata marked as "held for document update", the WG may address
> newly-offered errata. However, no new protocol extensions or amendments
> will be considered for inclusion into 5321bis and 5322bis documents,
> unless they are already published as IETF Stream RFCs and are at
> sufficient maturity level to move to Internet Standard.


"corrections and clarifications"

"no new protocol extensions or amendments...unless they are already 
published as IETF Stream RFCs and are at sufficient maturity level to 
move to Internet Standard."



The Domain Name System is separate from email and now has extensive 
documentation of specs and use. This was not true in 1982, when SMTP and 
the DNS were in parallel development.

The SMTP specification has no authority of any aspect of the DNS -- 
except SMTP's /use/ of it.

Therefore, any text in the SMTP specification that provides 
specification of DNS syntax or semantics is, at best, wholly redundant 
with the authoritative specification(s).  The 'at best' is because 
redundant specification always invites /divergent/ specification.

   *  This raises the question of why the current effort seeks to modify
      text that does specify Domain Name syntax or semantics, rather than
      simply having the document cite authoritative sources?

A concern that it regularly raised about such a change to this document 
is that it might disrupt existing use of SMTP.  I suggest that if that 
were a real danger, it would mean that there is use of the DNS in SMTP 
that does not conform to the authoritative DNS documents.  I'd be quite 
surprised to see any support for actual non-conformance.  Hence the fear 
has a logic that is presumably not matched by practice.



Scope:

Another distinction for the current work is normative specification vs. 
pedagogy and commentary.

   *  Obviously, the current effort /must/ repair any normative errors in
      the SMTP protocol specification.

   *  Presumably it also should improve on SMTP protocol pedagogy or
      commentary that is now known to be incorrect.

   *  What is not at all clear is why the current document should include
      commentary or guidance about anything over which it has no
      normative control and is, again, likely to be incomplete and/or
      divergent from documents that do have normative control?


d/
-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


From nobody Fri Jan 21 20:17:45 2022
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Date: Fri, 21 Jan 2022 23:17:28 -0500
From: John C Klensin <john-ietf@jck.com>
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Hi.

During Friday's interim meeting, a decision was made (associated
with Ticket #4) to drop the last sentence of the first paragraph
of Section 3.4.2, which reads (in -08):

	'However, in this case, the message header section (RFC
	5322 [12]) MUST be left unchanged; in particular, the
	"From" field of the header section is unaffected.'

Checking back over my notes, that sentence appeared in RFC 2821.
Checking further, the decision in DRUMS to put it in was
apparently based on real-world confusion as to whether a change
in the reverse-path was required to be reflected in the mail
headers.  

So, IMO, we should remove that text iff people are convinced
that potential for confusion has vanished in the last 20 years.
Otherwise, it should be retained in some form.

So this is a request for mailing list discussion on that
specific topic before I take the conclusion of the Interim as
definitive and change the text.

thanks,
   john


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From: "John Levine" <johnl@taugh.com>
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Subject: Re: [Emailcore] Post-Interim question about Section 3.4.2 of draft-ietf-emailcore-rfc5321bis-08
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It appears that John C Klensin  <john-ietf@jck.com> said:
>Hi.
>
>During Friday's interim meeting, a decision was made (associated
>with Ticket #4) to drop the last sentence of the first paragraph
>of Section 3.4.2, which reads (in -08):
>
>	'However, in this case, the message header section (RFC
>	5322 [12]) MUST be left unchanged; in particular, the
>	"From" field of the header section is unaffected.'
>
>Checking back over my notes, that sentence appeared in RFC 2821.
>Checking further, the decision in DRUMS to put it in was
>apparently based on real-world confusion as to whether a change
>in the reverse-path was required to be reflected in the mail
>headers.  

If people still think that the bounce address has to match the From header,
we've got worse problems than this sentence.

For the list-id issue, I suppose we could say that existing message headers
are left unchanged, implying that if you want to add new ones, you can.

R's,
John


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From: John C Klensin <john-ietf@jck.com>
To: John Levine <johnl@taugh.com>, emailcore@ietf.org
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Subject: Re: [Emailcore] Post-Interim question about Section 3.4.2 of draft-ietf-emailcore-rfc5321bis-08
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--On Friday, January 21, 2022 23:29 -0500 John Levine
<johnl@taugh.com> wrote:

> It appears that John C Klensin  <john-ietf@jck.com> said:
>> Hi.
>> 
>> During Friday's interim meeting, a decision was made
>> (associated with Ticket #4) to drop the last sentence of the
>> first paragraph of Section 3.4.2, which reads (in -08):
>> 
>>	'However, in this case, the message header section (RFC
>>	5322 [12]) MUST be left unchanged; in particular, the
>>	"From" field of the header section is unaffected.'
>> 
>> Checking back over my notes, that sentence appeared in RFC
>> 2821. Checking further, the decision in DRUMS to put it in was
>> apparently based on real-world confusion as to whether a
>> change in the reverse-path was required to be reflected in
>> the mail headers.  
> 
> If people still think that the bounce address has to match the
> From header, we've got worse problems than this sentence.

Agreed.  But I think we have worse problems than that sentence
even without that condition, so I am trying to be careful and
ask.

> For the list-id issue, I suppose we could say that existing
> message headers are left unchanged, implying that if you want
> to add new ones, you can.

That was the case I was concerned about and (as an individual) I
like your suggestion for how to handle it.  

Others?
   thanks,
     john



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>> For the list-id issue, I suppose we could say that existing
>> message headers are left unchanged, implying that if you want
>> to add new ones, you can.
>
> That was the case I was concerned about and (as an individual) I
> like your suggestion for how to handle it.

As a general rule, it seems to me that if you're rewriting headers, you're 
doing submission, which is fine but it's not SMTP.

We might put something in the A/S along the lines of the point of the 
bounce address is send failure notifications to someone who can do 
something about it.  When an MTA changes the destination address, 
the decision whether to change the bounce address is an administrative 
one, not a technical one, to get the bounces to the appropriate party,

Regards,
John Levine, johnl@taugh.com, Taughannock Networks, Trumansburg NY
Please consider the environment before reading this e-mail. https://jl.ly


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> As a general rule, it seems to me that if you're rewriting headers, 
> you're doing submission, which is fine but it's not SMTP.
> 
> We might put something in the A/S along the lines of the point of the 
> bounce address is send failure notifications to someone who can do 
> something about it.  When an MTA changes the destination address, the 
> decision whether to change the bounce address is an administrative one, 
> not a technical one, to get the bounces to the appropriate party,


+1

This probably aids the distinction between 'protocol spec' and 'service 
spec', where a service is one or more protocols and the relevant 
operational guidance.  An A/S seems more in line with a role as service 
specification.  Yes?

SMTP is only a component of an email service.  So it is problematic to 
have it give guidance about activities beyond its scope.  (That the 
protocol/service conflation dates back to RFC 821 doesn't change the 
nature of the issue, just makes its genesis more understandable and, 
arguably, excusable.


d/
-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


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A new meeting session request has just been submitted by Alexey Melnikov, a Chair of the emailcore working group.


---------------------------------------------------------
Working Group Name: Revision of core Email specifications
Area Name: Applications and Real-Time Area
Session Requester: Alexey Melnikov


Number of Sessions: 1
Length of Session(s): 1 Hour
Number of Attendees: 50
Conflicts to Avoid: 
 Chair conflict: extra jmap dmarc uta cfrg
 Technology overlap: calext dispatch secdispatch
 Key participant conflict: gendispatch wpack

       
 Can't meet: Monday morning, Monday early afternoon, Tuesday morning, Tuesday early afternoon, Wednesday morning, Wednesday early afternoon, Thursday morning, Thursday early afternoon, Friday morning, Friday early afternoon

People who must be present:
  Pete Resnick
  Alexey Melnikov
  Murray Kucherawy
  Dr. John C. Klensin
  Todd Herr

Resources Requested:

Special Requests:
  Late afternoon slot on any day, if possible
---------------------------------------------------------



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From: Todd Herr <todd.herr@valimail.com>
Date: Mon, 24 Jan 2022 18:18:26 -0500
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Subject: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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--0000000000007a77a405d65c3034
Content-Type: text/plain; charset="UTF-8"

Greetings.

Thanks to all who attended the interim on January 21.

I've listened to the recording a couple of times and reviewed the notes (
https://notes.ietf.org/notes-emailcore-interim-jan-2022) in an effort to
propose better text for the subject topic. Before I really start writing,
though, I want to throw the following outline to the group to see if it's
directionally correct.

   - Define encryption (transmitting messages in ciphertext, rather than in
   the clear, to provide privacy of communication) and authentication
   (establishing the identity of the hosts involved in the transaction), both
   done using TLS.
   - Discuss opportunistic TLS (sometimes called opportunistic encryption)
   and mention that it's encryption without authentication.
   - Discuss MTA-STS and DANE for SMTP, which are both encryption with
   authentication.
   - Mention SPF, DKIM, DMARC, and ARC, which are authentication protocols,
   but not the kind of authentication we're talking about here.
   - Mention private use message encryption (e.g., PGP) but only for the
   purposes of mentioning that it's out of scope for the A/S

Appreciate your collective feedback, to include suggested text for the
definitions of encryption and authentication.

-- 

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
*m:* 703.220.4153

This email and all data transmitted with it contains confidential and/or
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and may be unlawful. Please immediately notify the sender by replying to
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--0000000000007a77a405d65c3034
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<div dir=3D"ltr"><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
ans-serif">Greetings.<br clear=3D"all"></div><div class=3D"gmail_default" s=
tyle=3D"font-family:tahoma,sans-serif"><br></div><div class=3D"gmail_defaul=
t" style=3D"font-family:tahoma,sans-serif">Thanks to all who attended the i=
nterim on January 21.</div><div class=3D"gmail_default" style=3D"font-famil=
y:tahoma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-f=
amily:tahoma,sans-serif">I&#39;ve listened to the recording a couple of tim=
es and reviewed the notes (<a href=3D"https://notes.ietf.org/notes-emailcor=
e-interim-jan-2022">https://notes.ietf.org/notes-emailcore-interim-jan-2022=
</a>) in an effort to propose better text for the subject topic. Before I r=
eally start writing, though, I want to throw the following outline to the g=
roup to see if it&#39;s directionally correct.</div><div class=3D"gmail_def=
ault" style=3D"font-family:tahoma,sans-serif"><ul><li>Define encryption (tr=
ansmitting messages in ciphertext, rather than in the clear, to provide pri=
vacy of communication) and authentication (establishing the identity of the=
 hosts involved in the transaction), both done using TLS.</li><li>Discuss o=
pportunistic TLS (sometimes called opportunistic encryption) and mention th=
at it&#39;s encryption without authentication.</li><li>Discuss MTA-STS and =
DANE for SMTP, which are both encryption=C2=A0with authentication.</li><li>=
Mention SPF, DKIM, DMARC, and ARC, which are authentication protocols, but =
not the kind of authentication we&#39;re talking about here.</li><li>Mentio=
n private use message encryption=C2=A0(e.g., PGP) but only for the purposes=
 of mentioning that it&#39;s out of scope for the A/S</li></ul><div>Appreci=
ate your collective feedback, to include suggested text for the definitions=
 of encryption and authentication.</div></div><div><br></div>-- <br><div di=
r=3D"ltr" class=3D"gmail_signature" data-smartmail=3D"gmail_signature"><spa=
n><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:0p=
t"></p><div style=3D"text-align:left"><span style=3D"vertical-align:baselin=
e;white-space:pre-wrap;font-size:small;font-family:Arial"><b>Todd Herr </b>=
</span><b></b><span style=3D"font-family:Arial;font-size:small;white-space:=
pre-wrap"> | Technical Director, Standards and Ecosystem</span></div><span =
style=3D"vertical-align:baseline;white-space:pre-wrap;font-size:small;font-=
family:Arial"><div style=3D"text-align:left"><span style=3D"vertical-align:=
baseline"><b>e:</b></span><span style=3D"vertical-align:baseline"> <a href=
=3D"mailto:todd.herr@valimail.com" target=3D"_blank">todd.herr@valimail.com=
</a> </span></div></span><span><div><span><b>m:</b></span><span> 703.220.41=
53</span><span></span></div><div style=3D"text-align:left"><img style=3D"wi=
dth:175px;height:43px" src=3D"https://hosted-packages.s3-us-west-1.amazonaw=
s.com/Valimail+Logo.png"></div></span><p dir=3D"ltr" style=3D"background-co=
lor:rgb(255,255,255);line-height:1.38;margin-top:0pt;margin-bottom:0pt"><fo=
nt face=3D"Arial" color=3D"#666666"><span style=3D"font-size:10.6667px;whit=
e-space:pre-wrap">This email and all data transmitted with it contains conf=
idential and/or proprietary information intended solely for the use of indi=
vidual(s) authorized to receive it. If you are not an intended and authoriz=
ed recipient you are hereby notified of any use, disclosure, copying or dis=
tribution of the information included in this transmission is prohibited an=
d may be unlawful. Please immediately notify the sender by replying to this=
 email and then delete it from your system.</span></font></p></span></div><=
/div>

--0000000000007a77a405d65c3034--


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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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It appears that Todd Herr  <todd.herr@valimail.com> said:
>   - Define encryption (transmitting messages in ciphertext, rather than in
>   the clear, to provide privacy of communication) and authentication
>   (establishing the identity of the hosts involved in the transaction), both
>   done using TLS.
>   - Discuss opportunistic TLS (sometimes called opportunistic encryption)
>   and mention that it's encryption without authentication.
>   - Discuss MTA-STS and DANE for SMTP, which are both encryption with
>   authentication.
>   - Mention SPF, DKIM, DMARC, and ARC, which are authentication protocols,
>   but not the kind of authentication we're talking about here.
>   - Mention private use message encryption (e.g., PGP) but only for the
>   purposes of mentioning that it's out of scope for the A/S

Seems reasonable.

>Appreciate your collective feedback, to include suggested text for the
>definitions of encryption and authentication.

You would think we would have standard text for those by now.

Since we use TLS, the encryption and authentication for mail servers is the same
as for web servers, so that might be a good place to look.

R's,
John


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From: Todd Herr <todd.herr@valimail.com>
Date: Tue, 25 Jan 2022 16:21:32 -0500
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To: emailcore@ietf.org
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Archived-At: <https://mailarchive.ietf.org/arch/msg/emailcore/489Ui--aIqT3D2JjKcpuzbu511E>
Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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--00000000000041dfa105d66eace8
Content-Type: text/plain; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

Here is my post-interim suggestion for text to use in the A/S to cover the
topics of Confidentiality and Authentication

=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D cut here
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D

5. Confidentiality and Authentication with SMTP

The default method for transmitting text using the SMTP protocol is to do
so =E2=80=9Cin the clear=E2=80=9D. Years of operational experience have sho=
wn that such
transmission exposes the message to easy compromise. To mitigate this risk,
SMTP has evolved over the years to allow for easy integration and support
of Transport Layer Security (TLS - RFC8446) to provide both confidentiality
and authentication in the transmission of messages. This section will
discuss those topics and their most common uses.

It is important that the reader understands what is meant by the terms
=E2=80=9CAuthentication=E2=80=9D and =E2=80=9CConfidentiality=E2=80=9D, and=
 for that we will borrow
directly from RFC8446.

   -

   Authentication is the process of establishing the identity of the
   endpoints (e.g., the hosts) of the SMTP transaction
   -

   The term =E2=80=9Cconfidentiality=E2=80=9D describes a state where the d=
ata (i.e., the
   message) is transmitted in a way that it is only visible to the endpoint=
s.

It is not uncommon for implementers to use the term =E2=80=9Cencryption=E2=
=80=9D to mean
=E2=80=9Cconfidentiality=E2=80=9D, but this is not quite correct. Rather, e=
ncryption using
TLS is the current method by which confidentiality is achieved with SMTP,
but that does not mean that future methods might not be developed.

5.1 Optional Confidentiality

The most common implementation of message confidentiality is what=E2=80=99s=
 known
as =E2=80=9Copportunistic TLS=E2=80=9D, which is frequently referred to as =
=E2=80=9Copportunistic
encryption=E2=80=9D. With this method, an SMTP server announces in its gree=
ting
that it is capable of supporting TLS encryption through the presence of the
=E2=80=9CSTARTTLS=E2=80=9D keyword. The SMTP client then attempts to negoti=
ate an encrypted
connection, and if successful, transmits the message in encrypted form;
there is no guarantee that the message will be stored in encrypted fashion
at its destination, and in fact, storage in plain text should be expected.
If negotiation fails, the client falls back to sending the message in clear
text.

Opportunistic TLS is confidentiality without authentication, because no
effort is made to authenticate the endpoints of the transmission, and it is
optional confidentiality due to the ability to fall back to transmission in
the clear if a secure connection cannot be established. That said, most
modern implementations of the SMTP protocol support this method, especially
at the largest mailbox providers, and so the vast majority of email traffic
is encrypted during its time transiting from the client to the server.

5.2 Required Confidentiality, with Authentication

Two protocols exist that move message confidentiality from optional to
required - MTA-STS [RFC8461] and DANE for SMTP [RFC7672]. While they differ
in their implementation details, SMTP servers relying on either protocol
are stating that they only accept mail if the transmission can be encrypted
with TLS, and a failure to negotiate a secure connection MUST result in the
SMTP client refusing to transmit the message. Support for both protocols is
widening, but is not yet mandatory.

These two protocols differ from Opportunistic TLS not only because they
require message confidentiality, but also because they require
authentication.

5.3 Message-Level Authentication

Protocols exist to allow for authentication of different identities
associated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A
third protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for
validation of the domain in the visible From header, and a fourth, ARC
[RFC8617], provides a way for each hop to record results of authentication
checks performed at that hop.

All of these are outside the scope of this document, as they are outside
the scope of the SMTP protocol. They deal with authentication of the
message, not the endpoints.

5.4 Message-Level Confidentiality

The more sophisticated among the end users of SMTP may take advantage of
various third party solutions that are designed to encrypt their message
immediately upon leaving the MUA, and to do so in such a way that only the
individual message recipient(s) can decrypt the message. The solutions
(e.g., PGP) are too numerous to list here, and as they operate at the
message level rather than the SMTP protocol level, they are out of scope
for this document.
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D cut here
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D

Have at it...


--=20

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
*m:* 703.220.4153

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proprietary information intended solely for the use of individual(s)
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recipient you are hereby notified of any use, disclosure, copying or
distribution of the information included in this transmission is prohibited
and may be unlawful. Please immediately notify the sender by replying to
this email and then delete it from your system.

--00000000000041dfa105d66eace8
Content-Type: text/html; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

<div dir=3D"ltr"><div dir=3D"ltr"><div class=3D"gmail_default" style=3D"fon=
t-family:tahoma,sans-serif">Here is my post-interim suggestion for text to =
use in the A/S to cover the topics of Confidentiality and Authentication</d=
iv><div class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><br=
></div></div><div class=3D"gmail_default" style=3D"font-family:tahoma,sans-=
serif">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D</div><div><br></div><div class=3D"gmail_quote"><div dir=3D"=
ltr" class=3D"gmail_attr"><span id=3D"gmail-docs-internal-guid-f6bbc9b3-7ff=
f-49b6-f827-7f019fb1f6f4"><p dir=3D"ltr" style=3D"line-height:1.656;margin-=
top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-weight:=
700;font-variant-numeric:normal;font-variant-east-asian:normal;vertical-ali=
gn:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif" style=
=3D"">5. Confidentiality and Authentication with SMTP</font></span></p><p d=
ir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><s=
pan style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-e=
ast-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=
=3D"tahoma, sans-serif">The default method for transmitting text using the =
SMTP protocol is to do so =E2=80=9Cin the clear=E2=80=9D. Years of operatio=
nal experience have shown that such transmission exposes the message to eas=
y compromise. To mitigate this risk, SMTP has evolved over the years to all=
ow for easy integration and support of Transport Layer Security (TLS - RFC8=
446) to provide both confidentiality and authentication in the transmission=
 of messages. This section will discuss those topics and their most common =
uses.</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top=
:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-variant-nu=
meric:normal;font-variant-east-asian:normal;vertical-align:baseline;white-s=
pace:pre-wrap"><font face=3D"tahoma, sans-serif">It is important that the r=
eader understands what is meant by the terms =E2=80=9CAuthentication=E2=80=
=9D and =E2=80=9CConfidentiality=E2=80=9D, and for that we will borrow dire=
ctly from RFC8446.</font></span></p><ul style=3D"margin-top:0px;margin-bott=
om:0px"><li dir=3D"ltr" style=3D"list-style-type:disc;color:rgb(89,89,89);b=
ackground-color:transparent;font-variant-numeric:normal;font-variant-east-a=
sian:normal;vertical-align:baseline;white-space:pre"><p dir=3D"ltr" style=
=3D"line-height:1.656;margin-top:0pt;margin-bottom:0pt" role=3D"presentatio=
n"><span style=3D"font-variant-numeric:normal;font-variant-east-asian:norma=
l;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-=
serif">Authentication is the process of establishing the identity of the en=
dpoints (e.g., the hosts) of the SMTP transaction</font></span></p></li><li=
 dir=3D"ltr" style=3D"list-style-type:disc;color:rgb(89,89,89);background-c=
olor:transparent;font-variant-numeric:normal;font-variant-east-asian:normal=
;vertical-align:baseline;white-space:pre"><p dir=3D"ltr" style=3D"line-heig=
ht:1.656;margin-top:0pt;margin-bottom:12pt" role=3D"presentation"><span sty=
le=3D"font-variant-numeric:normal;font-variant-east-asian:normal;vertical-a=
lign:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">The t=
erm =E2=80=9Cconfidentiality=E2=80=9D describes a state where the data (i.e=
., the message) is transmitted in a way that it is only visible to the endp=
oints.</font></span></p></li></ul><p dir=3D"ltr" style=3D"line-height:1.656=
;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font=
-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:basel=
ine;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">It is not uncom=
mon for implementers to use the term =E2=80=9Cencryption=E2=80=9D to mean =
=E2=80=9Cconfidentiality=E2=80=9D, but this is not quite correct. Rather, e=
ncryption using TLS is the current method by which confidentiality is achie=
ved with SMTP, but that does not mean that future methods might not be deve=
loped.</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-to=
p:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-weight:70=
0;font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align=
:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">5.1 Optio=
nal Confidentiality</font></span></p><p dir=3D"ltr" style=3D"line-height:1.=
656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);f=
ont-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:ba=
seline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">The most com=
mon implementation of message confidentiality is what=E2=80=99s known as =
=E2=80=9Copportunistic TLS=E2=80=9D, which is frequently referred to as =E2=
=80=9Copportunistic encryption=E2=80=9D. With this method, an SMTP server a=
nnounces in its greeting that it is capable of supporting TLS encryption th=
rough the presence of the =E2=80=9CSTARTTLS=E2=80=9D keyword. The SMTP clie=
nt then attempts to negotiate an encrypted connection, and if successful, t=
ransmits the message in encrypted form; there is no guarantee that the mess=
age will be stored in encrypted fashion at its destination, and in fact, st=
orage in plain text should be expected. If negotiation fails, the client fa=
lls back to sending the message in clear text.</font></span></p><p dir=3D"l=
tr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span sty=
le=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asi=
an:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahom=
a, sans-serif">Opportunistic TLS is confidentiality without authentication,=
 because no effort is made to authenticate the endpoints of the transmissio=
n, and it is optional confidentiality due to the ability to fall back to tr=
ansmission in the clear if a secure connection cannot be established. That =
said, most modern implementations of the SMTP protocol support this method,=
 especially at the largest mailbox providers, and so the vast majority of e=
mail traffic is encrypted during its time transiting from the client to the=
 server.=C2=A0</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;m=
argin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-w=
eight:700;font-variant-numeric:normal;font-variant-east-asian:normal;vertic=
al-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">5=
.2 Required Confidentiality, with Authentication</font></span></p><p dir=3D=
"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span s=
tyle=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-a=
sian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tah=
oma, sans-serif">Two protocols exist that move message confidentiality from=
 optional to required - MTA-STS [RFC8461] and DANE for SMTP [RFC7672]. Whil=
e they differ in their implementation details, SMTP servers relying on eith=
er protocol are stating that they only accept mail if the transmission can =
be encrypted with TLS, and a failure to negotiate a secure connection MUST =
result in the SMTP client refusing to transmit the message. Support for bot=
h protocols is widening, but is not yet mandatory.</font></span></p><p dir=
=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><spa=
n style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-eas=
t-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"=
tahoma, sans-serif">These two protocols differ from Opportunistic TLS not o=
nly because they require message confidentiality, but also because they req=
uire authentication.</font></span></p><p dir=3D"ltr" style=3D"line-height:1=
.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);=
font-weight:700;font-variant-numeric:normal;font-variant-east-asian:normal;=
vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-se=
rif">5.3 Message-Level Authentication</font></span></p><p dir=3D"ltr" style=
=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"col=
or:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian:normal=
;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-s=
erif">Protocols exist to allow for authentication of different identities a=
ssociated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A third=
 protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for validation =
of the domain in the visible From header, and a fourth, ARC [RFC8617], prov=
ides a way for each hop to record results of authentication checks performe=
d at that hop.</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;m=
argin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-v=
ariant-numeric:normal;font-variant-east-asian:normal;vertical-align:baselin=
e;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">All of these are =
outside the scope of this document, as they are outside the scope of the SM=
TP protocol. They deal with authentication of the message, not the endpoint=
s.</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0p=
t;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-weight:700;fo=
nt-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:bas=
eline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">5.4 Message-L=
evel Confidentiality</font></span></p><p dir=3D"ltr" style=3D"line-height:1=
.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);=
font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:b=
aseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif" style=3D"">=
The more sophisticated among the end users of SMTP may take advantage of va=
rious third party solutions that are designed to encrypt their message imme=
diately upon leaving the MUA, and to do so in such a way that only the indi=
vidual message recipient(s) can decrypt the message. The solutions (e.g., P=
GP) are too numerous to list here, and as they operate at the message level=
 rather than the SMTP protocol level, they are out of scope for this docume=
nt.</font></span></p><div class=3D"gmail_default" style=3D"font-family:taho=
ma,sans-serif">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D</div><div><br></div><div><div class=3D"gmail_default"=
 style=3D"font-family:tahoma,sans-serif">Have at it...</div><br></div></spa=
n></div></div><div><br></div>-- <br><div dir=3D"ltr" class=3D"gmail_signatu=
re"><span><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-b=
ottom:0pt"></p><div style=3D"text-align:left"><span style=3D"vertical-align=
:baseline;white-space:pre-wrap;font-size:small;font-family:Arial"><b>Todd H=
err </b></span><b></b><span style=3D"font-family:Arial;font-size:small;whit=
e-space:pre-wrap"> | Technical Director, Standards and Ecosystem</span></di=
v><span style=3D"vertical-align:baseline;white-space:pre-wrap;font-size:sma=
ll;font-family:Arial"><div style=3D"text-align:left"><span style=3D"vertica=
l-align:baseline"><b>e:</b></span><span style=3D"vertical-align:baseline"> =
<a href=3D"mailto:todd.herr@valimail.com" target=3D"_blank">todd.herr@valim=
ail.com</a> </span></div></span><span><div><span><b>m:</b></span><span> 703=
.220.4153</span><span></span></div><div style=3D"text-align:left"><img styl=
e=3D"width: 175px; height: 43px;" src=3D"https://hosted-packages.s3-us-west=
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ckground-color:rgb(255,255,255);line-height:1.38;margin-top:0pt;margin-bott=
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From: Dave Crocker <dhc@dcrocker.net>
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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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On 1/25/2022 1:21 PM, Todd Herr wrote:
> Here is my post-interim suggestion for text to use in the A/S to cover 
> the topics of Confidentiality and Authentication
> 
> =================================================== cut here 
> ===============================================
> 
> 5. Confidentiality and Authentication with SMTP
> 
> The default method for transmitting text using the SMTP protocol is to 
> do so “in the clear”. 

I suggest not casting it as the default.  It's not that the statement is 
wrong, but I think it sets the stage in a way that casts the protection 
mechanisms as exception.

So, perhaps:

SMTP is specified without embedded mechanisms for authentication or 
confidentiality.  Its traffic is therefore "in the clear".

>     Years of operational experience have shown that 
> such transmission exposes the message to easy compromise. 

... comprise, including wiretapping and spoofing.

 >  To mitigate
> this risk, 

these risks


SMTP has evolved over the years to allow for easy integration
> and support of Transport Layer Security (TLS - RFC8446) to provide both 
> confidentiality and authentication in the transmission of messages. 

Hmmmm.  I think SMTP has not evolved at all.  What has evolved is the 
operational choice to run it over TLS.  Have I missed changes to SMTP, 
itself?

If my understanding is correct, then perhaps:

Operation of SMTP has evolved over the years, so that it is used with 
the benefit of Transport Layer...


 >
This
> section will discuss those topics and their most common uses.

will discuss -> discusses

> 
> It is important that the reader understands what is meant by the terms 

understands -> understand

> “Authentication” and “Confidentiality”, and for that we will borrow 
> directly from RFC8446.
> 
>   *
> 
>     Authentication is the process of establishing the identity of the
>     endpoints (e.g., the hosts) of the SMTP transaction
> 
>   *
> 
>     The term “confidentiality” describes a state where the data (i.e.,
>     the message) is transmitted in a way that it is only visible to the
>     endpoints.
> 
> It is not uncommon for implementers to use the term “encryption” to mean 
> “confidentiality”, but this is not quite correct. Rather, encryption 
> using TLS is the current method by which confidentiality is achieved 
> with SMTP, but that does not mean that future methods might not be 
> developed.

nicely written!

A point of clarification worth adding, especially since it is usually 
missed but is extremely important:

      Note: With typical email use of TLS, authentication only is
            performed for the target receiving server and is not done for
            the sending client.  That is, it serves to validate that the
            connection has been made to the intended server, but does not
            validate who initiated it.

It's probably worth hammering this point a bit, such as changing any 
reference to authentication to be "receiving server authentication" or 
somesuch.


> 
> 5.1 Optional Confidentiality
> 
> The most common implementation of message confidentiality is what’s 
> known as “opportunistic TLS”, which is frequently referred to as 
> “opportunistic encryption”. With this method, an SMTP server announces 
> in its greeting that it is capable of supporting TLS encryption through 
> the presence of the “STARTTLS” keyword. The SMTP client then attempts to 
> negotiate an encrypted connection, and if successful, transmits the 
> message in encrypted form; there is no guarantee that the message will 
> be stored in encrypted fashion at its destination, and in fact, storage 
> in plain text should be expected. If negotiation fails, the client falls 
> back to sending the message in clear text.

Since I think this needs very strong emphasis, perhaps breaking out and 
indenting the 'no guarantee' text, such :

    Note: TLS provide protection while mail is in transit, but it does
          NOT mean that there is any mail encryption while the message is
          stored in a sever.  In fact, storage in plan text should be
          expected!


> Opportunistic TLS is confidentiality without authentication, because no 
> effort is made to authenticate the endpoints of the transmission, and it 
> is optional confidentiality due to the ability to fall back to 
> transmission in the clear if a secure connection cannot be established. 
> That said, most modern implementations of the SMTP protocol support this 
> method, especially at the largest mailbox providers, and so the vast 
> majority of email traffic is encrypted during its time transiting from 
> the client to the server.
> 
> 5.2 Required Confidentiality, with Authentication
> 
> Two protocols exist that move message confidentiality from optional to 
> required - MTA-STS [RFC8461] and DANE for SMTP [RFC7672]. While they 
> differ in their implementation details, SMTP servers relying on either 
> protocol are stating that they only accept mail if the transmission can 
> be encrypted with TLS, and a failure to negotiate a secure connection 
> MUST result in the SMTP client refusing to transmit the message. Support 
> for both protocols is widening, but is not yet mandatory.

widening -> increasing


> 
> These two protocols differ from Opportunistic TLS not only because they 
> require message confidentiality, but also because they require 
> authentication.

since TLS provides confidentiality, I think the requirement for 
authentication is the only difference.


> 
> 5.3 Message-Level Authentication
> 
> Protocols exist to allow for authentication of different identities 
> associated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A 
> third protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for 
> validation of the domain in the visible From header, and a fourth, ARC 
> [RFC8617], provides a way for each hop to record results of 
> authentication checks performed at that hop.
> 
> All of these are outside the scope of this document, as they are outside 
> the scope of the SMTP protocol. They deal with authentication of the 
> message, not the endpoints.

the SMTP protocol -> SMTP

(the P in SMTP stands for "protocol"...)


> 
> 5.4 Message-Level Confidentiality
> 
> The more sophisticated among the end users of SMTP may take advantage of 
> various third party solutions that are designed to encrypt their message 
> immediately upon leaving the MUA, and to do so in such a way that only 
> the individual message recipient(s) can decrypt the message. The 
> solutions (e.g., PGP) are too numerous to list here, and as they operate 
> at the message level rather than the SMTP protocol level, they are out 
> of scope for this document.

Since S/MIME and OpenPGP have RFCs, I suggest citing them, though noting 
that there are many proprietary solutions in use is reasonable, of course.


> 
> =================================================== cut here 
> ===============================================
> 
> Have at it...
yum...



d/


-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


From nobody Tue Jan 25 15:39:38 2022
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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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On 2022-01-25 3:27 p.m., Dave Crocker wrote:
> On 1/25/2022 1:21 PM, Todd Herr wrote:
>> Here is my post-interim suggestion for text to use in the A/S to cover 
>> the topics of Confidentiality and Authentication
>>
>> =================================================== cut here 
>> ===============================================
>>
>> 5. Confidentiality and Authentication with SMTP
>>
>> The default method for transmitting text using the SMTP protocol is to 
>> do so “in the clear”. 
> 
> I suggest not casting it as the default.  It's not that the statement is 
> wrong, but I think it sets the stage in a way that casts the protection 
> mechanisms as exception.
> 
> So, perhaps:
> 
> SMTP is specified without embedded mechanisms for authentication or 
> confidentiality.  Its traffic is therefore "in the clear".

"The original SMTP specification was created before embedded mechanisms 
for authentication or confidentiality became the norm. As such, it's 
traffic can be transmitted "in the clear", with the accompanying risk of 
exposing sensitive information, including passwords."

Does that sound better? It's a clear indication that it's time to do 
things differently than the original specifications.


-- 
"Catch the Magic of Linux..."
------------------------------------------------------------------------
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Visit us at http://www.linuxmagic.com @linuxmagic
A Wizard IT Company - For More Info http://www.wizard.ca
"LinuxMagic" a Registered TradeMark of Wizard Tower TechnoServices Ltd.
------------------------------------------------------------------------
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To: Michael Peddemors <michael@linuxmagic.com>, emailcore@ietf.org
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From: Dave Crocker <dhc@dcrocker.net>
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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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On 1/25/2022 3:39 PM, Michael Peddemors wrote:
> "The original SMTP specification was created before embedded mechanisms 
> for authentication or confidentiality became the norm. As such, it's 
> traffic can be transmitted "in the clear", with the accompanying risk of 
> exposing sensitive information, including passwords."
> 
> Does that sound better? It's a clear indication that it's time to do 
> things differently than the original specifications.


First, nothing being done now changes SMTP.  It changes packaging around 
SMTP.  This is not a minor point.  This is, therefore, a matter of 
changes to the 'service' rather than to the 'protocol', and certainly 
not to the specification of the protocol.

Second, the historical perspective is interesting briefly, perhaps, but 
is not interesting or useful for the long term.  That's why the phrasing 
I chose focuses on simple technical differences and does not have to 
tone of judgement about deficiencies in the past or superiority of the 
present.

d/

-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


From nobody Tue Jan 25 15:58:36 2022
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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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On 2022-01-25 1:21 p.m., Todd Herr wrote:
> 5.2 Required Confidentiality, with Authentication
> 
> Two protocols exist that move message confidentiality from optional to 
> required - MTA-STS [RFC8461] and DANE for SMTP [RFC7672]. While they 
> differ in their implementation details, SMTP servers relying on either 
> protocol are stating that they only accept mail if the transmission can 
> be encrypted with TLS, and a failure to negotiate a secure connection 
> MUST result in the SMTP client refusing to transmit the message. Support 
> for both protocols is widening, but is not yet mandatory.
> 
> These two protocols differ from Opportunistic TLS not only because they 
> require message confidentiality, but also because they require 
> authentication.
> 

Sorry, won't make any suggestions on this section, but do want to point 
out this is unclear, as it makes a statement about server-server 
communication, and then speaks about the SMTP client which is confusing.

Are we missing something here as well?

Another example of 'Required Confidentiality' is when a server does not 
allow authentication without SSL or TLS encryption for sending.  Is 
there something you can reference, that speaks directly to supporting 
plain text authentication is no longer recommended?


-- 
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From nobody Wed Jan 26 13:49:46 2022
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Date: Wed, 26 Jan 2022 16:49:18 -0500
From: John C Klensin <john-ietf@jck.com>
To: Todd Herr <todd.herr=40valimail.com@dmarc.ietf.org>, emailcore@ietf.org
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Subject: Re: [Emailcore] Ticket #54 - Take Two - Authentication and Encryption for A/S
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--On Monday, January 24, 2022 18:18 -0500 Todd Herr
<todd.herr=40valimail.com@dmarc.ietf.org> wrote:

> Greetings.
> 
> Thanks to all who attended the interim on January 21.
> 
> I've listened to the recording a couple of times and reviewed
> the notes (
> https://notes.ietf.org/notes-emailcore-interim-jan-2022) in an
> effort to propose better text for the subject topic. Before I
> really start writing, though, I want to throw the following
> outline to the group to see if it's directionally correct.
> 
>    - Define encryption (transmitting messages in ciphertext,
> rather than in    the clear, to provide privacy of
> communication) and authentication    (establishing the
> identity of the hosts involved in the transaction), both
> done using TLS.
>    - Discuss opportunistic TLS (sometimes called opportunistic
> encryption)    and mention that it's encryption without
> authentication.    - Discuss MTA-STS and DANE for SMTP, which
> are both encryption with    authentication.
>    - Mention SPF, DKIM, DMARC, and ARC, which are
> authentication protocols,    but not the kind of
> authentication we're talking about here.    - Mention private
> use message encryption (e.g., PGP) but only for the
> purposes of mentioning that it's out of scope for the A/S
> 
> Appreciate your collective feedback, to include suggested text
> for the definitions of encryption and authentication.

Todd,

(personal opinion only)
I've read your later note, but think I should respond to this
one.

First, I agree, plus or minus wordsmithing, with Dave Crocker's
suggestions.

However, if we are going down this path, I think it is important
to be very precise.    Two examples:

* At least as far as I know, none of the TLS-based techniques
provide confidentiality from submission to delivery or even from
the first entry into the SMTP system until the message reaches
the delivery server (as RFC 5321 defines that term), at least
unless it can be guaranteed that there will be a direct
connection between those two systems (i.e., no MX or other
relays that need to have at least the envelope in clear to route
the message or even post-delivery processing before the
receiving user gets the message into an MUA or equivalent).
The distinction is, or at least used to be, important because,
with the exception of attacks by governments, there were far
more successful attacks on servers than on network
infrastructure.  On the other hand, if the concerns about link
encryption really are about protection from government snooping,
it may be time we get much more clear about that.

* It is also important to distinguish between authentication of
the person who originated the message, authentication of the
originating system (submission server or first-hop MTA), and
authorization of the sending address to initiate messages from
that sending system and/or domain.   

While I hope everyone reading this is familiar with the above
(whether they agree with me or not), the likely audience for the
A/S may not be and we should not mislead them by, e.g., using
phrases like "Confidentiality between Endpoints" without
defining that very carefully and/or describing its limitations.

In addition, I have noticed that
draft-ietf-lamps-e2e-mail-guidance appears to be progressing in
the LAMPS WG.  Someone may want to start coordinating soon
because it would be really unfortunate to end up with guidance
about email from LAMPS that was inconsistent with guidance from
EMAILCORE... and perhaps even more unfortunate to discover the
conflicts during IETF Last Call on one document or the other.

best,
   john


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Subject: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 3
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--0000000000002dea9f05d6985144
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Greetings.

I've taken your comments under consideration, have incorporated many of
them, and have made a few other edits to boot.

The following text is the latest proposed text for this section of the A/S,
and will also be added to Ticket 54.

=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D

5. Confidentiality and Authentication with SMTP

SMTP is specified without embedded mechanisms for authentication or
confidentiality; its traffic is therefore =E2=80=9Cin the clear=E2=80=9D. Y=
ears of
operational experience have shown that such transmission exposes the
message to easy compromise, including wiretapping and spoofing. To mitigate
these risks, operation of SMTP has evolved over the years so that it is
used with the benefit of Transport Layer Security (TLS - RFC8446) to
provide both confidentiality and authentication in the transmission of
messages. This section discusses those topics and their most common uses.

It is important that the reader understand what is meant by the terms
=E2=80=9CAuthentication=E2=80=9D and =E2=80=9CConfidentiality=E2=80=9D, and=
 for that we will borrow
directly from RFC8446.

   -

   Authentication is the process of establishing the identity of one or
   more of the endpoints of a communication channel. TLS only requires
   authentication of the server side of the communication channel;
   authentication of the client side is optional.
   -

   The term =E2=80=9Cconfidentiality=E2=80=9D describes a state where the d=
ata (i.e., the
   message) is transmitted in a way that it is only visible to the endpoint=
s
   of a communication channel.

It is not uncommon for implementers to use the term =E2=80=9Cencryption=E2=
=80=9D to mean
=E2=80=9Cconfidentiality=E2=80=9D, but this is not quite correct. Rather, e=
ncryption using
TLS is the current method by which confidentiality is achieved with SMTP,
but that does not mean that future methods might not be developed.

Note: With typical email use of TLS, authentication only is performed for
the target receiving server and is not done for the sending client. That
is, it serves to validate that the connection has been made to the intended
server, but does not validate who initiated it.

5.1 Optional Confidentiality

The most common implementation of message confidentiality is what=E2=80=99s=
 known
as =E2=80=9Copportunistic TLS=E2=80=9D, which is frequently referred to as =
=E2=80=9Copportunistic
encryption=E2=80=9D. With this method, a receiving server announces in its =
greeting
that it is capable of supporting TLS encryption through the presence of the
=E2=80=9CSTARTTLS=E2=80=9D keyword. The sending client then attempts to neg=
otiate an
encrypted connection, and if successful, transmits the message in encrypted
form; if negotiation fails, the client falls back to sending the message in
clear text.

Opportunistic TLS is confidentiality without authentication, because no
effort is made to authenticate the receiving server, and it is optional
confidentiality due to the ability to fall back to transmission in the
clear if a secure connection cannot be established. That said, most modern
implementations of SMTP support this method, especially at the largest
mailbox providers, and so the vast majority of email traffic is encrypted
during its time transiting from the client to the server.

Note: While TLS provides protection while the message is in transit, there
is no guarantee that the message will be stored in encrypted fashion at its
destination. In fact, storage in plain text should be expected!

5.2 Required Confidentiality, with Receiving Server Authentication

Two protocols exist that move message confidentiality from optional to
required (with conditions as noted below) - MTA-STS [RFC8461] and DANE for
SMTP [RFC7672]. While they differ in their implementation details,
receiving servers relying on either protocol are stating that they only
accept mail if the transmission can be encrypted with TLS, and a failure to
negotiate a secure connection MUST result in the sending client refusing to
transmit the message. Support for both protocols is increasing, but is not
yet mandatory.

These two protocols differ from Opportunistic TLS in that they require
receiving server authentication and there is no fallback to sending in the
clear if negotiation of an encrypted connection fails.

Note: Both protocols mentioned in this section rely not only on the
receiving server but also the sending client supporting the protocol
intended to be used. If the sending client does not implement or understand
the protocol requested by the receiving server, the sending client will use
Opportunistic TLS or clear-text to transmit the message.

5.3 Message-Level Authentication

Protocols exist to allow for authentication of different identities
associated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A
third protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for
validation of the domain in the visible From header, and a fourth, ARC
[RFC8617], provides a way for each hop to record results of authentication
checks performed at that hop.

All of these are outside the scope of this document, as they are outside
the scope of SMTP. They deal with validating the authorized usage of one or
more domains in an email message, and not with establishing the identity of
the receiving server.

5.4 SMTP Authentication

SMTP Authentication, which is often abbreviated as SMTP AUTH, is an
extension to SMTP. While its name might suggest that it would be within
scope for this section of the Applicability Statement, nothing could be
further from the truth.

SMTP AUTH defines a method for a client to identify itself to a Message
Submission Agent (MSA) when presenting a message for transmission, usually
using port 587 rather than the traditional port 25. The most common
implementation of SMTP AUTH is for a person to present a username and
password to their mailbox provider=E2=80=99s outbound SMTP server when conf=
iguring
their MUA for sending mail.

5.5 Message-Level Confidentiality

Protocols such as S/MIME (RFC8551) and OpenPGP (RFC4880) exist to allow for
message confidentiality outside of the operation of SMTP. That is to say,
using these protocols results in encryption of the message prior to its
being submitted to the SMTP communications channel, and decryption of the
message is the responsibility of the message recipient. There are numerous
implementations of these protocols, too many to list here. As they operate
fully independent of SMTP, they are out of scope for this document.
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D





--=20

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
*m:* 703.220.4153

This email and all data transmitted with it contains confidential and/or
proprietary information intended solely for the use of individual(s)
authorized to receive it. If you are not an intended and authorized
recipient you are hereby notified of any use, disclosure, copying or
distribution of the information included in this transmission is prohibited
and may be unlawful. Please immediately notify the sender by replying to
this email and then delete it from your system.

--0000000000002dea9f05d6985144
Content-Type: text/html; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

<div dir=3D"ltr"><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
ans-serif">Greetings.<br clear=3D"all"></div><div class=3D"gmail_default" s=
tyle=3D"font-family:tahoma,sans-serif"><br></div><div class=3D"gmail_defaul=
t" style=3D"font-family:tahoma,sans-serif">I&#39;ve taken your comments und=
er consideration, have incorporated many of them, and have made a few other=
 edits to boot.</div><div class=3D"gmail_default" style=3D"font-family:taho=
ma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-family:=
tahoma,sans-serif">The following text is the latest proposed=C2=A0text for =
this section of the A/S, and will also be added to Ticket 54.</div><div cla=
ss=3D"gmail_default" style=3D"font-family:tahoma,sans-serif"><br></div><div=
 class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif">=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D cu=
t here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D</div><div class=3D"gmail_default" style=3D""><span id=3D"gmail-do=
cs-internal-guid-8eb767ea-7fff-8e17-3287-ff276b2de8da" style=3D""><p dir=3D=
"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span s=
tyle=3D"color:rgb(89,89,89);font-weight:700;font-variant-numeric:normal;fon=
t-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"><=
font face=3D"tahoma, sans-serif" style=3D"">5. Confidentiality and Authenti=
cation with SMTP</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656=
;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font=
-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:basel=
ine;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">SMTP is specifi=
ed without embedded mechanisms for authentication or confidentiality; its t=
raffic is therefore =E2=80=9Cin the clear=E2=80=9D. Years of operational ex=
perience have shown that such transmission exposes the message to easy comp=
romise, including wiretapping and spoofing. To mitigate these risks, operat=
ion of SMTP has evolved over the years so that it is used with the benefit =
of Transport Layer Security (TLS - RFC8446) to provide both confidentiality=
 and authentication in the transmission of messages. This section discusses=
 those topics and their most common uses.</font></span></p><p dir=3D"ltr" s=
tyle=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D=
"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian:no=
rmal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sa=
ns-serif">It is important that the reader understand what is meant by the t=
erms =E2=80=9CAuthentication=E2=80=9D and =E2=80=9CConfidentiality=E2=80=9D=
, and for that we will borrow directly from RFC8446.</font></span></p><ul s=
tyle=3D"margin-top:0px;margin-bottom:0px"><li dir=3D"ltr" style=3D"list-sty=
le-type:disc;color:rgb(89,89,89);background-color:transparent;font-variant-=
numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;white=
-space:pre"><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin=
-bottom:0pt" role=3D"presentation"><span style=3D"font-variant-numeric:norm=
al;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre-w=
rap"><font face=3D"tahoma, sans-serif">Authentication is the process of est=
ablishing the identity of one or more of the endpoints of a communication c=
hannel. TLS only requires authentication of the server side of the communic=
ation channel; authentication of the client side is optional.</font></span>=
</p></li><li dir=3D"ltr" style=3D"list-style-type:disc;color:rgb(89,89,89);=
background-color:transparent;font-variant-numeric:normal;font-variant-east-=
asian:normal;vertical-align:baseline;white-space:pre"><p dir=3D"ltr" style=
=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt" role=3D"presentati=
on"><span style=3D"font-variant-numeric:normal;font-variant-east-asian:norm=
al;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans=
-serif">The term =E2=80=9Cconfidentiality=E2=80=9D describes a state where =
the data (i.e., the message) is transmitted in a way that it is only visibl=
e to the endpoints of a communication channel.</font></span></p></li></ul><=
p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"=
><span style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-varian=
t-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font fac=
e=3D"tahoma, sans-serif">It is not uncommon for implementers to use the ter=
m =E2=80=9Cencryption=E2=80=9D to mean =E2=80=9Cconfidentiality=E2=80=9D, b=
ut this is not quite correct. Rather, encryption using TLS is the current m=
ethod by which confidentiality is achieved with SMTP, but that does not mea=
n that future methods might not be developed.</font></span></p><p dir=3D"lt=
r" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span styl=
e=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asia=
n:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma=
, sans-serif">Note: With typical email use of TLS, authentication only is p=
erformed for the target receiving server and is not done for the sending cl=
ient. That is, it serves to validate that the connection has been made to t=
he intended server, but does not validate who initiated it.</font></span></=
p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12=
pt"><span style=3D"color:rgb(89,89,89);font-weight:700;font-variant-numeric=
:normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:=
pre-wrap"><font face=3D"tahoma, sans-serif">5.1 Optional Confidentiality</f=
ont></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;mar=
gin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-variant-numeric:no=
rmal;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre=
-wrap"><font face=3D"tahoma, sans-serif">The most common implementation of =
message confidentiality is what=E2=80=99s known as =E2=80=9Copportunistic T=
LS=E2=80=9D, which is frequently referred to as =E2=80=9Copportunistic encr=
yption=E2=80=9D. With this method, a receiving server announces in its gree=
ting that it is capable of supporting TLS encryption through the presence o=
f the =E2=80=9CSTARTTLS=E2=80=9D keyword. The sending client then attempts =
to negotiate an encrypted connection, and if successful, transmits the mess=
age in encrypted form; if negotiation fails, the client falls back to sendi=
ng the message in clear text.</font></span></p><p dir=3D"ltr" style=3D"line=
-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(8=
9,89,89);font-variant-numeric:normal;font-variant-east-asian:normal;vertica=
l-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">Op=
portunistic TLS is confidentiality without authentication, because no effor=
t is made to authenticate the receiving server, and it is optional confiden=
tiality due to the ability to fall back to transmission in the clear if a s=
ecure connection cannot be established. That said, most modern implementati=
ons of SMTP support this method, especially at the largest mailbox provider=
s, and so the vast majority of email traffic is encrypted during its time t=
ransiting from the client to the server.=C2=A0</font></span></p><p dir=3D"l=
tr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span sty=
le=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asi=
an:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahom=
a, sans-serif">Note: While TLS provides protection while the message is in =
transit, there is no guarantee that the message will be stored in encrypted=
 fashion at its destination. In fact, storage in plain text should be expec=
ted!</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:=
0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-weight:700;=
font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:b=
aseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">5.2 Require=
d Confidentiality, with Receiving Server Authentication</font></span></p><p=
 dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt">=
<span style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant=
-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=
=3D"tahoma, sans-serif">Two protocols exist that move message confidentiali=
ty from optional to required (with conditions as noted below) - MTA-STS [RF=
C8461] and DANE for SMTP [RFC7672]. While they differ in their implementati=
on details, receiving servers relying on either protocol are stating that t=
hey only accept mail if the transmission can be encrypted with TLS, and a f=
ailure to negotiate a secure connection MUST result in the sending client r=
efusing to transmit the message. Support for both protocols is increasing, =
but is not yet mandatory.</font></span></p><p dir=3D"ltr" style=3D"line-hei=
ght:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89=
,89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-al=
ign:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">These =
two protocols differ from Opportunistic TLS in that they require receiving =
server authentication and there is no fallback to sending in the clear if n=
egotiation of an encrypted connection fails.</font></span></p><p dir=3D"ltr=
" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=
=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian=
:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma,=
 sans-serif">Note: Both protocols mentioned in this section rely not only o=
n the receiving server but also the sending client supporting the protocol =
intended to be used. If the sending client does not implement or understand=
 the protocol requested by the receiving server, the sending client will us=
e Opportunistic TLS or clear-text to transmit the message.</font></span></p=
><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12p=
t"><span style=3D"color:rgb(89,89,89);font-weight:700;font-variant-numeric:=
normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:p=
re-wrap"><font face=3D"tahoma, sans-serif">5.3 Message-Level Authentication=
</font></span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;=
margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);font-variant-numeric=
:normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:=
pre-wrap"><font face=3D"tahoma, sans-serif">Protocols exist to allow for au=
thentication of different identities associated with an email message - SPF=
 [RFC7208] and DKIM [RFC6376]. A third protocol, DMARC [RFC7489], relies on=
 SPF and DKIM to allow for validation of the domain in the visible From hea=
der, and a fourth, ARC [RFC8617], provides a way for each hop to record res=
ults of authentication checks performed at that hop.</font></span></p><p di=
r=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><sp=
an style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D=
"tahoma, sans-serif">All of these are outside the scope of this document, a=
s they are outside the scope of SMTP. They deal with validating the authori=
zed usage of one or more domains in an email message, and not with establis=
hing the identity of the receiving server.</font></span></p><p dir=3D"ltr" =
style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=
=3D"color:rgb(89,89,89);font-weight:700;font-variant-numeric:normal;font-va=
riant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font=
 face=3D"tahoma, sans-serif">5.4 SMTP Authentication</font></span></p><p di=
r=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><sp=
an style=3D"color:rgb(89,89,89);font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre-wrap"><font face=3D=
"tahoma, sans-serif">SMTP Authentication, which is often abbreviated as SMT=
P AUTH, is an extension to SMTP. While its name might suggest that it would=
 be within scope for this section of the Applicability Statement, nothing c=
ould be further from the truth.</font></span></p><p dir=3D"ltr" style=3D"li=
ne-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb=
(89,89,89);font-variant-numeric:normal;font-variant-east-asian:normal;verti=
cal-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-serif">=
SMTP AUTH defines a method for a client to identify itself to a Message Sub=
mission Agent (MSA) when presenting a message for transmission, usually usi=
ng port 587 rather than the traditional port 25. The most common implementa=
tion of SMTP AUTH is for a person to present a username and password to the=
ir mailbox provider=E2=80=99s outbound SMTP server when configuring their M=
UA for sending mail.</font></span></p><p dir=3D"ltr" style=3D"line-height:1=
.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,89);=
font-weight:700;font-variant-numeric:normal;font-variant-east-asian:normal;=
vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-se=
rif">5.5 Message-Level Confidentiality</font></span></p><p dir=3D"ltr" styl=
e=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"co=
lor:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian:norma=
l;vertical-align:baseline;white-space:pre-wrap"><font face=3D"tahoma, sans-=
serif" style=3D"">Protocols such as S/MIME (RFC8551) and OpenPGP (RFC4880) =
exist to allow for message confidentiality outside of the operation of SMTP=
. That is to say, using these protocols results in encryption of the messag=
e prior to its being submitted to the SMTP communications channel, and decr=
yption of the message is the responsibility of the message recipient. There=
 are numerous implementations of these protocols, too many to list here. As=
 they operate fully independent of SMTP, they are out of scope for this doc=
ument.</font></span></p><div class=3D"gmail_default" style=3D"font-family:t=
ahoma,sans-serif">=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D cut here =3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=
=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D=3D</div><p dir=3D"ltr" style=3D"line-heig=
ht:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"color:rgb(89,89,=
89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-ali=
gn:baseline;white-space:pre-wrap"></span></p><div class=3D"gmail_default"><=
span id=3D"gmail-docs-internal-guid-8eb767ea-7fff-8e17-3287-ff276b2de8da"><=
br class=3D"gmail-Apple-interchange-newline"></span></div></span><br class=
=3D"gmail-Apple-interchange-newline"></div><div class=3D"gmail_default" sty=
le=3D"font-family:tahoma,sans-serif"><br></div><div><br></div>-- <br><div d=
ir=3D"ltr" class=3D"gmail_signature" data-smartmail=3D"gmail_signature"><sp=
an><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:0=
pt"></p><div style=3D"text-align:left"><span style=3D"vertical-align:baseli=
ne;white-space:pre-wrap;font-size:small;font-family:Arial"><b>Todd Herr </b=
></span><b></b><span style=3D"font-family:Arial;font-size:small;white-space=
:pre-wrap"> | Technical Director, Standards and Ecosystem</span></div><span=
 style=3D"vertical-align:baseline;white-space:pre-wrap;font-size:small;font=
-family:Arial"><div style=3D"text-align:left"><span style=3D"vertical-align=
:baseline"><b>e:</b></span><span style=3D"vertical-align:baseline"> <a href=
=3D"mailto:todd.herr@valimail.com" target=3D"_blank">todd.herr@valimail.com=
</a> </span></div></span><span><div><span><b>m:</b></span><span> 703.220.41=
53</span><span></span></div><div style=3D"text-align:left"><img style=3D"wi=
dth:175px;height:43px" src=3D"https://hosted-packages.s3-us-west-1.amazonaw=
s.com/Valimail+Logo.png"></div></span><p dir=3D"ltr" style=3D"background-co=
lor:rgb(255,255,255);line-height:1.38;margin-top:0pt;margin-bottom:0pt"><fo=
nt face=3D"Arial" color=3D"#666666"><span style=3D"font-size:10.6667px;whit=
e-space:pre-wrap">This email and all data transmitted with it contains conf=
idential and/or proprietary information intended solely for the use of indi=
vidual(s) authorized to receive it. If you are not an intended and authoriz=
ed recipient you are hereby notified of any use, disclosure, copying or dis=
tribution of the information included in this transmission is prohibited an=
d may be unlawful. Please immediately notify the sender by replying to this=
 email and then delete it from your system.</span></font></p></span></div><=
/div>

--0000000000002dea9f05d6985144--


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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 3
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On 1/27/2022 3:02 PM, Todd Herr wrote:
...
> Note: With typical email use of TLS, authentication only is performed 
> for the target receiving server and is not done for the sending client. 
> That is, it serves to validate that the connection has been made to the 
> intended server, but does not validate who initiated it.

I think this has my wording and I now see the first sentence might be 
misinterpreted, since it isn't clear who is authenticating whom.  I suggest:


Note: With typical email use of TLS, authentication only is performed by 
the sending client of the target receiving server. That is, it serves to 
validate that the connection has been made to the intended server, but 
does not validate who initiated it.


> 5.1 Optional Confidentiality
...
> 
> Note: While TLS provides protection while the message is in transit, 
> there is no guarantee that the message will be stored in encrypted 
> fashion at its destination. In fact, storage in plain text should be 
> expected!

To respond to the significant concern that was raised that the reader 
properly understand that this is hop-by-hop wire encryption and is not 
end-to-end, I suggest:

Note: While TLS provides protection while the message is in transit for 
a single SMTP connection, a message that is encrypted for one SMTP hop 
might not be encrypted on the next hop and it might not be encrypted 
within MTAs relaying the message or at its destination. In fact, storage 
in plain text should be expected!



> 5.2 Required Confidentiality, with Receiving Server Authentication
> 
> Two protocols exist that move message confidentiality from optional to 
> required (with conditions as noted below) - MTA-STS [RFC8461] and DANE 
> for SMTP [RFC7672]. While they differ in their implementation details, 
> receiving servers relying on either protocol are stating that they only 
> accept mail if the transmission can be encrypted with TLS, and a failure 
> to negotiate a secure connection MUST result in the sending client 
> refusing to transmit the message. Support for both protocols is 
> increasing, but is not yet mandatory.
> 
> These two protocols differ from Opportunistic TLS in that they require 
> receiving server authentication and there is no fallback to sending in 
> the clear if negotiation of an encrypted connection fails.
> 
> Note: Both protocols mentioned in this section rely not only on the 
> receiving server but also the sending client supporting the protocol 
> intended to be used. If the sending client does not implement or 
> understand the protocol requested by the receiving server, the sending 
> client will use Opportunistic TLS or clear-text to transmit the message.
> 
> 5.3 Message-Level Authentication
> 
> Protocols exist to allow for authentication of different identities 
> associated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A 
> third protocol, DMARC [RFC7489], relies on SPF and DKIM to allow for 
> validation of the domain in the visible From header, and a fourth, ARC 
> [RFC8617], provides a way for each hop to record results of 
> authentication checks performed at that hop.
> 
> All of these are outside the scope of this document, as they are outside 
> the scope of SMTP. They deal with validating the authorized usage of one 
> or more domains in an email message, and not with establishing the 
> identity of the receiving server.
> 
> 5.4 SMTP Authentication
> 
> SMTP Authentication, which is often abbreviated as SMTP AUTH, is an 
> extension to SMTP. While its name might suggest that it would be within 
> scope for this section of the Applicability Statement, nothing could be 
> further from the truth.

I suspect many things could be further for the truth...  So perhaps some 
milder and more bording wording, such as:

    It doesn't.


> 
> SMTP AUTH defines a method for a client to identify itself to a Message 
> Submission Agent (MSA) when presenting a message for transmission, 
> usually using port 587 rather than the traditional port 25. The most 
> common implementation of SMTP AUTH is for a person to present a username 
> and password to their mailbox provider’s outbound SMTP server when 
> configuring their MUA for sending mail.
> 
> 5.5 Message-Level Confidentiality
> 

I'm not offering wording, but it might be worth using this section to 
introduce the terms Channel Security versus Object Security.  TLS is a 
channel-based mechanism. So is SPF.   S/MIME, OpenPGP, DKIM, DMARC and 
ARC are all Object based.  The simple description I'm used to, about the 
difference, is that Channel-based protects whatever bits go over the 
channel, without concern for the content, where Object-based is attached 
to the object and is not concerned with details of the Channel.


d/

-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


From nobody Fri Jan 28 08:37:41 2022
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Date: Fri, 28 Jan 2022 11:37:25 -0500
From: John C Klensin <john-ietf@jck.com>
To: Todd Herr <todd.herr=40valimail.com@dmarc.ietf.org>, emailcore@ietf.org
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Todd,

I think this is moving in the right direction.  However...

(1) Much of this seems to be a tutorial rather than clear
statements about things that people should or should not do.  I
wonder if such a tutorial reasonably falls within the scope of
EMAILCORE and, more specifically, if we should be encouraging
the Security ADs to make such a tutorial part of the LAMPS
effort that is working on draft-ietf-lamps-e2e-mail-guidance.
For similar reasons that are less related to the LAMPS work, it
is not clear to me why an Applicability Statement needs to spend
time discussing what it is not going to discuss.

Almost independent of that concern...

(2) If you are going to mention S/MIME and OpenPGP at all, you
should add that each can provide authentication as well as, or
in addition to confidentiality. In particular, given a few
assumptions about the ability of senders to manage keys (a much
broader issue and heavily dependent on the type of senders),
they provide much stronger authentication and message content
integrity protection than any of the other methods you mention.
Probably also worth mentioning that there are other mechanisms
(not standardized by the IETF) in that space and they do not
provide confidentiality for the SMTP envelope and, in general,
not even the message headers.

(3) Having read through the text several times, it is not likely
that a reader who is not very clear about all of these
mechanisms already will be able to figure out what is being
protected from either an authentication or confidentiality
standpoint.  At one extreme, S/MIME, OpenPGP, and friends
provide strong and sender to receiver authentication, integrity
protection, and/or confidentiality, but only for some or all of
the message content.   Other methods you describe may provide
greater protection for message headers and all or part of the
envelope information, but require that anyone wanting to trust
that confidentiality or authenticity have great trust in the
operators, servers, and systems that handle the message when it
is not actually on the wire.  IMO, failure to make those
distinctions clear significantly weakens the presentation and
may even turn it from "helpful" into "part of the problem and
dangerous".  The text you quoted takes a small step in the
direction I'm encouraging by pointing out that TLS often does
not involve authentication of the client, only the server (and,
by implication, does not authenticate the sender at all, only
some of the machines that handle the message).  Perhaps a chart
would be helpful.

best,
   john


--On Thursday, January 27, 2022 18:02 -0500 Todd Herr
<todd.herr=40valimail.com@dmarc.ietf.org> wrote:

> Greetings.
> 
> I've taken your comments under consideration, have
> incorporated many of them, and have made a few other edits to
> boot.
> 
> The following text is the latest proposed text for this
> section of the A/S, and will also be added to Ticket 54.
> 
> =========================== cut here =========================
> 
> 5. Confidentiality and Authentication with SMTP
> 
> SMTP is specified without embedded mechanisms for
> authentication or confidentiality; its traffic is therefore
> "in the clear". Years of operational experience have shown
> that such transmission exposes the message to easy compromise,
> including wiretapping and spoofing. To mitigate these risks,
> operation of SMTP has evolved over the years so that it is
> used with the benefit of Transport Layer Security (TLS -
> RFC8446) to provide both confidentiality and authentication in
> the transmission of messages. This section discusses those
> topics and their most common uses.
> 
> It is important that the reader understand what is meant by
> the terms "Authentication" and "Confidentiality", and
> for that we will borrow directly from RFC8446.
> 
>    -
> 
>    Authentication is the process of establishing the identity
> of one or    more of the endpoints of a communication channel.
> TLS only requires    authentication of the server side of the
> communication channel;    authentication of the client side is
> optional.
>    -
> 
>    The term "confidentiality" describes a state where the
> data (i.e., the    message) is transmitted in a way that it is
> only visible to the endpoints    of a communication channel.
> 
> It is not uncommon for implementers to use the term
> "encryption" to mean "confidentiality", but this is
> not quite correct. Rather, encryption using TLS is the current
> method by which confidentiality is achieved with SMTP, but
> that does not mean that future methods might not be developed.
> 
> Note: With typical email use of TLS, authentication only is
> performed for the target receiving server and is not done for
> the sending client. That is, it serves to validate that the
> connection has been made to the intended server, but does not
> validate who initiated it.
> 
> 5.1 Optional Confidentiality
> 
> The most common implementation of message confidentiality is
> what's known as "opportunistic TLS", which is frequently
> referred to as "opportunistic encryption". With this
> method, a receiving server announces in its greeting that it
> is capable of supporting TLS encryption through the presence
> of the "STARTTLS" keyword. The sending client then
> attempts to negotiate an encrypted connection, and if
> successful, transmits the message in encrypted form; if
> negotiation fails, the client falls back to sending the
> message in clear text.
> 
> Opportunistic TLS is confidentiality without authentication,
> because no effort is made to authenticate the receiving
> server, and it is optional confidentiality due to the ability
> to fall back to transmission in the clear if a secure
> connection cannot be established. That said, most modern
> implementations of SMTP support this method, especially at the
> largest mailbox providers, and so the vast majority of email
> traffic is encrypted during its time transiting from the
> client to the server.
> 
> Note: While TLS provides protection while the message is in
> transit, there is no guarantee that the message will be stored
> in encrypted fashion at its destination. In fact, storage in
> plain text should be expected!
> 
> 5.2 Required Confidentiality, with Receiving Server
> Authentication
> 
> Two protocols exist that move message confidentiality from
> optional to required (with conditions as noted below) -
> MTA-STS [RFC8461] and DANE for SMTP [RFC7672]. While they
> differ in their implementation details, receiving servers
> relying on either protocol are stating that they only accept
> mail if the transmission can be encrypted with TLS, and a
> failure to negotiate a secure connection MUST result in the
> sending client refusing to transmit the message. Support for
> both protocols is increasing, but is not yet mandatory.
> 
> These two protocols differ from Opportunistic TLS in that they
> require receiving server authentication and there is no
> fallback to sending in the clear if negotiation of an
> encrypted connection fails.
> 
> Note: Both protocols mentioned in this section rely not only
> on the receiving server but also the sending client supporting
> the protocol intended to be used. If the sending client does
> not implement or understand the protocol requested by the
> receiving server, the sending client will use Opportunistic
> TLS or clear-text to transmit the message.
> 
> 5.3 Message-Level Authentication
> 
> Protocols exist to allow for authentication of different
> identities associated with an email message - SPF [RFC7208]
> and DKIM [RFC6376]. A third protocol, DMARC [RFC7489], relies
> on SPF and DKIM to allow for validation of the domain in the
> visible From header, and a fourth, ARC [RFC8617], provides a
> way for each hop to record results of authentication checks
> performed at that hop.
> 
> All of these are outside the scope of this document, as they
> are outside the scope of SMTP. They deal with validating the
> authorized usage of one or more domains in an email message,
> and not with establishing the identity of the receiving server.
> 
> 5.4 SMTP Authentication
> 
> SMTP Authentication, which is often abbreviated as SMTP AUTH,
> is an extension to SMTP. While its name might suggest that it
> would be within scope for this section of the Applicability
> Statement, nothing could be further from the truth.
> 
> SMTP AUTH defines a method for a client to identify itself to
> a Message Submission Agent (MSA) when presenting a message for
> transmission, usually using port 587 rather than the
> traditional port 25. The most common implementation of SMTP
> AUTH is for a person to present a username and password to
> their mailbox provider's outbound SMTP server when
> configuring their MUA for sending mail.
> 
> 5.5 Message-Level Confidentiality
> 
> Protocols such as S/MIME (RFC8551) and OpenPGP (RFC4880) exist
> to allow for message confidentiality outside of the operation
> of SMTP. That is to say, using these protocols results in
> encryption of the message prior to its being submitted to the
> SMTP communications channel, and decryption of the message is
> the responsibility of the message recipient. There are numerous
> implementations of these protocols, too many to list here. As
> they operate fully independent of SMTP, they are out of scope
> for this document. =========================== cut here
> =========================



From nobody Mon Jan 31 07:46:56 2022
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A New Internet-Draft is available from the on-line Internet-Drafts directories.
This draft is a work item of the Revision of core Email specifications WG of the IETF.

        Title           : Applicability Statement for IETF Core Email Protocols
        Authors         : John C Klensin
                          Kenneth Murchison
                          E Sam
	Filename        : draft-ietf-emailcore-as-04.txt
	Pages           : 9
	Date            : 2022-01-31

Abstract:
   Electronic mail is one of the oldest Internet applications that is
   still in very active use.  While the basic protocols and formats for
   mail transport and message formats have evolved slowly over the
   years, events and thinking in more recent years have supplemented
   those core protocols with additional features and suggestions for
   their use.  This Applicability Statement describes the relationship
   among many of those protocols and provides guidance and makes
   recommendations for the use of features of the core protocols.


The IETF datatracker status page for this draft is:
https://datatracker.ietf.org/doc/draft-ietf-emailcore-as/

There is also an htmlized version available at:
https://datatracker.ietf.org/doc/html/draft-ietf-emailcore-as-04

A diff from the previous version is available at:
https://www.ietf.org/rfcdiff?url2=draft-ietf-emailcore-as-04


Internet-Drafts are also available by rsync at rsync.ietf.org::internet-drafts



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From: Alessandro Vesely <vesely@tana.it>
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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 3
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On Fri 28/Jan/2022 00:45:28 +0100 Dave Crocker wrote:
> On 1/27/2022 3:02 PM, Todd Herr wrote:
> ...
>> Note: With typical email use of TLS, authentication only is 
>> performed for the target receiving server and is not done for the 
>> sending client. That is, it serves to validate that the connection 
>> has been made to the intended server, but does not validate who 
>> initiated it.
> 
> I think this has my wording and I now see the first sentence might be 
> misinterpreted, since it isn't clear who is authenticating whom.  I 
> suggest:
> 
> 
> Note: With typical email use of TLS, authentication only is performed 
> by the sending client of the target receiving server. That is, it 
> serves to validate that the connection has been made to the intended 
> server, but does not validate who initiated it.


To be even more clear, I'd add something like "Sending client 
authentication is usually done on the first hop only, see Section 5.4".


>> [...]
>> 5.2 Required Confidentiality, with Receiving Server Authentication
>>
>> Two protocols exist [...] Support for both protocols is
>> increasing, but is not yet mandatory.

Mandatory -> widespread (or prevalent?) at the time of this writing.


jm2c
Ale
-- 








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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 3
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It appears that Alessandro Vesely  <vesely@tana.it> said:
>> Note: With typical email use of TLS, authentication only is performed 
>> by the sending client of the target receiving server. That is, it 
>> serves to validate that the connection has been made to the intended 
>> server, but does not validate who initiated it.
>
>To be even more clear, I'd add something like "Sending client 
>authentication is usually done on the first hop only, see Section 5.4".

I'm not sure whether you are referring to authentication OF the sending client
or BY the sending client, but either way, it seems wrong.

Authentication BY the client happens on a hop to a server located
using an MX or maybe A/AAAA record, using DANE or MTA-STS to check
that the server is the one it's looking for. All the other hops are
within the sending or receiving system which presumably has knowledge
if its internal structure so there's nothing to authenticate.

Authentication OF the client doesn't happen at all unless I supose
you're talking about DNS checks on the HELO name, or you're mixing
submission with SMTP.

R's,
John

