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Author: Alessandro Vesely <vesely@tana.it>
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Subject: [Emailcore] Should rfc5322bis register an Email Authentication Method to report overall format conformance?
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Hi all,

perhaps I should have questioned ietf-822 about this idea.  However, since the 
standard is now being revised, perhaps it makes more sense to ask here directly.

As is well known, RFC 8601 provides ways to describe the level of trust that a 
message is considered to deserve, according to a variety of methods, in an 
Authentication-Results: (A-R) header field.  Deep down, all methods rely on the 
mail format.  However, the format itself is not reported directly.

For example, a popular DKIM filter has an option to refuse processing of a 
message if the header field count does not conform to RFC5322 Section 3.6. 
That stems from inconsistencies among different software about how to treat 
anomalies such as multiple From: fields, which can result in authenticating a 
field which is not the one displayed.[*]

What to do in such cases?  The old message just exemplified[*] had a 
cryptographically correct A-R:

Authentication-Results: sbh17.songbird.com;
     dkim=pass (1024-bit key) header.i=@isdg.net

Since then, some mail sites adopted signatures where both From: fields are 
signed, the rightful one and the illicit, currently empty one.  That way, 
adding a non-empty From: breaks the signature.  A clever trick which works but 
is not informative.  Perhaps, an A-R for that case could be conceived like so:

Authentication-Results: server.example.com;
     mail=fail multiple.from;
     dkim=policy (invalid message) header.i=@whatever.example

That would indicate the failure point correctly.  At the same time, a mail= 
method would indicate that the mail format was checked.  IMHO, that would 
contribute to mail format compliance significantly, especially when MUAs 
display the result.  The standard could even provide for mail=obs.  Not banning 
but tagging.


jm2c
Ale
-- 

[*]
https://mailarchive.ietf.org/arch/msg/ietf-dkim/KEUcXBTzh_hvNrQns1nDJoqF2FY/









From nobody Sat Mar  5 18:20:16 2022
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Date: Sat, 05 Mar 2022 21:19:58 -0500
From: John C Klensin <john-ietf@jck.com>
To: John Levine <johnl@taugh.com>, Sabahattin Gucukoglu <listsebby@me.com>, emailcore@ietf.org
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Subject: Re: [Emailcore] 5321bis-09: Thinking About Interaction of Code 556 with 'postmaster'
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--On Monday, February 21, 2022 14:10 -0500 John Levine
<johnl@taugh.com> wrote:

> It appears that Sabahattin Gucukoglu  <listsebby@me.com> said:
>> If I'm honest, I'm just not a fan of code 556. If
>> somebody finds it useful, fair enough, but it seems to me to
>> require a special-case treatment of a non-existent domain,
>> which must be configured to be useful.
> 
> No, 556 doesn't need any special cases. The likely scenario is
> that you have a submission server, someone sends 
> 
>   RCPT TO:<someone@example.wtf> 
> 
> and the submission server sees that example.wtf has a null mx
> so it knows there's no point to accepting the mail. It doesn't
> need to look at the mailbox.  I suppose it would also be
> appropriate if the domain does not exist at all, again
> unrelated to the mailbox.
> 
> There's also 521 and 554 which say "I am not a mail server." I
> don't think that we can realistically change that to "I am not
> a mail server except that I can send postmaster mail
> somewhere."

Speaking personally, not as editor: John's "not a mail server
except that I accept mail for an address or two" would lead us
into all sorts of silly cases... and break the way things have
been specified since RFC 821.

Recent off-list correspondence leads me to believe that I see
more cases than John Levine did at the time I wrote him, but,
AFAICT, I can't see any special cases here.   If the SMTP server
knows that no mail is accepted but an attempt to open a mail
transaction is received anyway, 556 might reasonably be returned
at connection time.  As I read Section 4.2.4.2 of rfc5321bis-09
(and -10 -- any changes are not going to make it into that
version), 521 would be preferred if the SMTP server doesn't
figure out the it isn't accepting mail for that particular
domain until it gets a RCPT command, but 556 would be more
emphatic if the server were aware that there was a null MX
record for that domain and, speaking personally, I don't see
much value in trying to absolutely prohibit it for that case.

These things can get a tad more complicated if there is a
configuration inconsistency or misunderstand between the SMTP
server and the relevant authoritative DNS server/zone, but I
think the current text is robust against such problems.

Now, as editor, three requests/suggestions, the first for
Sabahattin and the other two for everyone:

(1) If, with John Levine's explanation and mine, you still don't
understand that this is not about special cases, please explain
what those cases are in a bit more detail.

(2) Please read Section 4.2.4.2, which is intended to cover all
of this, carefully.  If it still leaves loose ends or introduces
problems, please identify those as explicitly as possible and,
if possible suggest text or at least particular sentences that
need fixing.

(3) John Levine has pointed out that rfc5321bis-09 covers
substantially everything that is in RFC 7505 except the enhanced
status codes.   Especially given that we propose to obsolete
7505, should some words be added to that section to point to the
IANA registry with those codes in it?

thanks,
    john


From nobody Sat Mar  5 18:20:46 2022
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Date: Sat, 05 Mar 2022 21:20:31 -0500
From: John C Klensin <john-ietf@jck.com>
To: Alexey Melnikov <aamelnikov@fastmail.fm>, John R 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 Thursday, February 17, 2022 14:25 +0000 Alexey Melnikov
<aamelnikov@fastmail.fm> wrote:

> Hi John/John,
> 
> On Sat, Jan 22, 2022, at 5:47 AM, John C Klensin wrote:
>> --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?
> 
> I still think that the replacement text proposed at the
> interim is better than taking this sentence out, but I am
> happy with either:
> 
>   This change to MAIL FROM doesn't affect the header section
> of the message.

It seems to me that, after the interim and the subsequent
discussion, we have multiple options.  In no particular order:

(1) Leave the RFC 5321 text (in Section 3.9 there and Section
3.4.2 of 5321bis-10 (forthcoming) unchanged.  In the latter,
that sentence reads:

	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.

(2) Remove that sentence and replace it with nothing.

(3) Replace that sentence with 

	This change to MAIL FROM doesn't affect the header
	section of the message.

(4) Replace the sentence with something like

	This change to MAIL FROM does not affect any header that
	is already present in the message.

For the last two options, I'm not sure whether we are agreed on
the descriptive "does not" or if we intend a normative MUST or
SHOULD.

I've added a note to the working copy of -10 flagging this.

Alexey, please see my separate comments about untangling the
tickets that interact with that Section.

best,
   john


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Subject: Re: [Emailcore] 5321bis-09: Thinking About Interaction of Code 556 with 'postmaster'
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On 6 Mar 2022, at 02:19, John C Klensin <john-ietf@jck.com> wrote:
> --On Monday, February 21, 2022 14:10 -0500 John Levine
> <johnl@taugh.com> wrote:
>> It appears that Sabahattin Gucukoglu  <listsebby@me.com> said:
>>> If I'm honest, I'm just not a fan of code 556. If
>>> somebody finds it useful, fair enough, but it seems to me to
>>> require a special-case treatment of a non-existent domain,
>>> which must be configured to be useful.
>>=20
>> No, 556 doesn't need any special cases. The likely scenario is
>> that you have a submission server, someone sends=20
>>=20
>>  RCPT TO:<someone@example.wtf>=20
>>=20
>> and the submission server sees that example.wtf has a null mx
>> so it knows there's no point to accepting the mail. It doesn't
>> need to look at the mailbox.  I suppose it would also be
>> appropriate if the domain does not exist at all, again
>> unrelated to the mailbox.
>>=20
>> There's also 521 and 554 which say "I am not a mail server." I
>> don't think that we can realistically change that to "I am not
>> a mail server except that I can send postmaster mail
>> somewhere."
>=20
> Speaking personally, not as editor: John's "not a mail server
> except that I accept mail for an address or two" would lead us
> into all sorts of silly cases... and break the way things have
> been specified since RFC 821.

Accepted, absolutely. I do not propose to make the cost of refusing all =
mail prohibitive and it would be burdensome and unnecessary to require a =
server intended to refuse all mail to accept mail just for postmaster.

And yes, if a non-public intermediate or submission server performs =
checks in real time on mail being submitted against destination MXs or =
mailboxes then it can obviously be expected to informatively explain to =
the client that the destination domain is unreachable and no further =
configuration is necessary to achieve that effect. (I expect that many =
submission servers will refuse to do this for policy reasons, though, or =
to support submission clients or users that react poorly to failed =
submissions.)

> Recent off-list correspondence leads me to believe that I see
> more cases than John Levine did at the time I wrote him, but,
> AFAICT, I can't see any special cases here.   If the SMTP server
> knows that no mail is accepted but an attempt to open a mail
> transaction is received anyway, 556 might reasonably be returned
> at connection time.  As I read Section 4.2.4.2 of rfc5321bis-09
> (and -10 -- any changes are not going to make it into that
> version), 521 would be preferred if the SMTP server doesn't
> figure out the it isn't accepting mail for that particular
> domain until it gets a RCPT command, but 556 would be more
> emphatic if the server were aware that there was a null MX
> record for that domain and, speaking personally, I don't see
> much value in trying to absolutely prohibit it for that case.

OK, I re-read section 4.2.4.2 and RFCs 7504-5 and think I see what=E2=80=99=
s happened. If it is intended that 556 is used at connection-opening =
time on a public host then, firstly, I think section 4.2.4.2 needs a bit =
of work because the juxtaposition of the discussion of code 521 at =
connection-opening time (first paragraph) and the discussion of code 556 =
in intermediate system, submission and =E2=80=9Cthe server domain=E2=80=9D=
 as well (second paragraph) makes it all but inevitable that people like =
me will erroneously think the latter paragraph is only concerning a =
post-RCPT response by implication (which, incidentally, is not indicated =
in section 4.3.2 where as its use in connection establishment was and I =
clearly missed it) and, secondly, I would agree that no harm was done in =
that case.

Now, if after this explanation of my error in comprehension, there is =
still any relevance to public non-submission SMTP hosts (which might =
include intermediate systems that permit relay to certain destinations, =
but which are always configured as an MX target for domains for which =
they are responsible), I believe what we are left with is the question =
of whether it is proper to refuse mail at RCPT time with code 556. I =
would, I think, remain against =E2=80=94 it seems to me that any MTA =
capable of, in theory, receiving any mail for local mailbox storage or =
onward transmission to a mailbox store elsewhere ought in principle to =
receive postmaster mail for any of its domains, whether MX targets or =
A/AAAA implicit-MX targets or address-literal targets. To refuse mail =
with code 556 at RCPT time would require the public MX to know about a =
domain for which it did not receive mail, including postmaster mail, and =
would in effect be a special case for the refusal of mail for =
postmaster. Code 556 in response to RCPT should therefore only ever be =
used on submission servers or intermediate servers used internally for =
onward transmission for a restricted set of clients, i.e. which are not =
public servers that restrict mail acceptance to a fixed set of =
configured destinations and which could therefore be expected to perform =
MX lookups for unknown destination domains and react to NULL MX records, =
IMO. But, if that is thought overly disciplinarian, I am quite happy to =
see the consensus go the other way =E2=80=94 though I do think it would =
undermine the case for =E2=80=98postmaster=E2=80=99. My reading of RFCs =
7504-5 do not leave me with any doubt that code 556 is not relevant on a =
public MX post-RCPT, and the error in interpreting 5321bis is all mine =
in that regard. If so, then a little clarity to that effect in section =
4.2.4.2 is all that=E2=80=99s required.

> These things can get a tad more complicated if there is a
> configuration inconsistency or misunderstand between the SMTP
> server and the relevant authoritative DNS server/zone, but I
> think the current text is robust against such problems.

Agreed completely.

> Now, as editor, three requests/suggestions, the first for
> Sabahattin and the other two for everyone:
>=20
> (1) If, with John Levine's explanation and mine, you still don't
> understand that this is not about special cases, please explain
> what those cases are in a bit more detail.

If code 556 is relevant post-RCPT on a public MX host, it must be =
configured to refuse mail destined for an =E2=80=9Cunserviced=E2=80=9D =
domain, as above, otherwise it would normally just refuse to relay mail =
for policy reasons for domains it didn=E2=80=99t know about, or refuse =
mail for unknown mailboxes for domains it did.

> (2) Please read Section 4.2.4.2, which is intended to cover all
> of this, carefully.  If it still leaves loose ends or introduces
> problems, please identify those as explicitly as possible and,
> if possible suggest text or at least particular sentences that
> need fixing.

Code 556 should be explicitly called out as being valid at =
connection-opening in section 4.2.4.2; it shouldn=E2=80=99t be left to =
the command-reply sequences list. I think 5321bis is relevant to code =
556 post-RCPT and this needs to be clarified; even though 5321bis =
doesn=E2=80=99t pertain to submission, it does concern intermediate =
systems, which include SMTP relays used in a trusted environment, =
therefore the command-reply sequence list needs to acknowledge 556 as a =
possible reply to RCPT. Finally, we need a discussion of whether code =
556 post-RCPT on a public MX is appropriate at all, and to add text =
accordingly.

I hope this clarifies my thinking.

Cheers,
Sabahattin


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From: "John Levine" <johnl@taugh.com>
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Subject: Re: [Emailcore] 5321bis-09: Thinking About Interaction of Code 556 with 'postmaster'
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It appears that Sabahattin Gucukoglu  <listsebby@me.com> said:
>And yes, if a non-public intermediate or submission server performs checks in real time on mail being submitted
>against destination MXs or mailboxes then it can obviously be expected to informatively explain to the client that the
>destination domain is unreachable and no further configuration is necessary to achieve that effect. (I expect that
>many submission servers will refuse to do this for policy reasons, though, or to support submission clients or users
>that react poorly to failed submissions.)

Given a choice between rejecting at submission time and a bounce
later, I'll take the reject. In my experience MUAs don't do a fabulous
job of explaining the failure, but it's better than trying to figure
out a bounce.  This is the most likely scenario for 556.

>If code 556 is relevant post-RCPT on a public MX host, it must be configured to refuse mail destined for an
>“unserviced” domain, as above, otherwise it would normally just refuse to relay mail for policy reasons for
>domains it didn’t know about, or refuse mail for unknown mailboxes for domains it did.

I'm with you. An MTA is either configured to accept mail for a domain
or it isn't, and it's not likely to provide helpful opinions about the
ones it's not configured for.

I can imagine some arcane edge cases like an MTA set up as a secondary for a null MX, but now we're
into "don't do that" territory.

blah.wtf. MX 0 .
          MX 10 secondary.wtf.  <-- that one might give a 556, maybe

R's,
John


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Subject: Re: [Emailcore] 5321bis-09: Thinking About Interaction of Code 556 with 'postmaster'
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On 7 Mar 2022, at 02:59, John Levine <johnl@taugh.com> wrote:
> It appears that Sabahattin Gucukoglu  <listsebby@me.com> said:
>> If code 556 is relevant post-RCPT on a public MX host, it must be =
configured to refuse mail destined for an
>> =E2=80=9Cunserviced=E2=80=9D domain, as above, otherwise it would =
normally just refuse to relay mail for policy reasons for
>> domains it didn=E2=80=99t know about, or refuse mail for unknown =
mailboxes for domains it did.
>=20
> I'm with you. An MTA is either configured to accept mail for a domain
> or it isn't, and it's not likely to provide helpful opinions about the
> ones it's not configured for.

Agreed.

> I can imagine some arcane edge cases like an MTA set up as a secondary =
for a null MX, but now we're
> into "don't do that" territory.
>=20
> blah.wtf. MX 0 .
>          MX 10 secondary.wtf.  <-- that one might give a 556, maybe

I remember when it was trendy to allow yourself to be a backup MX for =
anybody who wanted to use your services; you=E2=80=99d check the MX list =
to see if you were a non-primary MX for the recipient domain and accept =
and queue the mail if you were. I don=E2=80=99t know anyone doing that =
in 2022 because it would make your reputation harder to protect from =
complete strangers using your system to contact others on their behalf =
or to inject forged mail for subsequent bouncing to a victim, but just =
in case, I suppose we could distinguish between =E2=80=9Cconfigured=E2=80=9D=
 and =E2=80=9Cunconfigured=E2=80=9D (or similar) domains for the =
purposes of the description of code 556 if that was still thought =
useful.

Cheers,
Sabahattin


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Date: Mon, 07 Mar 2022 10:52:56 +0000
From: "Alexey Melnikov" <aamelnikov@fastmail.fm>
To: "John C Klensin" <john-ietf@jck.com>
Cc: "John R Levine" <johnl@taugh.com>, emailcore@ietf.org
Content-Type: text/plain
Archived-At: <https://mailarchive.ietf.org/arch/msg/emailcore/G1jtHEvmL3rbE3azE6rBiMENAgo>
Subject: Re: [Emailcore] Post-Interim question about Section 3.4.2 of draft-ietf-emailcore-rfc5321bis-08
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Hi John,

Replying below as a participant:

On Sun, Mar 6, 2022, at 2:20 AM, John C Klensin wrote:
> --On Thursday, February 17, 2022 14:25 +0000 Alexey Melnikov
> <aamelnikov@fastmail.fm> wrote:
>
>> Hi John/John,
>> 
>> On Sat, Jan 22, 2022, at 5:47 AM, John C Klensin wrote:
>>> --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?
>> 
>> I still think that the replacement text proposed at the
>> interim is better than taking this sentence out, but I am
>> happy with either:
>> 
>>   This change to MAIL FROM doesn't affect the header section
>> of the message.
>
> It seems to me that, after the interim and the subsequent
> discussion, we have multiple options.  In no particular order:
>
> (1) Leave the RFC 5321 text (in Section 3.9 there and Section
> 3.4.2 of 5321bis-10 (forthcoming) unchanged.  In the latter,
> that sentence reads:
>
> 	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.
>
> (2) Remove that sentence and replace it with nothing.
>
> (3) Replace that sentence with 
>
> 	This change to MAIL FROM doesn't affect the header
> 	section of the message.
>
> (4) Replace the sentence with something like
>
> 	This change to MAIL FROM does not affect any header that
> 	is already present in the message.

Did you mean "header" or "header field"?

> For the last two options, I'm not sure whether we are agreed on
> the descriptive "does not" or if we intend a normative MUST or
> SHOULD.

Either of the last 2 work for me. I don't think we need normative language in either case.

>
> I've added a note to the working copy of -10 flagging this.
>
> Alexey, please see my separate comments about untangling the
> tickets that interact with that Section.


Best Regards,
Alexey


From nobody Mon Mar  7 05:01:32 2022
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Date: Mon, 7 Mar 2022 14:01:05 +0100
From: Toerless Eckert <tte@cs.fau.de>
To: emailcore@ietf.org
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Subject: [Emailcore] How to send email to user@gmail.com ?
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Sorry to send a question to the list that is purely operational in nature,
but i wouldn't know a better list to ask such as question.
if gmail was not free, they wouldn't answe...

Since a few weeks ? I am having more and more trouble to do IETF work because
many colleagues i need to send email to have gmail accounts, and i am more and
more often getting the error message below from gmail, and the URL that google
points to has the whole kitchen sink of possible anti-spam precautions that
gmail seemingly would like to offload to senders of email. Which seems to me
like a nice abuse of market power on behalv of gmail. That email was just a test
email i sent to my own gmail account. And interestingly, the first email i sent made it through
to my mailbox, and when i sent an email again a few minutes later it failed.

Oh: bonus question: Any recommendations for another email service to use instead of gmail ?
(this is not the only problem i encountered, gmail also announced they are shutting down
 supposedly "insecure" access to sending mail, so i can not even send emails from my
 service provider installed home router...).

Thanks & cheers
    Toerless

In-Reply-To: <20220307125430.2FC51549A2E@faui40.informatik.uni-erlangen.de>

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> Date: Mon, 7 Mar 2022 13:54:27 +0100
> From: Toerless Eckert <tte@cs.fau.de>
> To: toerless.eckert@gmail.com
> Subject: Test 2 from tte@cs.fau.de
> 
> 
> -- 
> ---
> tte@cs.fau.de


-- 
---
tte@cs.fau.de


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Date: Mon, 07 Mar 2022 07:56:19 -0800
From: "Bron Gondwana" <brong@fastmailteam.com>
To: "Toerless Eckert" <tte@cs.fau.de>, emailcore@ietf.org
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Subject: Re: [Emailcore] How to send email to user@gmail.com ?
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--13e435a798d84a33ac77e8ece792eb94
Content-Type: text/plain

Sounds like your sending host doesn't have DKIM and/or SPF, or it's set up incorrectly.  You'll have issues with a lot more than just gmail.

You appear to be sending via IPV6.  Are your connections coming from inside the range `2001:638:a000::/48` ?  Also, are your emails DKIM signed?

Gmail is significantly more strict about authentication for mail over IPv6.  I see that your sending domain doesn't provide a DMARC record, so this could be the issue since it's sending over IPV6.

And yes, "supposedly insecure" is flat out insecure - there's no way to authenticate that your home router isn't somebody else's home router in the general sense.

Regards,

Bron.

On Mon, Mar 7, 2022, at 05:01, Toerless Eckert wrote:
> Sorry to send a question to the list that is purely operational in nature,
> but i wouldn't know a better list to ask such as question.
> if gmail was not free, they wouldn't answe...
> 
> Since a few weeks ? I am having more and more trouble to do IETF work because
> many colleagues i need to send email to have gmail accounts, and i am more and
> more often getting the error message below from gmail, and the URL that google
> points to has the whole kitchen sink of possible anti-spam precautions that
> gmail seemingly would like to offload to senders of email. Which seems to me
> like a nice abuse of market power on behalv of gmail. That email was just a test
> email i sent to my own gmail account. And interestingly, the first email i sent made it through
> to my mailbox, and when i sent an email again a few minutes later it failed.
> 
> Oh: bonus question: Any recommendations for another email service to use instead of gmail ?
> (this is not the only problem i encountered, gmail also announced they are shutting down
> supposedly "insecure" access to sending mail, so i can not even send emails from my
> service provider installed home router...).
> 
> Thanks & cheers
>     Toerless
> 
> In-Reply-To: <20220307125430.2FC51549A2E@faui40.informatik.uni-erlangen.de>
> 
> On Mon, Mar 07, 2022 at 01:54:30PM +0100, Mail Delivery System wrote:
> > This is the mail system at host faui40.informatik.uni-erlangen.de.
> > 
> > I'm sorry to have to inform you that your message could not
> > be delivered to one or more recipients. It's attached below.
> > 
> > For further assistance, please send mail to postmaster.
> > 
> > If you do so, please include this problem report. You can
> > delete your own text from the attached returned message.
> > 
> >                    The mail system
> > 
> > <toerless.eckert@gmail.com>: host
> >     gmail-smtp-in.l.google.com[2a00:1450:400c:c0a::1a] said: 550-5.7.26 This
> >     message does not have authentication information or fails to 550-5.7.26
> >     pass authentication checks. To best protect our users from spam, the
> >     550-5.7.26 message has been blocked. Please visit 550-5.7.26
> >     https://support.google.com/mail/answer/81126#authentication for more 550
> >     5.7.26 information. n13-20020a056000170d00b001f1eb289340si4396727wrc.790 -
> >     gsmtp (in reply to end of DATA command)
> 
> > Reporting-MTA: dns; faui40.informatik.uni-erlangen.de
> > X-Postfix-Queue-ID: 48F455499E9
> > X-Postfix-Sender: rfc822; eckert@i4.informatik.uni-erlangen.de
> > Arrival-Date: Mon,  7 Mar 2022 13:54:27 +0100 (CET)
> > 
> > Final-Recipient: rfc822; toerless.eckert@gmail.com
> > Original-Recipient: rfc822;toerless.eckert@gmail.com
> > Action: failed
> > Status: 5.7.26
> > Remote-MTA: dns; gmail-smtp-in.l.google.com
> > Diagnostic-Code: smtp; 550-5.7.26 This message does not have authentication
> >     information or fails to 550-5.7.26 pass authentication checks. To best
> >     protect our users from spam, the 550-5.7.26 message has been blocked.
> >     Please visit 550-5.7.26
> >     https://support.google.com/mail/answer/81126#authentication for more 550
> >     5.7.26 information. n13-20020a056000170d00b001f1eb289340si4396727wrc.790 -
> >     gsmtp
> 
> > Date: Mon, 7 Mar 2022 13:54:27 +0100
> > From: Toerless Eckert <tte@cs.fau.de>
> > To: toerless.eckert@gmail.com
> > Subject: Test 2 from tte@cs.fau.de
> > 
> > 
> > -- 
> > ---
> > tte@cs.fau.de
> 
> 
> -- 
> ---
> tte@cs.fau.de
> 
> -- 
> Emailcore mailing list
> Emailcore@ietf.org
> https://www.ietf.org/mailman/listinfo/emailcore
> 

--
  Bron Gondwana, CEO, Fastmail Pty Ltd
  brong@fastmailteam.com


--13e435a798d84a33ac77e8ece792eb94
Content-Type: text/html
Content-Transfer-Encoding: quoted-printable

<!DOCTYPE html><html><head><title></title><style type=3D"text/css">p.Mso=
Normal,p.MsoNoSpacing{margin:0}</style></head><body><div style=3D"font-f=
amily:Arial;">Sounds like your sending host doesn't have DKIM and/or SPF=
, or it's set up incorrectly.&nbsp; You'll have issues with a lot more t=
han just gmail.<br></div><div style=3D"font-family:Arial;"><br></div><di=
v style=3D"font-family:Arial;">You appear to be sending via IPV6.&nbsp; =
Are your connections coming from inside the range <span id=3D"lblResult"=
><code style=3D"border-top-color:rgb(204, 204, 204);border-top-style:sol=
id;border-top-width:1px;border-right-color:rgb(204, 204, 204);border-rig=
ht-style:solid;border-right-width:1px;border-bottom-color:rgb(204, 204, =
204);border-bottom-style:solid;border-bottom-width:1px;border-left-color=
:rgb(204, 204, 204);border-left-style:solid;border-left-width:1px;border=
-image-outset:0;border-image-repeat:stretch;border-image-slice:100%;bord=
er-image-source:none;border-image-width:1;border-top-left-radius:3px;bor=
der-top-right-radius:3px;border-bottom-right-radius:3px;border-bottom-le=
ft-radius:3px;background-color:rgb(246, 246, 246);background-position-x:=
0%;background-position-y:0%;background-repeat:repeat;background-attachme=
nt:scroll;background-image:none;background-size:auto;background-origin:p=
adding-box;background-clip:border-box;font-family:menlo, consolas, monos=
pace;font-size:90%;padding-top:1px;padding-right:3px;padding-bottom:1px;=
padding-left:3px;">2001:638:a000::/48</code> ?&nbsp; Also, are your emai=
ls DKIM signed?</span><br></div><div style=3D"font-family:Arial;"><br></=
div><div style=3D"font-family:Arial;"><span id=3D"lblResult">Gmail is si=
gnificantly more strict about authentication for mail over IPv6.&nbsp; I=
 see that your sending domain doesn't provide a DMARC record, so this co=
uld be the issue since it's sending over IPV6.</span><br></div><div styl=
e=3D"font-family:Arial;"><br></div><div style=3D"font-family:Arial;"><sp=
an id=3D"lblResult">And yes, "supposedly insecure" is flat out insecure =
- there's no way to authenticate that your home router isn't somebody el=
se's home router in the general sense.</span><br></div><div style=3D"fon=
t-family:Arial;"><br></div><div style=3D"font-family:Arial;"><span id=3D=
"lblResult">Regards,</span><br></div><div style=3D"font-family:Arial;"><=
span id=3D"lblResult"><br>Bron.</span><br></div><div style=3D"font-famil=
y:Arial;"><br></div><div>On Mon, Mar 7, 2022, at 05:01, Toerless Eckert =
wrote:<br></div><blockquote type=3D"cite" id=3D"qt" style=3D""><div styl=
e=3D"font-family:Arial;">Sorry to send a question to the list that is pu=
rely operational in nature,<br></div><div style=3D"font-family:Arial;">b=
ut i wouldn't know a better list to ask such as question.<br></div><div =
style=3D"font-family:Arial;">if gmail was not free, they wouldn't answe.=
..<br></div><div style=3D"font-family:Arial;"><br></div><div style=3D"fo=
nt-family:Arial;">Since a few weeks ? I am having more and more trouble =
to do IETF work because<br></div><div style=3D"font-family:Arial;">many =
colleagues i need to send email to have gmail accounts, and i am more an=
d<br></div><div style=3D"font-family:Arial;">more often getting the erro=
r message below from gmail, and the URL that google<br></div><div style=3D=
"font-family:Arial;">points to has the whole kitchen sink of possible an=
ti-spam precautions that<br></div><div style=3D"font-family:Arial;">gmai=
l seemingly would like to offload to senders of email. Which seems to me=
<br></div><div style=3D"font-family:Arial;">like a nice abuse of market =
power on behalv of gmail. That email was just a test<br></div><div style=
=3D"font-family:Arial;">email i sent to my own gmail account. And intere=
stingly, the first email i sent made it through<br></div><div style=3D"f=
ont-family:Arial;">to my mailbox, and when i sent an email again a few m=
inutes later it failed.<br></div><div style=3D"font-family:Arial;"><br><=
/div><div style=3D"font-family:Arial;">Oh: bonus question: Any recommend=
ations for another email service to use instead of gmail ?<br></div><div=
 style=3D"font-family:Arial;">(this is not the only problem i encountere=
d, gmail also announced they are shutting down<br></div><div style=3D"fo=
nt-family:Arial;">supposedly "insecure" access to sending mail, so i can=
 not even send emails from my<br></div><div style=3D"font-family:Arial;"=
>service provider installed home router...).<br></div><div style=3D"font=
-family:Arial;"><br></div><div style=3D"font-family:Arial;">Thanks &amp;=
 cheers<br></div><div style=3D"font-family:Arial;">&nbsp;&nbsp;&nbsp; To=
erless<br></div><div style=3D"font-family:Arial;"><br></div><div style=3D=
"font-family:Arial;">In-Reply-To: &lt;<a href=3D"mailto:20220307125430.2=
FC51549A2E@faui40.informatik.uni-erlangen.de">20220307125430.2FC51549A2E=
@faui40.informatik.uni-erlangen.de</a>&gt;<br></div><div style=3D"font-f=
amily:Arial;"><br></div><div style=3D"font-family:Arial;">On Mon, Mar 07=
, 2022 at 01:54:30PM +0100, Mail Delivery System wrote:<br></div><div st=
yle=3D"font-family:Arial;">&gt; This is the mail system at host faui40.i=
nformatik.uni-erlangen.de.<br></div><div style=3D"font-family:Arial;">&g=
t;&nbsp;<br></div><div style=3D"font-family:Arial;">&gt; I'm sorry to ha=
ve to inform you that your message could not<br></div><div style=3D"font=
-family:Arial;">&gt; be delivered to one or more recipients. It's attach=
ed below.<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;<br></div=
><div style=3D"font-family:Arial;">&gt; For further assistance, please s=
end mail to postmaster.<br></div><div style=3D"font-family:Arial;">&gt;&=
nbsp;<br></div><div style=3D"font-family:Arial;">&gt; If you do so, plea=
se include this problem report. You can<br></div><div style=3D"font-fami=
ly:Arial;">&gt; delete your own text from the attached returned message.=
<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;<br></div><div sty=
le=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;=
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;=
 The mail system<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;<b=
r></div><div style=3D"font-family:Arial;">&gt; &lt;<a href=3D"mailto:toe=
rless.eckert@gmail.com">toerless.eckert@gmail.com</a>&gt;: host<br></div=
><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; gmail-sm=
tp-in.l.google.com[2a00:1450:400c:c0a::1a] said: 550-5.7.26 This<br></di=
v><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; message=
 does not have authentication information or fails to 550-5.7.26<br></di=
v><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; pass au=
thentication checks. To best protect our users from spam, the<br></div><=
div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; 550-5.7.26=
 message has been blocked. Please visit 550-5.7.26<br></div><div style=3D=
"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<a href=3D"https:=
//support.google.com/mail/answer/81126#authentication">https://support.g=
oogle.com/mail/answer/81126#authentication</a> for more 550<br></div><di=
v style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; 5.7.26 infor=
mation. n13-20020a056000170d00b001f1eb289340si4396727wrc.790 -<br></div>=
<div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; gsmtp (in=
 reply to end of DATA command)<br></div><div style=3D"font-family:Arial;=
"><br></div><div style=3D"font-family:Arial;">&gt; Reporting-MTA: dns; f=
aui40.informatik.uni-erlangen.de<br></div><div style=3D"font-family:Aria=
l;">&gt; X-Postfix-Queue-ID: 48F455499E9<br></div><div style=3D"font-fam=
ily:Arial;">&gt; X-Postfix-Sender: rfc822;&nbsp;<a href=3D"mailto:eckert=
@i4.informatik.uni-erlangen.de">eckert@i4.informatik.uni-erlangen.de</a>=
<br></div><div style=3D"font-family:Arial;">&gt; Arrival-Date: Mon,&nbsp=
; 7 Mar 2022 13:54:27 +0100 (CET)<br></div><div style=3D"font-family:Ari=
al;">&gt;&nbsp;<br></div><div style=3D"font-family:Arial;">&gt; Final-Re=
cipient: rfc822;&nbsp;<a href=3D"mailto:toerless.eckert@gmail.com">toerl=
ess.eckert@gmail.com</a><br></div><div style=3D"font-family:Arial;">&gt;=
 Original-Recipient: rfc822;<a href=3D"mailto:toerless.eckert@gmail.com"=
>toerless.eckert@gmail.com</a><br></div><div style=3D"font-family:Arial;=
">&gt; Action: failed<br></div><div style=3D"font-family:Arial;">&gt; St=
atus: 5.7.26<br></div><div style=3D"font-family:Arial;">&gt; Remote-MTA:=
 dns; gmail-smtp-in.l.google.com<br></div><div style=3D"font-family:Aria=
l;">&gt; Diagnostic-Code: smtp; 550-5.7.26 This message does not have au=
thentication<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;=
&nbsp;&nbsp; information or fails to 550-5.7.26 pass authentication chec=
ks. To best<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&=
nbsp;&nbsp; protect our users from spam, the 550-5.7.26 message has been=
 blocked.<br></div><div style=3D"font-family:Arial;">&gt;&nbsp;&nbsp;&nb=
sp;&nbsp; Please visit 550-5.7.26<br></div><div style=3D"font-family:Ari=
al;">&gt;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<a href=3D"https://support.google=
.com/mail/answer/81126#authentication">https://support.google.com/mail/a=
nswer/81126#authentication</a> for more 550<br></div><div style=3D"font-=
family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; 5.7.26 information. n13-2002=
0a056000170d00b001f1eb289340si4396727wrc.790 -<br></div><div style=3D"fo=
nt-family:Arial;">&gt;&nbsp;&nbsp;&nbsp;&nbsp; gsmtp<br></div><div style=
=3D"font-family:Arial;"><br></div><div style=3D"font-family:Arial;">&gt;=
 Date: Mon, 7 Mar 2022 13:54:27 +0100<br></div><div style=3D"font-family=
:Arial;">&gt; From: Toerless Eckert &lt;<a href=3D"mailto:tte@cs.fau.de"=
>tte@cs.fau.de</a>&gt;<br></div><div style=3D"font-family:Arial;">&gt; T=
o:&nbsp;<a href=3D"mailto:toerless.eckert@gmail.com">toerless.eckert@gma=
il.com</a><br></div><div style=3D"font-family:Arial;">&gt; Subject: Test=
 2 from&nbsp;<a href=3D"mailto:tte@cs.fau.de">tte@cs.fau.de</a><br></div=
><div style=3D"font-family:Arial;">&gt;&nbsp;<br></div><div style=3D"fon=
t-family:Arial;">&gt;&nbsp;<br></div><div style=3D"font-family:Arial;">&=
gt; --&nbsp;<br></div><div style=3D"font-family:Arial;">&gt; ---<br></di=
v><div style=3D"font-family:Arial;">&gt;&nbsp;<a href=3D"mailto:tte@cs.f=
au.de">tte@cs.fau.de</a><br></div><div style=3D"font-family:Arial;"><br>=
</div><div style=3D"font-family:Arial;"><br></div><div style=3D"font-fam=
ily:Arial;">--&nbsp;<br></div><div style=3D"font-family:Arial;">---<br><=
/div><div style=3D"font-family:Arial;"><a href=3D"mailto:tte@cs.fau.de">=
tte@cs.fau.de</a><br></div><div style=3D"font-family:Arial;"><br></div><=
div style=3D"font-family:Arial;">--&nbsp;<br></div><div style=3D"font-fa=
mily:Arial;">Emailcore mailing list<br></div><div style=3D"font-family:A=
rial;"><a href=3D"mailto:Emailcore@ietf.org">Emailcore@ietf.org</a><br><=
/div><div style=3D"font-family:Arial;"><a href=3D"https://www.ietf.org/m=
ailman/listinfo/emailcore">https://www.ietf.org/mailman/listinfo/emailco=
re</a><br></div><div style=3D"font-family:Arial;"><br></div></blockquote=
><div style=3D"font-family:Arial;"><br></div><div id=3D"sig56629417"><di=
v class=3D"signature">--<br></div><div class=3D"signature">&nbsp; Bron G=
ondwana, CEO, Fastmail Pty Ltd<br></div><div class=3D"signature">&nbsp; =
brong@fastmailteam.com<br></div><div class=3D"signature"><br></div></div=
><div style=3D"font-family:Arial;"><br></div></body></html>
--13e435a798d84a33ac77e8ece792eb94--


From nobody Mon Mar  7 08:41:18 2022
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Subject: Re: [Emailcore] How to send email to user@gmail.com ?
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On Mon, Mar 07, 2022, Toerless Eckert wrote:

> I am having more and more trouble to do IETF work because
> many colleagues i need to send email to have gmail accounts,

Maybe use the "matching" IETF mailing list, so it's their
server, not yours, which contacts gmail?

>  Which seems to me
> like a nice abuse of market power on behalv of gmail.

"We don't care, we don't have to, we are the phone company."

Agreed -- I am also getting more rejects even though I had
communicated with the same people before.

(No, I won't set up all the stuff that gmail requires...
it's more and more -- where/when will it stop?
- when you pay them money?)


-- 
Address is valid for this mailing list only, please do not reply
to it directly, but to the list.


From nobody Mon Mar  7 10:56:53 2022
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To: Alexey Melnikov <aamelnikov@fastmail.fm>
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--On Monday, March 7, 2022 10:52 +0000 Alexey Melnikov
<aamelnikov@fastmail.fm> wrote:

>...

>> It seems to me that, after the interim and the subsequent
>> discussion, we have multiple options.  In no particular order:

>> (1) Leave the RFC 5321 text (in Section 3.9 there and Section
>> 3.4.2 of 5321bis-10 (forthcoming) unchanged.  In the latter,
>> that sentence reads:
>> 
>> 	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.
>> 
>> (2) Remove that sentence and replace it with nothing.
>> 
>> (3) Replace that sentence with 
>> 
>> 	This change to MAIL FROM doesn't affect the header
>> 	section of the message.
>> 
>> (4) Replace the sentence with something like
>> 
>> 	This change to MAIL FROM does not affect any header that
>> 	is already present in the message.
> 
> Did you mean "header" or "header field"?

"Header field".  I should not compose messages at 2AM.

>> For the last two options, I'm not sure whether we are agreed
>> on the descriptive "does not" or if we intend a normative
>> MUST or SHOULD.
> 
> Either of the last 2 work for me. I don't think we need
> normative language in either case.

Concur.  Anyone who has a strong preference, or who wants to
argue for either of the first two, should speak up.  Otherwise,
I will likely use (4) because, as John Levine suggested, (3)
could be read as prohibiting adding additional header fields.
I'm not sure that is an important case, but there is no reason
to leave confusion about whether it would be prohibited or not.

>> I've added a note to the working copy of -10 flagging this.

Barring more interruptions, -10 should be posted with the hour.

thanks,
   john


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Subject: [Emailcore] draft-ietf-emailcore-rfc5321bis-10
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EMAILCORE WG,

As promised (threatened?) -10 is now in the posting queue and
will, I assume, appear RSN.

It contains few substantive changes since -09, partially because
I got very busy in the interim but more because few of the
issues that came up before or during the Interim have been
unambiguously resolved since then (as some postings within the
last 24 hours make clear).   I have done some future cleaning
up, inserted or revised notes to further clarify the issues or
alternatives, and left notes to myself (ones that you won't see)
that will make it easier to fix the text for some issues once
they are resolved.  I've also made a pass through the tickets to
see if I could improve the alignment between that list and the
document (and, I hope, gotten that right).

As usual, there is an Appendix, H.3.14 in this version, that
gives a more detailed description of changes. 

Happy reading.
    john


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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           : Simple Mail Transfer Protocol
        Author          : John C. Klensin
	Filename        : draft-ietf-emailcore-rfc5321bis-10.txt
	Pages           : 125
	Date            : 2022-03-07

Abstract:
   This document is a specification of the basic protocol for Internet
   electronic mail transport.  It (including text carried forward from
   RFC 5321) consolidates, updates, and clarifies several previous
   documents, making all or parts of most of them obsolete.  It covers
   the SMTP extension mechanisms and best practices for the contemporary
   Internet, but does not provide details about particular extensions.
   The document also provides information about use of SMTP for other
   than strict mail transport and delivery.  This document replaces RFC
   5321, the earlier version with the same title.


The IETF datatracker status page for this draft is:
https://datatracker.ietf.org/doc/draft-ietf-emailcore-rfc5321bis/

There is also an htmlized version available at:
https://datatracker.ietf.org/doc/html/draft-ietf-emailcore-rfc5321bis-10

A diff from the previous version is available at:
https://www.ietf.org/rfcdiff?url2=draft-ietf-emailcore-rfc5321bis-10


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



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Subject: Re: [Emailcore] How to send email to user@gmail.com ?
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> Since a few weeks ? I am having more and more trouble to do IETF work because
> many colleagues i need to send email to have gmail accounts, and i am more and
> more often getting the error message below from gmail, ...

They have been tightening up their validation rules.  Your SPF record 
seems to be OK but I agree that DKIM signing is likely to help a lot.

> Oh: bonus question: Any recommendations for another email service to use instead of gmail ?

If you want a free mail provider, you get what you pay for.  Among paid 
providers, Fastmail has a good reputation and Bron would never tout his 
own service.

> (this is not the only problem i encountered, gmail also announced they are shutting down
> supposedly "insecure" access to sending mail, so i can not even send emails from my
> service provider installed home router...).

To send mail through Gmail you need to authenticate with oauth.  This is 
tedious but it does work. I set up my gmail account in my copy of Alpine 
yesterday.

Regards,
John Levine, johnl@taugh.com, Primary Perpetrator of "The Internet for Dummies",
Please consider the environment before reading this e-mail. https://jl.ly


From nobody Mon Mar  7 14:22:47 2022
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John R. Levine wrote in

[I left you off To:, right.  I hate that bouncing.]

 <7dc816a9-cacd-4207-2e72-0e17b61cdd49@iecc.com>:
 |> Since a few weeks ? I am having more and more trouble to do IETF \
 |> work because
 |> many colleagues i need to send email to have gmail accounts, and \
 |> i am more and
 |> more often getting the error message below from gmail, ...
 |
 |They have been tightening up their validation rules.  Your SPF record 
 |seems to be OK but I agree that DKIM signing is likely to help a lot.
 ...
 |> (this is not the only problem i encountered, gmail also announced \
 |> they are shutting down
 |> supposedly "insecure" access to sending mail, so i can not even send \
 |> emails from my
 |> service provider installed home router...).
 |
 |To send mail through Gmail you need to authenticate with oauth.  This is 
 |tedious but it does work. I set up my gmail account in my copy of Alpine 
 |yesterday.

You can use 2-factor with an application-specific password, and
that works with authentication schemes which do not need JSON and
HTTP 1/[2/3] and a browser (but for setup).

I hope they do not shut that down?

--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)


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Subject: Re: [Emailcore] How to send email to user@gmail.com ?
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Steffen Nurpmeso wrote in
 <20220307222221.w_fAY%steffen@sdaoden.eu>:
 |John R. Levine wrote in
 | <7dc816a9-cacd-4207-2e72-0e17b61cdd49@iecc.com>:
 ||> Since a few weeks ? I am having more and more trouble to do IETF \
 ||> work because
 ||> many colleagues i need to send email to have gmail accounts, and \
 ||> i am more and
 ||> more often getting the error message below from gmail, ...
 ||
 ||They have been tightening up their validation rules.  Your SPF record 
 ||seems to be OK but I agree that DKIM signing is likely to help a lot.
 | ...
 ||> (this is not the only problem i encountered, gmail also announced \
 ||> they are shutting down
 ||> supposedly "insecure" access to sending mail, so i can not even send \
 ||> emails from my
 ||> service provider installed home router...).
 ||
 ||To send mail through Gmail you need to authenticate with oauth.  This is 
 ||tedious but it does work. I set up my gmail account in my copy of Alpine 
 ||yesterday.
 |
 |You can use 2-factor with an application-specific password, and
 |that works with authentication schemes which do not need JSON and
 |HTTP 1/[2/3] and a browser (but for setup).

Not to mention that it seems impossible to get an OAUTH "client
secret" (?) for a normal console based application at GMail.

 |I hope they do not shut that down?

--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)


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From: "Murray S. Kucherawy" <superuser@gmail.com>
Date: Mon, 7 Mar 2022 19:47:33 -0800
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Subject: Re: [Emailcore] Should rfc5322bis register an Email Authentication Method to report overall format conformance?
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--00000000000004816505d9acd850
Content-Type: text/plain; charset="UTF-8"

On Sat, Mar 5, 2022 at 6:09 AM Alessandro Vesely <vesely@tana.it> wrote:

> perhaps I should have questioned ietf-822 about this idea.  However, since
> the
> standard is now being revised, perhaps it makes more sense to ask here
> directly.
>
> As is well known, RFC 8601 provides ways to describe the level of trust
> that a
> message is considered to deserve, according to a variety of methods, in an
> Authentication-Results: (A-R) header field.  Deep down, all methods rely
> on the
> mail format.  However, the format itself is not reported directly.
>
> For example, a popular DKIM filter has an option to refuse processing of a
> message if the header field count does not conform to RFC5322 Section 3.6.
> That stems from inconsistencies among different software about how to
> treat
> anomalies such as multiple From: fields, which can result in
> authenticating a
> field which is not the one displayed.[*]
>
> What to do in such cases?  The old message just exemplified[*] had a
> cryptographically correct A-R:
> [...]
>

Using an authentication reporting mechanism to indicate something about
compliance or format checking seems a lot like scope creep to me.

-MSK, with no particular hat on

--00000000000004816505d9acd850
Content-Type: text/html; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

<div dir=3D"ltr"><div dir=3D"ltr">On Sat, Mar 5, 2022 at 6:09 AM Alessandro=
 Vesely &lt;<a href=3D"mailto:vesely@tana.it">vesely@tana.it</a>&gt; wrote:=
<br></div><div class=3D"gmail_quote"><blockquote class=3D"gmail_quote" styl=
e=3D"margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);paddin=
g-left:1ex">perhaps I should have questioned ietf-822 about this idea.=C2=
=A0 However, since the <br>
standard is now being revised, perhaps it makes more sense to ask here dire=
ctly.<br>
<br>
As is well known, RFC 8601 provides ways to describe the level of trust tha=
t a <br>
message is considered to deserve, according to a variety of methods, in an =
<br>
Authentication-Results: (A-R) header field.=C2=A0 Deep down, all methods re=
ly on the <br>
mail format.=C2=A0 However, the format itself is not reported directly.<br>
<br>
For example, a popular DKIM filter has an option to refuse processing of a =
<br>
message if the header field count does not conform to RFC5322 Section 3.6. =
<br>
That stems from inconsistencies among different software about how to treat=
 <br>
anomalies such as multiple From: fields, which can result in authenticating=
 a <br>
field which is not the one displayed.[*]<br>
<br>
What to do in such cases?=C2=A0 The old message just exemplified[*] had a <=
br>
cryptographically correct A-R:<br>
[...]<br></blockquote><div><br></div>Using an authentication reporting mech=
anism to indicate something about compliance or format checking seems a lot=
 like scope creep to me.</div><div class=3D"gmail_quote"><br></div><div cla=
ss=3D"gmail_quote">-MSK, with no particular hat on<br></div></div>

--00000000000004816505d9acd850--


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Subject: Re: [Emailcore] Should rfc5322bis register an Email Authentication Method to report overall format conformance?
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It appears that Murray S. Kucherawy  <superuser@gmail.com> said:
>Using an authentication reporting mechanism to indicate something about
>compliance or format checking seems a lot like scope creep to me.

I don't know how to define a compliance metric and I'm pretty sure nobody else does, either.

For that and other reasons this is a complete non-starter.

[ replies directed to a list where this is slightly less off-topic ]

R's,
John


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--On Sunday, March 6, 2022 21:59 -0500 John Levine
<johnl@taugh.com> wrote:

> It appears that Sabahattin Gucukoglu  <listsebby@me.com> said:
>> And yes, if a non-public intermediate or submission server
>> performs checks in real time on mail being submitted against
>> destination MXs or mailboxes then it can obviously be
>> expected to informatively explain to the client that the
>> destination domain is unreachable and no further
>> configuration is necessary to achieve that effect. (I expect
>> that many submission servers will refuse to do this for
>> policy reasons, though, or to support submission clients or
>> users that react poorly to failed submissions.)

(no hat)

This is far out of scope for SMTP and hence 5321bis, but I have
trouble imagining why a submission server configuration would
feel a need to hide information about a destination domain
refusing to accept mail from the submitting client.  After all,
those two are supposed to have a close relationship.  The
submission server is not some random host on the network at
which the client lobs a message. RFC 5068/BCP 134 specifies that
it authenticate the client and RFC 8314 requires encryption.
>From the standpoint of a user sitting in front of that client,
the most likely cause of a 556 error is trying to use a bad
address, possibly the result of a typographical error and it is
in everyone's interest that such a problem be reported with an
appropriate level of clarity so that error can be corrected.
Now, I suppose that if one were running an open submission
server (sort of like an open relay), accepting traffic on port
25 rather than 587, the situation would be quite different.
But, to put it mildly, we don't consider running such servers to
be a good practice and have not for many years.

Now, if someone tells me that some of the very large mail
providers don't handle submission very well and hence needed to
obscure information to cover up their own failings, I guess I
would not be surprised.  However...

> Given a choice between rejecting at submission time and a
> bounce later, I'll take the reject. In my experience MUAs
> don't do a fabulous job of explaining the failure, but it's
> better than trying to figure out a bounce.  This is the most
> likely scenario for 556.

Agreed.

>> If code 556 is relevant post-RCPT on a public MX host, it
>> must be configured to refuse mail destined for an
>> "unserviced" domain, as above, otherwise it would
>> normally just refuse to relay mail for policy reasons for
>> domains it didn't know about, or refuse mail for unknown
>> mailboxes for domains it did.
> 
> I'm with you. An MTA is either configured to accept mail for a
> domain or it isn't, and it's not likely to provide helpful
> opinions about the ones it's not configured for.

For the vast majority of cases, I agree.  See below.
 
> I can imagine some arcane edge cases like an MTA set up as a
> secondary for a null MX, but now we're into "don't do that"
> territory.
> 
> blah.wtf. MX 0 .
>           MX 10 secondary.wtf.  <-- that one might give a 556,
> maybe

Right, but that would be so blatantly stupid that I assume that,
were it common, those who produce DNS software would be
considering adding it to their sanity test tools.   But let me
walk through a moderately complicated --but, IMO, plausible--
scenario because I'm no longer sure what 5321bis should say.
Consider the following with the understanding that this is
probably uncommon at best:

As I think I mentioned in another message, consider the
possibility of an enterprise, call it LittleCo, in which those
who maintain DNS records and those who maintain servers that
handle mail are in separate organizations.  It would be an
especially nasty case if one organization had outsourced, e.g.,
mail and web services to one provider (example1.net) but DNS
services to a different one (example2.net).  I gather that
occurs a lot (even if it would not pass for "common").   Also
assume that both example1.net and example2.net (and
example3.net, which I will get to in a moment), provide services
to multiple domains.  Skipping assorted possible complications
and using CNAME, not because it is a good idea but because it
makes the example shorter, we have, on the authoritative
example2.net:

   LittleCo.example.     IN CNAME example1.net.
   www.LittleCo.example. IN CNAME example1.net.
   LittleCo.example.     MX 0 example1.net.

Now, someone in the management of LittleCo decides that it does
not like the mail service being provided by example1.net and
wants to move it to example3.net.  They get the service set up
on example3.net and then  send out memos to the provider who
runs example1.net telling them that they no longer have a
contract to support mail for LittleCo and to LittleCo's DNS
provider telling them to change the MX RR.  If they are smart
and good negotiators, they get example1.net to host a relay for
a while, presumably several times the TTL, so the target DNS
structure during that period looks like:

   LittleCo.example.     IN CNAME example1.net.
   www.LittleCo.example. IN CNAME example1.net.
   LittleCo.example.     MX 10 example1.net.
   LittleCo.example.     MX 0 example3.net.

If those changes do not occur in the right order and with some
luck, there might be a period in which example1 still thinks it
is providing a final delivery service rather than a relay one
and LittleCo would be smart to plan for that.  Otherwise, so
far, so good. But eventually the contract between LittleCo and
example1 about mail service runs out and the the DNS is changed
to 

   LittleCo.example.     IN CNAME example1.net.
   www.LittleCo.example. IN CNAME example1.net.
   LittleCo.example.     MX 0 example3.net.

Now, for the case of concern, if someone has a cache that should
have expired but has not and opens an SMTP connection to
example1.net (which is also providing mail support for other
domains, so it cannot return a 5yz code at initial connection
time).  The client sends EHLO and MAIL commands as usual, then 
   RCPT TO:<someuser@littleco.example>

Question 1: Would we prefer that example1.com reply with 556 or
521, indicating that example1 is not providing mail service for
that domain, or 550 (no mailbox for that address).   Either of
the first two provide much more information than the 550 and, I
think, do not give out any secret information.

Question 2: Assuming 556 or 521, do we have a preference and
why?  Do we want to reserve 556 for connection-opening only so
521 is returned here?  If not, what is 521 good for?

Question 3: Sections 4.2.3 and 4.2.2 say, for 554, 
	"(Or, historically in the case of a connection-opening
	response, "No SMTP service here".  521 is now preferred
	for that function at connection-opening if the server
	never accepts mail.)"
Is that just wrong, i.e. should it say 556 instead of 521?

... and, now...

Suppose LittleCo is in the process of going out of business but
still owns the domain name.  Assuming it can do so, it changes
the DNS entries to

   LittleCo.example.     IN CNAME tombstone.example1.net.
   www.LittleCo.example. IN CNAME tombstone.example1.net.
   LittleCo.example.     MX 0 .

Now, if during some transition period (inside or outside the DNS
TTL), example3.net. gets a connection attempt exactly like the
one for example1.net above, i.e., the connection attempt
succeeds because example3.net provides SMTP service to domains
that have nothing to do with LittleCo, the EHLO and MAIL
commands go through without problems, and it then gets the same
RCPT command as above.  

Questions 4 and 5 are identical to Questions 1 and 2 above, but
it is not clear that the answers should be.

If it is clear what the WG wants the text to say in those five
cases, I can fix at least those parts of 4.2.4.2.   I am now
confused about the answers to some of those questions (although
I have preferences) and am wondering a bit why we introduced the
556 code (which might be close to Sabahattin's original
concern... or not).

    john








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From: "John R Levine" <johnl@taugh.com>
To: "John C Klensin" <john-ietf@jck.com>, emailcore@ietf.org
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Subject: Re: [Emailcore] 5321bis-10, code 556, 521, and maybe 554 (was: Re: 5321bis-09: Thinking About Interaction of Code 556 with 'postmaster')
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On Tue, 8 Mar 2022, John C Klensin wrote:
> time).  The client sends EHLO and MAIL commands as usual, then
>   RCPT TO:<someuser@littleco.example>
>
> Question 1: Would we prefer that example1.com reply with 556 or
> 521, indicating that example1 is not providing mail service for
> that domain, or 550 (no mailbox for that address).

In practice it's this or something close to it:

  550 5.1.0 Mail system is not configured to accept that recipient

> Question 3: Sections 4.2.3 and 4.2.2 say, for 554,
> 	"(Or, historically in the case of a connection-opening
> 	response, "No SMTP service here".  521 is now preferred
> 	for that function at connection-opening if the server
> 	never accepts mail.)"
> Is that just wrong, i.e. should it say 556 instead of 521?

No, that's fine.

> Now, if during some transition period (inside or outside the DNS
> TTL), example3.net. gets a connection attempt exactly like the
> one for example1.net above, i.e., the connection attempt
> succeeds because example3.net provides SMTP service to domains
> that have nothing to do with LittleCo, the EHLO and MAIL
> commands go through without problems, and it then gets the same
> RCPT command as above.
>
> Questions 4 and 5 are identical to Questions 1 and 2 above, but
> it is not clear that the answers should be.

Same answer:

  550 5.1.0 Mail system is not configured to accept that recipient

I don't know how many ways to say that MTAs know who they accept mail for 
and who they don't, but they don't know *why* they don't accept mail for 
the ones they don't.

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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Date: Tue, 22 Mar 2022 08:52:10 -0400
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Subject: [Emailcore] Relaxing the IANA registration requirement for SMTP Extensions in rfc5321bis
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Hi.

Having become increasingly convinced over the years that high
barriers to IANA registrations (of most types) don't necessarily
improve quality but definitely discourage registrations and that
the primary value of registrations is to prevent the same
keyword accidentally being used for different things, I'm in
favor of relaxing the requirements somewhat from Standards Track
or IESG-approved Experimental.

However, I'm afraid of losing something else in the process.
One of the key points in the early work on SMTP extensions was
the observation (I think first due to Marshall Rose), that too
many of them is a bad thing and that each new one poses
interoperability challenges.   That principle appears in 5321bis
in  the last two paragraphs of Section 2.2.1. 

The requirement for IETF consensus (or, with current IESG
procedures, at least a Last Call and opportunity for serious
discussion) provided, in addition to the presumed gatekeeping,
an opportunity for an IETF discussion and decision about whether
the extension is worth the trouble.  Dropping the registration
threshold even as far as Specification Required eliminates the
opportunity for that community discussion which has proven
helpful to authors of other registrations. We should mitigate
that loss by at least requiring the would-be registrants to
explain themselves.  That should not be a barrier to any serious
extension proposal but might, almost as a side effect, raise the
bar for silly vanity registrations.  The latter would presumably
be A Good Thing if it did not cause other problems.
 
Suggestion: RFC 5321 Section 8, IANA Considerations, describes
the three registries but does not actually specify what goes in
them, nor does it follow what is now the normal practice of
providing a specific registration template or list of fields and
descriptions of possible values [1].  For the SMTP Extensions
Registry, we should consider either specifying a template or a
list of things required in an application for a Service
Extension.  We could then require that the  registration
application (or other documentation) explain the problem that
the new extension is solving and the reasons why its benefits
outweigh the possible costs.

The idea above is compatible with either of the options in the
meeting slides (at least the last time I looked at them).

    --john


[1] Should the IESG decide to impose current standards, it is
fairly clear to me that Section 8 of RFC 5321 is not in
compliance with Section 2 of RFC 8126/ BCP 26.  So, unless
people are convinced that it will slip through because of the
older document(s), we may want to think about revising that
section anyway.


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Date: Tue, 22 Mar 2022 09:22:35 -0400
From: John C Klensin <john-ietf@jck.com>
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Subject: [Emailcore] RCPT commands, BCCs, and the "for" clause
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Hi.

I have been thinking about these (very connected, IMO) issues,
partially in conjunction with some side conversations.   My
first conclusion is that they really are one basic issue and
that trying to discuss them separately is just confusing us and
that previous versions of that confusion may have created a hole
in which we are continuing to dig.

The second conclusion is that RFC 5321 says rather more about
these topics than it should and that we are trying to fix the
issues that text causes by adding more text and risking even
more confusion (in other words, trying to get out of the hole by
digging deeper). With the understanding that none of the ideas
below are new except for the organization and context, my
current hunch is that 5321bis should:

(i) Remind people that a conforming SMTP server or
(non-submission) client doesn't look at header fields, much less
start performing heuristics on them, and hence does not have a
clue as to which RCPT commands (or their arguments) are
associated with "To:", "Cc:", or "Bcc:" header fields.  Section
7.8 provides a loophole for, e.g., malware resistance measures,
but does not change the principle.

(ii) Mention that no attempt should be made to include "for" in
a "Received:" header field if there is more than one RCPT
command present, noting that this is forbidden by the syntax
anyway.

(iii) Clarify the text that mentions that "for" can cause
unintended privacy disclosures and say that, if one is not sure
of the appropriateness of the clause and the information that
should go into it, it is generally better to just omit the
clause.

(iv) Mention as well that _any_ trace field might, under the
wrong set of circumstances, disclose information that someone
might consider sensitive and that, while those fields are often
essential for debugging messages that have run into transport
problems and may even be helpful in distinguishing spoofed or
otherwise problematic messages from more desirable traffic (and
even identifying the source of such bad traffic), complete
protection of anything that might be considered private would
argue for eliminating trace information entirely.

Wordsmithing and some decisions about where to use 2119/8174
language obviously needed, but I'm hoping we can agree on the
above or something like it as general principles.

We then get rid of all of the hair-splitting about internal
names and addresses on LANs, which addresses should be included
in "for" clauses and which ones avoided, etc.  If someone
believes they can persuade the WG that it is worth doing the
case analysis and offering more specific advice in the A/S they
should certainly try (and be ready to write text).  But, as far
as 5321bis is concerned, my recommendation is that we
concentrate on the above four points and tear everything else
out.  That would, IMO, improve clarity and and shorten 5321bis
by a few pages.

   --john


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From: Alexey Melnikov <aamelnikov@fastmail.fm>
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Date: Tue, 22 Mar 2022 15:08:50 +0100
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To: John C Klensin <john-ietf@jck.com>
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Subject: Re: [Emailcore] RCPT commands, BCCs, and the "for" clause
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Hi John,
(Replying as a WG participant)

> On 22 Mar 2022, at 14:22, John C Klensin <john-ietf@jck.com> wrote:
>=20
> =EF=BB=BFHi.
>=20
> I have been thinking about these (very connected, IMO) issues,
> partially in conjunction with some side conversations.   My
> first conclusion is that they really are one basic issue and
> that trying to discuss them separately is just confusing us and
> that previous versions of that confusion may have created a hole
> in which we are continuing to dig.
>=20
> The second conclusion is that RFC 5321 says rather more about
> these topics than it should and that we are trying to fix the
> issues that text causes by adding more text and risking even
> more confusion (in other words, trying to get out of the hole by
> digging deeper). With the understanding that none of the ideas
> below are new except for the organization and context, my
> current hunch is that 5321bis should:
>=20
> (i) Remind people that a conforming SMTP server or
> (non-submission) client doesn't look at header fields, much less
> start performing heuristics on them, and hence does not have a
> clue as to which RCPT commands (or their arguments) are
> associated with "To:", "Cc:", or "Bcc:" header fields.  Section
> 7.8 provides a loophole for, e.g., malware resistance measures,
> but does not change the principle.
>=20
> (ii) Mention that no attempt should be made to include "for" in
> a "Received:" header field if there is more than one RCPT
> command present, noting that this is forbidden by the syntax
> anyway.

I think this statement is stronger than currently specified in the draft and=
 is not something I agree. If a message has 2 RCPT TO recipients A and B (le=
t=E2=80=99s assume for simplicity that A and B are end user email addresses,=
 not mailing lists), I think it is perfectly ok to do either:

1) The same message with Received with no FOR is delivered to both A and B

 or

2) Recipient A receives a copy of the message with Received with FOR A, whil=
e recipient B receives a copy of the message with Received with FOR B.

Your statement (ii) prevents choice 2)
>=20
> (iii) Clarify the text that mentions that "for" can cause
> unintended privacy disclosures and say that, if one is not sure
> of the appropriateness of the clause and the information that
> should go into it, it is generally better to just omit the
> clause.
Agreed.
>=20
> (iv) Mention as well that _any_ trace field might, under the
> wrong set of circumstances, disclose information that someone
> might consider sensitive and that, while those fields are often
> essential for debugging messages that have run into transport
> problems and may even be helpful in distinguishing spoofed or
> otherwise problematic messages from more desirable traffic (and
> even identifying the source of such bad traffic), complete
> protection of anything that might be considered private would
> argue for eliminating trace information entirely.

Agreed.

> Wordsmithing and some decisions about where to use 2119/8174
> language obviously needed, but I'm hoping we can agree on the
> above or something like it as general principles.
>=20
> We then get rid of all of the hair-splitting about internal
> names and addresses on LANs, which addresses should be included
> in "for" clauses and which ones avoided, etc.  If someone
> believes they can persuade the WG that it is worth doing the
> case analysis and offering more specific advice in the A/S they
> should certainly try (and be ready to write text).  But, as far
> as 5321bis is concerned, my recommendation is that we
> concentrate on the above four points and tear everything else
> out.  That would, IMO, improve clarity and and shorten 5321bis
> by a few pages.

I am personally Ok with this direction, but I think I would like to see the n=
ew proposed text before fully committing to it. Is it something you can post=
 to the mailing list before Friday or at least soon-ish?

Thank you,
Alexey
>=20
>   --john
>=20
> --=20
> Emailcore mailing list
> Emailcore@ietf.org
> https://www.ietf.org/mailman/listinfo/emailcore


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Subject: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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Greetings.

I've reviewed the comments generated by my posting rev 3 here at the end of
January, and I've incorporated some of them.

The one that I didn't incorporate was one that Dave Crocker made to perhaps
discuss the concepts of Channel Security versus Object Security in section
5.5, Message-Level Confidentiality. While I thought the suggestion had
merit on its face, the fact that the section is just a paragraph talking
about how OpenPGP and S/MIME (and similar technologies) are out of scope
for the A/S made me decide not to add more text to this section.

Current revision follows, there's a place in the agenda to discuss it
during Friday's meeting.

=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

A/S Proposed Text - Confidentiality and Authentication

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 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

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 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 the
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.

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. Its name might suggest that it would be within scope for
this section of the Applicability Statement, but in fact it=E2=80=99s not.

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


--=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.

--000000000000980fbf05dacf72cb
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 reviewed the comments g=
enerated by my posting rev 3 here at the end of January, and I&#39;ve incor=
porated some of them.</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">The one that I didn&#39;t incorporate was one that=
 Dave Crocker made to perhaps discuss the concepts of Channel Security vers=
us Object Security in section 5.5, Message-Level Confidentiality. While I t=
hought the suggestion had merit on its face, the fact that the section is j=
ust a paragraph talking about how OpenPGP and S/MIME (and similar technolog=
ies) are out of scope for the A/S made me decide not to add more text to th=
is section.</div><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
ans-serif"><br></div><div class=3D"gmail_default" style=3D"font-family:taho=
ma,sans-serif">Current revision follows, there&#39;s a place in the agenda =
to discuss it during Friday&#39;s=C2=A0meeting.</div><div class=3D"gmail_de=
fault" style=3D"font-family:tahoma,sans-serif"><br></div><div class=3D"gmai=
l_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 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</div><di=
v><span id=3D"gmail-docs-internal-guid-527fab97-7fff-72bf-df46-e669956a6e75=
"><p dir=3D"ltr" style=3D"line-height:1.38;text-align:center;margin-top:0pt=
;margin-bottom:3pt"><span style=3D"font-size:26pt;font-family:Arial;color:r=
gb(0,0,0);background-color:transparent;font-variant-numeric:normal;font-var=
iant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">A/S Pr=
oposed Text - Confidentiality and Authentication</span></p><br><p dir=3D"lt=
r" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span styl=
e=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-weight:700;f=
ont-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:ba=
seline;white-space:pre-wrap">5. Confidentiality and Authentication with SMT=
P</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin=
-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,=
89,89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-=
align:baseline;white-space:pre-wrap">SMTP is specified without embedded mec=
hanisms for authentication or confidentiality; its traffic is therefore =E2=
=80=9Cin the clear=E2=80=9D. Years of operational experience have shown tha=
t such transmission exposes the message to easy compromise, including wiret=
apping 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 Secu=
rity (TLS - RFC8446) to provide both confidentiality and authentication in =
the transmission of messages. This section discusses those topics and their=
 most common uses.</span></p><p dir=3D"ltr" style=3D"line-height:1.656;marg=
in-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:Ar=
ial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian=
:normal;vertical-align:baseline;white-space:pre-wrap">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 d=
irectly from RFC8446.</span></p><ul style=3D"margin-top:0px;margin-bottom:0=
px"><li dir=3D"ltr" style=3D"list-style-type:disc;font-size:11pt;font-famil=
y:Arial;color:rgb(89,89,89);background-color:transparent;font-variant-numer=
ic:normal;font-variant-east-asian:normal;vertical-align:baseline;white-spac=
e:pre"><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bott=
om:0pt" role=3D"presentation"><span style=3D"font-size:11pt;font-variant-nu=
meric:normal;font-variant-east-asian:normal;vertical-align:baseline;white-s=
pace:pre-wrap">Authentication is the process of establishing the identity o=
f one or more of the endpoints of a communication channel. TLS only require=
s authentication of the server side of the communication channel; authentic=
ation of the client side is optional.</span></p></li><li dir=3D"ltr" style=
=3D"list-style-type:disc;font-size:11pt;font-family:Arial;color:rgb(89,89,8=
9);background-color:transparent;font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre"><p dir=3D"ltr" sty=
le=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt" role=3D"presenta=
tion"><span style=3D"font-size:11pt;font-variant-numeric:normal;font-varian=
t-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">The term =
=E2=80=9Cconfidentiality=E2=80=9D describes a state where the data (i.e., t=
he message) is transmitted in a way that it is only visible to the endpoint=
s of a communication channel.</span></p></li></ul><p dir=3D"ltr" style=3D"l=
ine-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-siz=
e:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;fo=
nt-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">=
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 cor=
rect. Rather, encryption using TLS is the current method by which confident=
iality is achieved with SMTP, but that does not mean that future methods mi=
ght not be developed.</span></p><p dir=3D"ltr" style=3D"line-height:1.656;m=
argin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family=
:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-as=
ian:normal;vertical-align:baseline;white-space:pre-wrap">Note: With typical=
 email use of TLS, authentication only is performed by the sending client o=
f the target receiving server. That is, it serves to validate that the conn=
ection has been made to the intended server, but does not validate who init=
iated it.</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0p=
t;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color=
:rgb(89,89,89);font-weight:700;font-variant-numeric:normal;font-variant-eas=
t-asian:normal;vertical-align:baseline;white-space:pre-wrap">5.1 Optional C=
onfidentiality</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-t=
op:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;=
color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian:nor=
mal;vertical-align:baseline;white-space:pre-wrap">The most common implement=
ation of message confidentiality is what=E2=80=99s known as =E2=80=9Copport=
unistic TLS=E2=80=9D, which is frequently referred to as =E2=80=9Copportuni=
stic encryption=E2=80=9D. With this method, a receiving server announces in=
 its greeting that it is capable of supporting TLS encryption through the p=
resence of the =E2=80=9CSTARTTLS=E2=80=9D 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.</span></p><p dir=3D"ltr" style=3D"li=
ne-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size=
:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;fon=
t-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">O=
pportunistic TLS is confidentiality without authentication, because no effo=
rt is made to authenticate the receiving server, and it is optional confide=
ntiality due to the ability to fall back to transmission in the clear if a =
secure connection cannot be established. That said, most modern implementat=
ions of SMTP support this method, especially at the largest mailbox provide=
rs, and so the vast majority of email traffic is encrypted during its time =
transiting from the client to the server.=C2=A0</span></p><p dir=3D"ltr" st=
yle=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"=
font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:n=
ormal;font-variant-east-asian:normal;vertical-align:baseline;white-space:pr=
e-wrap">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 withi=
n the MTAs relaying the message or at its destination. In fact, storage in =
plain text should be expected!</span></p><p dir=3D"ltr" style=3D"line-heigh=
t:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;fo=
nt-family:Arial;color:rgb(89,89,89);font-weight:700;font-variant-numeric:no=
rmal;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre=
-wrap">5.2 Required Confidentiality, with Receiving Server Authentication</=
span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bo=
ttom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,=
89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-ali=
gn:baseline;white-space:pre-wrap">Two protocols exist that move message con=
fidentiality from optional to required (with conditions as noted below) - M=
TA-STS [RFC8461] and DANE for SMTP [RFC7672]. While they differ in their im=
plementation details, receiving servers relying on either protocol are stat=
ing that they only accept mail if the transmission can be encrypted with TL=
S, and a failure to negotiate a secure connection MUST result in the sendin=
g client refusing to transmit the message.=C2=A0</span></p><p dir=3D"ltr" s=
tyle=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D=
"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:=
normal;font-variant-east-asian:normal;vertical-align:baseline;white-space:p=
re-wrap">These two protocols differ from Opportunistic TLS in that they req=
uire receiving server authentication and there is no fallback to sending in=
 the clear if negotiation of an encrypted connection fails.</span></p><p di=
r=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><sp=
an style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-varia=
nt-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;wh=
ite-space:pre-wrap">Note: Both protocols mentioned in this section rely not=
 only on the receiving server but also the sending client supporting the pr=
otocol intended to be used. If the sending client does not implement or und=
erstand the protocol requested by the receiving server, the sending client =
will use Opportunistic TLS or clear-text to transmit the message.</span></p=
><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12p=
t"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font=
-weight:700;font-variant-numeric:normal;font-variant-east-asian:normal;vert=
ical-align:baseline;white-space:pre-wrap">5.3 Message-Level Authentication<=
/span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-b=
ottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89=
,89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-al=
ign:baseline;white-space:pre-wrap">Protocols exist to allow for authenticat=
ion 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 a=
uthentication checks performed at that hop.</span></p><p dir=3D"ltr" style=
=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"fon=
t-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:norm=
al;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre-w=
rap">All of these are outside the scope of this document, as they are outsi=
de 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 identit=
y of the receiving server.</span></p><p dir=3D"ltr" style=3D"line-height:1.=
656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-f=
amily:Arial;color:rgb(89,89,89);font-weight:700;font-variant-numeric:normal=
;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wra=
p">5.4 SMTP Authentication</span></p><p dir=3D"ltr" style=3D"line-height:1.=
656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-f=
amily:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre-wrap">SMTP Authenti=
cation, which is often abbreviated as SMTP AUTH, is an extension to SMTP. I=
ts name might suggest that it would be within scope for this section of the=
 Applicability Statement, but in fact it=E2=80=99s not.</span></p><p dir=3D=
"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span s=
tyle=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-n=
umeric:normal;font-variant-east-asian:normal;vertical-align:baseline;white-=
space:pre-wrap">SMTP AUTH defines a method for a client to identify itself =
to a Message Submission Agent (MSA) when presenting a message for transmiss=
ion, usually using port 587 rather than the traditional port 25. The most c=
ommon 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 con=
figuring their MUA for sending mail.</span></p><p dir=3D"ltr" style=3D"line=
-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:1=
1pt;font-family:Arial;color:rgb(89,89,89);font-weight:700;font-variant-nume=
ric:normal;font-variant-east-asian:normal;vertical-align:baseline;white-spa=
ce:pre-wrap">5.5 Message-Level Confidentiality</span></p><p dir=3D"ltr" sty=
le=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"f=
ont-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:no=
rmal;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre=
-wrap">Protocols such as S/MIME (RFC8551) and OpenPGP (RFC4880) exist to al=
low for message confidentiality outside of the operation of SMTP. That is t=
o say, using these protocols results in encryption of the message prior to =
its being submitted to the SMTP communications channel, and decryption of t=
he message is the responsibility of the message recipient. There are numero=
us implementations of these protocols, too many to list here. As they opera=
te fully independent of SMTP, they are out of scope for this document.</spa=
n></p><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 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</div><div><span id=3D"gmail-docs-internal-guid-527fab97-7ff=
f-72bf-df46-e669956a6e75"><br class=3D"gmail-Apple-interchange-newline"></s=
pan></div><br></span></div>-- <br><div dir=3D"ltr" class=3D"gmail_signature=
" data-smartmail=3D"gmail_signature"><span><p dir=3D"ltr" style=3D"line-hei=
ght:1.656;margin-top:0pt;margin-bottom:0pt"></p><div style=3D"text-align:le=
ft"><span style=3D"vertical-align:baseline;white-space:pre-wrap;font-size:s=
mall;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, S=
tandards and Ecosystem</span></div><span style=3D"vertical-align:baseline;w=
hite-space:pre-wrap;font-size:small;font-family:Arial"><div style=3D"text-a=
lign:left"><span style=3D"vertical-align:baseline"><b>e:</b></span><span st=
yle=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> 703.220.4153</span><span></span></div><div st=
yle=3D"text-align:left"><img style=3D"width:175px;height:43px" src=3D"https=
://hosted-packages.s3-us-west-1.amazonaws.com/Valimail+Logo.png"></div></sp=
an><p dir=3D"ltr" style=3D"background-color:rgb(255,255,255);line-height:1.=
38;margin-top:0pt;margin-bottom:0pt"><font face=3D"Arial" color=3D"#666666"=
><span style=3D"font-size:10.6667px;white-space:pre-wrap">This email and al=
l data transmitted with it contains confidential and/or proprietary informa=
tion intended solely for the use of individual(s) authorized to receive it.=
 If you are not an intended and authorized recipient you are hereby notifie=
d of any use, disclosure, copying or distribution of the information includ=
ed in this transmission is prohibited and may be unlawful. Please immediate=
ly notify the sender by replying to this email and then delete it from your=
 system.</span></font></p></span></div></div>

--000000000000980fbf05dacf72cb--


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From: "John Levine" <johnl@taugh.com>
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Subject: Re: [Emailcore] Relaxing the IANA registration requirement for SMTP Extensions in rfc5321bis
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It appears that John C Klensin  <john-ietf@jck.com> said:
>keyword accidentally being used for different things, I'm in
>favor of relaxing the requirements somewhat from Standards Track
>or IESG-approved Experimental.

My inclination is somewhere between specification required and
expert review, with the understanding that the point of the review
is just to see that the specification is at least superficially
plausible.  We have our share of unused extensions (MTRK, CONNEG, ...)
and I'm not worried that there is a flood of worse ones waiting.

>Suggestion: RFC 5321 Section 8, IANA Considerations, describes
>the three registries but does not actually specify what goes in
>them, nor does it follow what is now the normal practice of
>providing a specific registration template or list of fields and
>descriptions of possible values [1].  For the SMTP Extensions
>Registry, we should consider either specifying a template or a
>list of things required in an application for a Service
>Extension.

That would be a good idea.  Yesterday Alexey and I realized that
5321 says VRFY is a service extension that somehow never made it
into the registry.

R's,
John


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From: Alexey Melnikov <aamelnikov@fastmail.fm>
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Date: Tue, 22 Mar 2022 18:27:57 +0100
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To: Todd Herr <todd.herr=40valimail.com@dmarc.ietf.org>
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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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Hi Todd,
(With my WG participant hat on)

> On 22 Mar 2022, at 15:31, Todd Herr <todd.herr=3D40valimail.com@dmarc.ietf=
.org> wrote:
>=20
> =EF=BB=BF
> Greetings.
>=20
> I've reviewed the comments generated by my posting rev 3 here at the end o=
f January, and I've incorporated some of them.
>=20
> The one that I didn't incorporate was one that Dave Crocker made to perhap=
s discuss the concepts of Channel Security versus Object Security in section=
 5.5, Message-Level Confidentiality. While I thought the suggestion had meri=
t on its face, the fact that the section is just a paragraph talking about h=
ow OpenPGP and S/MIME (and similar technologies) are out of scope for the A/=
S made me decide not to add more text to this section.
>=20
> Current revision follows, there's a place in the agenda to discuss it duri=
ng Friday's meeting.
>=20
> =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

Thank you for this text. Minor comments below:

> A/S Proposed Text - Confidentiality and Authentication
>=20
> 5. Confidentiality and Authentication with SMTP
>=20
> SMTP is specified without embedded mechanisms for authentication or confid=
entiality; its traffic is therefore =E2=80=9Cin the clear=E2=80=9D. Years of=
 operational experience have shown that such transmission exposes the messag=
e to easy compromise, including wiretapping and spoofing. To mitigate these r=
isks, operation of SMTP has evolved over the years so that it is used with t=
he benefit of Transport Layer Security (TLS - RFC8446) to provide both confi=
dentiality and authentication in the transmission of messages. This section d=
iscusses those topics and their most common uses.
>=20
> 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 th=
at we will borrow directly from RFC8446.
>=20
> Authentication is the process of establishing the identity of one or more o=
f the endpoints of a communication channel. TLS only requires authentication=
 of the server side of the communication channel; authentication of the clie=
nt side is optional.
> The term =E2=80=9Cconfidentiality=E2=80=9D describes a state where the dat=
a (i.e., the message) is transmitted in a way that it is only visible to the=
 endpoints of a communication channel.
>=20
> 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 corr=
ect. Rather, encryption using TLS is the current method by which confidentia=
lity is achieved with SMTP, but that does not mean that future methods might=
 not be developed.
>=20
> Note: With typical email use of TLS, authentication only is performed by t=
he sending client of the target receiving server. That is, it serves to vali=
date that the connection has been made to the intended server, but does not v=
alidate who initiated it.
>=20
> 5.1 Optional Confidentiality
>=20
> The most common implementation of message confidentiality is what=E2=80=99=
s 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 recei=
ving server announces in its greeting that it is capable of supporting TLS e=
ncryption through the presence of the =E2=80=9CSTARTTLS=E2=80=9D keyword. Th=
e sending client then attempts to negotiate an encrypted connection, and if s=
uccessful, transmits the message in encrypted form; if negotiation fails, th=
e client falls back to sending the message in clear text.
>=20
> Opportunistic TLS is confidentiality without authentication, because no ef=
fort is made to authenticate the receiving server, and it is optional confid=
entiality due to the ability to fall back to transmission in the clear if a s=
ecure connection cannot be established. That said, most modern implementatio=
ns of SMTP support this method, especially at the largest mailbox providers,=
 and so the vast majority of email traffic is encrypted during its time tran=
siting from the client to the server.=20
>=20
> Note: While TLS provides protection while the message is in transit for a s=
ingle SMTP connection, a message that is encrypted for one SMTP hop might no=
t be encrypted on the next hop and it might not be encrypted within the MTAs=
 relaying the message or at its destination. In fact, storage in plain text s=
hould be expected!
>=20
I think you should move the above note to Section 5, as it applies equally t=
o opportunistic and mandated confidentiality.

> 5.2 Required Confidentiality, with Receiving Server Authentication
>=20
> Two protocols exist that move message confidentiality from optional to req=
uired (with conditions as noted below) - MTA-STS [RFC8461] and DANE for SMTP=
 [RFC7672]. While they differ in their implementation details, receiving ser=
vers relying on either protocol are stating that they only accept mail if th=
e transmission can be encrypted with TLS, and a failure to negotiate a secur=
e connection MUST result in the sending client refusing to transmit the mess=
age.=20
>=20
> These two protocols differ from Opportunistic TLS in that they require rec=
eiving server authentication and there is no fallback to sending in the clea=
r if negotiation of an encrypted connection fails.
>=20
> Note: Both protocols mentioned in this section rely not only on the receiv=
ing server but also the sending client supporting the protocol intended to b=
e used. If the sending client does not implement or understand the protocol r=
equested by the receiving server, the sending client will use Opportunistic T=
LS or clear-text to transmit the message.
>=20
> 5.3 Message-Level Authentication
>=20
> Protocols exist to allow for authentication of different identities associ=
ated with an email message - SPF [RFC7208] and DKIM [RFC6376]. A third proto=
col, DMARC [RFC7489], relies on SPF and DKIM to allow for validation of the d=
omain in the visible =46rom header, and a fourth, ARC [RFC8617], provides a w=
ay for each hop to record results of authentication checks performed at that=
 hop.
>=20
> All of these are outside the scope of this document, as they are outside t=
he scope of SMTP. They deal with validating the authorized usage of one or m=
ore domains in an email message, and not with establishing the identity of t=
he receiving server.
>=20
> 5.4 SMTP Authentication
>=20
> SMTP Authentication, which is often abbreviated as SMTP AUTH, is an extens=
ion to SMTP. Its name might suggest that it would be within scope for this s=
ection of the Applicability Statement, but in fact it=E2=80=99s not.
>=20
> SMTP AUTH defines a method for a client to identify itself to a Message Su=
bmission Agent (MSA)=20
>=20
While this is the most common use, SMTP AUTH is actually not limited to MSAs=
.

I would reword the above to say that why SMTP AUTH is defined for both MSAs a=
nd MTAs, it is most commonly used with MSAs, and thus it is out of scope for=
 A/S.

> when presenting a message for transmission, usually using port 587 rather t=
han the traditional port 25.=20
>=20
You need a reference here.
> The most common implementation of SMTP AUTH is for a person to present a u=
sername and password to their mailbox provider=E2=80=99s outbound SMTP serve=
r when configuring their MUA for sending mail.
>=20
> 5.5 Message-Level Confidentiality
>=20
> Protocols such as S/MIME (RFC8551) and OpenPGP (RFC4880) exist to allow fo=
r message confidentiality=20
>=20
=E2=80=9Cand integrity=E2=80=9D
> outside of the operation of SMTP. That is to say, using these protocols re=
sults in encryption of the message prior to its being submitted to the SMTP c=
ommunications channel, and decryption of the message is the responsibility o=
f the message recipient. There are numerous implementations of these protoco=
ls, too many to list here. As they operate fully independent of SMTP, they a=
re out of scope for this document.
>=20
> =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
>=20
>=20
> --=20
> Todd Herr  | Technical Director, Standards and Ecosystem
> e: todd.herr@valimail.com=20
> m: 703.220.4153
>=20
> This email and all data transmitted with it contains confidential and/or p=
roprietary information intended solely for the use of individual(s) authoriz=
ed to receive it. If you are not an intended and authorized recipient you ar=
e hereby notified of any use, disclosure, copying or distribution of the inf=
ormation included in this transmission is prohibited and may be unlawful. Pl=
ease immediately notify the sender by replying to this email and then delete=
 it from your system.
> --=20
> Emailcore mailing list
> Emailcore@ietf.org
> https://www.ietf.org/mailman/listinfo/emailcore

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<html><head><meta http-equiv=3D"content-type" content=3D"text/html; charset=3D=
utf-8"></head><body dir=3D"auto"><div dir=3D"ltr">Hi Todd,</div><div dir=3D"=
ltr">(With my WG participant hat on)</div><div dir=3D"ltr"><br></div><div di=
r=3D"ltr"><blockquote type=3D"cite">On 22 Mar 2022, at 15:31, Todd Herr &lt;=
todd.herr=3D40valimail.com@dmarc.ietf.org&gt; wrote:<br><br></blockquote></d=
iv><blockquote type=3D"cite"><div dir=3D"ltr">=EF=BB=BF<div dir=3D"ltr"><div=
 class=3D"gmail_default" style=3D"font-family:tahoma,sans-serif">Greetings.<=
br clear=3D"all"></div><div class=3D"gmail_default" style=3D"font-family:tah=
oma,sans-serif"><br></div><div class=3D"gmail_default" style=3D"font-family:=
tahoma,sans-serif">I've reviewed the comments generated by my posting rev 3 h=
ere at the end of January, and I've incorporated some of them.</div><div cla=
ss=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 one that I=
 didn't incorporate was one that Dave Crocker made to perhaps discuss the co=
ncepts of Channel Security versus Object Security in section 5.5, Message-Le=
vel Confidentiality. While I thought the suggestion had merit on its face, t=
he fact that the section is just a paragraph talking about how OpenPGP and S=
/MIME (and similar technologies) are out of scope for the A/S made me decide=
 not to add more text to this section.</div><div class=3D"gmail_default" sty=
le=3D"font-family:tahoma,sans-serif"><br></div><div class=3D"gmail_default" s=
tyle=3D"font-family:tahoma,sans-serif">Current revision follows, there's a p=
lace in the agenda to discuss it during Friday's&nbsp;meeting.</div><div cla=
ss=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">=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</div><=
/div></div></blockquote><div><br></div>Thank you for this text. Minor commen=
ts below:<div><br><blockquote type=3D"cite"><div dir=3D"ltr"><div dir=3D"ltr=
"><div><span id=3D"gmail-docs-internal-guid-527fab97-7fff-72bf-df46-e669956a=
6e75"><p dir=3D"ltr" style=3D"line-height:1.38;text-align:center;margin-top:=
0pt;margin-bottom:3pt"><span style=3D"font-size:26pt;font-family:Arial;color=
:rgb(0,0,0);background-color:transparent;font-variant-numeric:normal;font-va=
riant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">A/S Pr=
oposed Text - Confidentiality and Authentication</span></p><br><p dir=3D"ltr=
" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D=
"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-weight:700;font-v=
ariant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline=
;white-space:pre-wrap">5. Confidentiality and Authentication with SMTP</span=
></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:=
12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);fo=
nt-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:base=
line;white-space:pre-wrap">SMTP is specified without embedded mechanisms for=
 authentication or confidentiality; its traffic is therefore =E2=80=9Cin the=
 clear=E2=80=9D. Years of operational experience have shown that such transm=
ission exposes the message to easy compromise, including wiretapping and spo=
ofing. 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 - RFC8=
446) to provide both confidentiality and authentication in the transmission o=
f messages. This section discusses those topics and their most common uses.<=
/span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bo=
ttom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,8=
9);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align=
:baseline;white-space:pre-wrap">It is important that the reader understand w=
hat is meant by the terms =E2=80=9CAuthentication=E2=80=9D and =E2=80=9CConf=
identiality=E2=80=9D, and for that we will borrow directly from RFC8446.</sp=
an></p><ul style=3D"margin-top:0px;margin-bottom:0px"><li dir=3D"ltr" style=3D=
"list-style-type:disc;font-size:11pt;font-family:Arial;color:rgb(89,89,89);b=
ackground-color:transparent;font-variant-numeric:normal;font-variant-east-as=
ian: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"><s=
pan style=3D"font-size:11pt;font-variant-numeric:normal;font-variant-east-as=
ian:normal;vertical-align:baseline;white-space:pre-wrap">Authentication is t=
he process of establishing the identity of one or more of the endpoints of a=
 communication channel. TLS only requires authentication of the server side o=
f the communication channel; authentication of the client side is optional.<=
/span></p></li><li dir=3D"ltr" style=3D"list-style-type:disc;font-size:11pt;=
font-family:Arial;color:rgb(89,89,89);background-color:transparent;font-vari=
ant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;wh=
ite-space:pre"><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;marg=
in-bottom:12pt" role=3D"presentation"><span style=3D"font-size:11pt;font-var=
iant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;w=
hite-space:pre-wrap">The term =E2=80=9Cconfidentiality=E2=80=9D describes a s=
tate where the data (i.e., the message) is transmitted in a way that it is o=
nly visible to the endpoints of a communication channel.</span></p></li></ul=
><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt=
"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-v=
ariant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline=
;white-space:pre-wrap">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 thi=
s is not quite correct. Rather, encryption using TLS is the current method b=
y which confidentiality is achieved with SMTP, but that does not mean that f=
uture methods might not be developed.</span></p><p dir=3D"ltr" style=3D"line=
-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11=
pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-va=
riant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">Note: W=
ith typical email use of TLS, authentication only is performed by the sendin=
g 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 w=
ho initiated it.</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-=
top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;=
color:rgb(89,89,89);font-weight:700;font-variant-numeric:normal;font-variant=
-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">5.1 Optiona=
l Confidentiality</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin=
-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial=
;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-asian:nor=
mal;vertical-align:baseline;white-space:pre-wrap">The most common implementa=
tion of message confidentiality is what=E2=80=99s known as =E2=80=9Copportun=
istic TLS=E2=80=9D, which is frequently referred to as =E2=80=9Copportunisti=
c encryption=E2=80=9D. With this method, a receiving server announces in its=
 greeting that it is capable of supporting TLS encryption through the presen=
ce of the =E2=80=9CSTARTTLS=E2=80=9D keyword. The sending client then attemp=
ts to negotiate an encrypted connection, and if successful, transmits the me=
ssage in encrypted form; if negotiation fails, the client falls back to send=
ing the message in clear text.</span></p><p dir=3D"ltr" style=3D"line-height=
:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font=
-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-e=
ast-asian:normal;vertical-align:baseline;white-space:pre-wrap">Opportunistic=
 TLS is confidentiality without authentication, because no effort is made to=
 authenticate the receiving server, and it is optional confidentiality due t=
o the ability to fall back to transmission in the clear if a secure connecti=
on cannot be established. That said, most modern implementations of SMTP sup=
port this method, especially at the largest mailbox providers, and so the va=
st majority of email traffic is encrypted during its time transiting from th=
e client to the server.&nbsp;</span></p><p dir=3D"ltr" style=3D"line-height:=
1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-=
family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre-wrap">Note: While TL=
S provides protection while the message is in transit for a single SMTP conn=
ection, a message that is encrypted for one SMTP hop might not be encrypted o=
n the next hop and it might not be encrypted within the MTAs relaying the me=
ssage or at its destination. In fact, storage in plain text should be expect=
ed!</span></p></span></div></div></div></blockquote><div>I think you should m=
ove the above note to Section 5, as it applies equally to opportunistic and m=
andated confidentiality.</div><div><br></div><blockquote type=3D"cite"><div d=
ir=3D"ltr"><div dir=3D"ltr"><div><span id=3D"gmail-docs-internal-guid-527fab=
97-7fff-72bf-df46-e669956a6e75"><p dir=3D"ltr" style=3D"line-height:1.656;ma=
rgin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-family:A=
rial;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">5.2 Re=
quired Confidentiality, with Receiving Server Authentication</span></p><p di=
r=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><spa=
n style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant=
-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;white=
-space:pre-wrap">Two protocols exist that move message confidentiality from o=
ptional 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 acc=
ept mail if the transmission can be encrypted with TLS, and a failure to neg=
otiate a secure connection MUST result in the sending client refusing to tra=
nsmit the message.&nbsp;</span></p><p dir=3D"ltr" style=3D"line-height:1.656=
;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-famil=
y:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east-as=
ian:normal;vertical-align:baseline;white-space:pre-wrap">These two protocols=
 differ from Opportunistic TLS in that they require receiving server authent=
ication and there is no fallback to sending in the clear if negotiation of a=
n encrypted connection fails.</span></p><p dir=3D"ltr" style=3D"line-height:=
1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-=
family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-ea=
st-asian:normal;vertical-align:baseline;white-space:pre-wrap">Note: Both pro=
tocols mentioned in this section rely not only on the receiving server but a=
lso the sending client supporting the protocol intended to be used. If the s=
ending client does not implement or understand the protocol requested by the=
 receiving server, the sending client will use Opportunistic TLS or clear-te=
xt to transmit the message.</span></p><p dir=3D"ltr" style=3D"line-height:1.=
656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-fa=
mily:Arial;color:rgb(89,89,89);font-weight:700;font-variant-numeric:normal;f=
ont-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">=
5.3 Message-Level Authentication</span></p><p dir=3D"ltr" style=3D"line-heig=
ht:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;fo=
nt-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant=
-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">Protocols e=
xist to allow for authentication of different identities associated with an e=
mail message - SPF [RFC7208] and DKIM [RFC6376]. A third protocol, DMARC [RFC=
7489], relies on SPF and DKIM to allow for validation of the domain in the v=
isible =46rom header, and a fourth, ARC [RFC8617], provides a way for each h=
op to record results of authentication checks performed at that hop.</span><=
/p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12=
pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font=
-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:baseli=
ne;white-space:pre-wrap">All of these are outside the scope of this document=
, as they are outside the scope of SMTP. They deal with validating the autho=
rized usage of one or more domains in an email message, and not with establi=
shing the identity of the receiving server.</span></p><p dir=3D"ltr" style=3D=
"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-si=
ze:11pt;font-family:Arial;color:rgb(89,89,89);font-weight:700;font-variant-n=
umeric:normal;font-variant-east-asian:normal;vertical-align:baseline;white-s=
pace:pre-wrap">5.4 SMTP Authentication</span></p><p dir=3D"ltr" style=3D"lin=
e-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:1=
1pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-v=
ariant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap">SMTP A=
uthentication, which is often abbreviated as SMTP AUTH, is an extension to S=
MTP. Its name might suggest that it would be within scope for this section o=
f the Applicability Statement, but in fact it=E2=80=99s not.</span></p><p di=
r=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><spa=
n style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant=
-numeric:normal;font-variant-east-asian:normal;vertical-align:baseline;white=
-space:pre-wrap">SMTP AUTH defines a method for a client to identify itself t=
o a Message Submission Agent (MSA) </span></p></span></div></div></div></blo=
ckquote>While this is the most common use, SMTP AUTH is actually not limited=
 to MSAs.<div><br></div><div>I would reword the above to say that why SMTP A=
UTH is defined for both MSAs and MTAs, it is most commonly used with MSAs, a=
nd thus it is out of scope for A/S.</div><div><br><blockquote type=3D"cite">=
<div dir=3D"ltr"><div dir=3D"ltr"><div><span id=3D"gmail-docs-internal-guid-=
527fab97-7fff-72bf-df46-e669956a6e75"><p dir=3D"ltr" style=3D"line-height:1.=
656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font-size:11pt;font-fa=
mily:Arial;color:rgb(89,89,89);font-variant-numeric:normal;font-variant-east=
-asian:normal;vertical-align:baseline;white-space:pre-wrap">when presenting a=
 message for transmission, usually using port 587 rather than the traditiona=
l port 25. </span></p></span></div></div></div></blockquote><div>You need a r=
eference here.</div><blockquote type=3D"cite"><div dir=3D"ltr"><div dir=3D"l=
tr"><div><span id=3D"gmail-docs-internal-guid-527fab97-7fff-72bf-df46-e66995=
6a6e75"><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bott=
om:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89)=
;font-variant-numeric:normal;font-variant-east-asian:normal;vertical-align:b=
aseline;white-space:pre-wrap">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 configuring their MUA for sending mail.</s=
pan></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margin-bott=
om:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,89,89)=
;font-weight:700;font-variant-numeric:normal;font-variant-east-asian:normal;=
vertical-align:baseline;white-space:pre-wrap">5.5 Message-Level Confidential=
ity</span></p><p dir=3D"ltr" style=3D"line-height:1.656;margin-top:0pt;margi=
n-bottom:12pt"><span style=3D"font-size:11pt;font-family:Arial;color:rgb(89,=
89,89);font-variant-numeric:normal;font-variant-east-asian:normal;vertical-a=
lign:baseline;white-space:pre-wrap">Protocols such as S/MIME (RFC8551) and O=
penPGP (RFC4880) exist to allow for message confidentiality </span></p></spa=
n></div></div></div></blockquote>=E2=80=9Cand integrity=E2=80=9D<br><blockqu=
ote type=3D"cite"><div dir=3D"ltr"><div dir=3D"ltr"><div><span id=3D"gmail-d=
ocs-internal-guid-527fab97-7fff-72bf-df46-e669956a6e75"><p dir=3D"ltr" style=
=3D"line-height:1.656;margin-top:0pt;margin-bottom:12pt"><span style=3D"font=
-size:11pt;font-family:Arial;color:rgb(89,89,89);font-variant-numeric:normal=
;font-variant-east-asian:normal;vertical-align:baseline;white-space:pre-wrap=
">outside of the operation of SMTP. That is to say, using these protocols re=
sults in encryption of the message prior to its being submitted to the SMTP c=
ommunications channel, and decryption of the message is the responsibility o=
f the message recipient. There are numerous implementations of these protoco=
ls, too many to list here. As they operate fully independent of SMTP, they a=
re out of scope for this document.</span></p><div class=3D"gmail_default" st=
yle=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 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</div><div><span id=3D"gmail=
-docs-internal-guid-527fab97-7fff-72bf-df46-e669956a6e75"><br class=3D"gmail=
-Apple-interchange-newline"></span></div><br></span></div>-- <br><div dir=3D=
"ltr" class=3D"gmail_signature" data-smartmail=3D"gmail_signature"><span><p d=
ir=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:pre-wrap">=
 | Technical Director, Standards and Ecosystem</span></div><span style=3D"ve=
rtical-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></di=
v></span><span><div><span><b>m:</b></span><span> 703.220.4153</span><span></=
span></div><div style=3D"text-align:left"><img style=3D"width:175px;height:4=
3px" src=3D"https://hosted-packages.s3-us-west-1.amazonaws.com/Valimail+Logo=
.png" data-unique-identifier=3D""></div></span><p dir=3D"ltr" style=3D"backg=
round-color:rgb(255,255,255);line-height:1.38;margin-top:0pt;margin-bottom:0=
pt"><font face=3D"Arial" color=3D"#666666"><span style=3D"font-size:10.6667p=
x;white-space:pre-wrap">This email and all data transmitted with it contains=
 confidential and/or proprietary information intended solely for the use of i=
ndividual(s) authorized to receive it. If you are not an intended and author=
ized recipient you are hereby notified of any use, disclosure, copying or di=
stribution of the information included in this transmission is prohibited an=
d may be unlawful. Please immediately notify the sender by replying to this e=
mail and then delete it from your system.</span></font></p></span></div></di=
v>
<span>-- </span><br><span>Emailcore mailing list</span><br><span>Emailcore@i=
etf.org</span><br><span>https://www.ietf.org/mailman/listinfo/emailcore</spa=
n><br></div></blockquote></div></div></body></html>=

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From: Dave Crocker <dhc@dcrocker.net>
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Subject: [Emailcore] Emailcore wg charter
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G'day,

Seeing an email citing Ticket #54, as well as a new posting for 
rfc5321bis, I wonder whether all of the work being done on the revisions 
is within the working group's charter?

The charter has language typical for revision efforts needing tight 
focus, seeking to limit changes and potential disruption for the 
installed base.  Specifically...

Emailcore Charter:

    https://datatracker.ietf.org/doc/charter-ietf-emailcore/

    This working group will conduct a limited review and revision to the base email specifications
    ...
    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.
    ...
    However, no new protocol extensions or amendments will be considered

54 ticket items seems like quite a few, given the constraints.  As for 
changes to the SMTP specification, consider the diff between RFC 5321 
and latest rfc5321bis draft:

    https://www.ietf.org/rfcdiff?url1=rfc5321&url2=draft-ietf-emailcore-rfc5321bis-10
    <https://www.ietf.org/rfcdiff?url1=rfc5321&url2=draft-ietf-emailcore-rfc5321bis-10>

A few questions to consider:

  * Are enough wg participants able and willing to justify every change,
    in detail, as conforming to the charter? Simply put, why were they
    essential, within the charter constraints?
  * Given the number of changes, what is the basis for believing that an
    average reader will be able to apply the revised specification,
    while ensuring continued interoperability, especially given how
    creative readers can be with new text?

The concern is not whether any given change is broadly reasonable or a 
generally good idea, but whether it is essential to the immediate 
working group goal and within its charter?

One could reasonably expect significant evidence of a problem that needs 
fixing, for each change.


d/

-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net

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<html>
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    <meta http-equiv="content-type" content="text/html; charset=UTF-8">
  </head>
  <body>
    <p>G'day,</p>
    <p>Seeing an email citing Ticket #54, as well as a new posting for
      rfc5321bis, I wonder whether all of the work being done on the
      revisions is within the working group's charter?  <br>
    </p>
    <p>The charter has language typical for revision efforts needing
      tight focus, seeking to limit changes and potential disruption for
      the installed base.  Specifically...<br>
    </p>
    <p>Emailcore Charter:<br>
    </p>
    <blockquote>
      <p><a moz-do-not-send="true"
          href="https://datatracker.ietf.org/doc/charter-ietf-emailcore/"
          class="moz-txt-link-freetext">https://datatracker.ietf.org/doc/charter-ietf-emailcore/</a><br>
      </p>
    </blockquote>
    <blockquote>
      <pre>This working group will conduct a limited review and revision to the base email specifications
... 
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.
...
However, no new protocol extensions or amendments will be considered

</pre>
    </blockquote>
    54 ticket items seems like quite a few, given the constraints.  As
    for changes to the SMTP specification, consider the diff between RFC
    5321 and latest rfc5321bis draft:<br>
    <blockquote>
      <p><a moz-do-not-send="true"
href="https://www.ietf.org/rfcdiff?url1=rfc5321&amp;url2=draft-ietf-emailcore-rfc5321bis-10">https://www.ietf.org/rfcdiff?url1=rfc5321&amp;url2=draft-ietf-emailcore-rfc5321bis-10</a><br>
      </p>
    </blockquote>
    <p>A few questions to consider:</p>
    <ul>
      <li>Are enough wg participants able and willing to justify every
        change, in detail, as conforming to the charter? Simply put, why
        were they essential, within the charter constraints?</li>
      <li>Given the number of changes, what is the basis for believing
        that an average reader will be able to apply the revised
        specification, while ensuring continued interoperability,
        especially given how creative readers can be with new text?<br>
      </li>
    </ul>
    <p>The concern is not whether any given change is broadly reasonable
      or a generally good idea, but whether it is essential to the
      immediate working group goal and within its charter?  <br>
    </p>
    <p>One could reasonably expect significant evidence of a problem
      that needs fixing, for each change.</p>
    <p><br>
    </p>
    <p>d/<br>
    </p>
    <pre class="moz-signature" cols="72">-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net</pre>
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On Tue, Mar 22, 2022 at 1:29 PM Dave Crocker <dhc@dcrocker.net> wrote:

> G'day,
>
> Seeing an email citing Ticket #54, as well as a new posting for
> rfc5321bis, I wonder whether all of the work being done on the revisions is
> within the working group's charter?
>
> The charter has language typical for revision efforts needing tight focus,
> seeking to limit changes and potential disruption for the installed base.
> Specifically...
>
> Emailcore Charter:
>
> https://datatracker.ietf.org/doc/charter-ietf-emailcore/
>
> This working group will conduct a limited review and revision to the base email specifications
> ...
> 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.
> ...
> However, no new protocol extensions or amendments will be considered
>
>
> 54 ticket items seems like quite a few, given the constraints.
>

Hatless...

I've understood the text I've been proposing for ticket 54 to be intended
for the Applicability Statement, not for 5321bis itself.

Does that change your opinion of the impact of this ticket on our adherence
to the charter?
-- 

*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 dir=3D"ltr"><div class=3D"gmail_default" style=3D"fon=
t-family:tahoma,sans-serif"><span style=3D"font-family:Arial,Helvetica,sans=
-serif">On Tue, Mar 22, 2022 at 1:29 PM Dave Crocker &lt;<a href=3D"mailto:=
dhc@dcrocker.net">dhc@dcrocker.net</a>&gt; wrote:</span><br></div></div><di=
v class=3D"gmail_quote"><blockquote class=3D"gmail_quote" style=3D"margin:0=
px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex">
 =20

   =20
 =20
  <div>
    <p>G&#39;day,</p>
    <p>Seeing an email citing Ticket #54, as well as a new posting for
      rfc5321bis, I wonder whether all of the work being done on the
      revisions is within the working group&#39;s charter?=C2=A0 <br>
    </p>
    <p>The charter has language typical for revision efforts needing
      tight focus, seeking to limit changes and potential disruption for
      the installed base.=C2=A0 Specifically...<br>
    </p>
    <p>Emailcore Charter:<br>
    </p>
    <blockquote>
      <p><a href=3D"https://datatracker.ietf.org/doc/charter-ietf-emailcore=
/" target=3D"_blank">https://datatracker.ietf.org/doc/charter-ietf-emailcor=
e/</a><br>
      </p>
    </blockquote>
    <blockquote>
      <pre>This working group will conduct a limited review and revision to=
 the base email specifications
...=20
The limited review is restricted to corrections and clarifications only, wi=
th a strong emphasis on keeping
these minimal and avoiding broader changes to terminology or document organ=
ization.
...
However, no new protocol extensions or amendments will be considered

</pre>
    </blockquote>
    54 ticket items seems like quite a few, given the constraints.=C2=A0</d=
iv></blockquote><div><br></div><div class=3D"gmail_default" style=3D"font-f=
amily:tahoma,sans-serif">Hatless...</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">I&#39;ve understood the text I&#39;v=
e been proposing for ticket 54 to be intended for the Applicability Stateme=
nt, not for 5321bis itself.</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">Does that change your opinion of the impact =
of this ticket on our adherence to the charter?</div><div class=3D"gmail_de=
fault" style=3D"font-family:tahoma,sans-serif"></div></div>-- <br><div dir=
=3D"ltr" class=3D"gmail_signature"><span><p dir=3D"ltr" style=3D"line-heigh=
t: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:sma=
ll;font-family:Arial"><b>Todd Herr </b></span><b></b><span style=3D"font-fa=
mily:Arial;font-size:small;white-space:pre-wrap"> | Technical Director, Sta=
ndards and Ecosystem</span></div><span style=3D"vertical-align:baseline;whi=
te-space:pre-wrap;font-size:small;font-family:Arial"><div style=3D"text-ali=
gn:left"><span style=3D"vertical-align:baseline"><b>e:</b></span><span styl=
e=3D"vertical-align:baseline"> <a href=3D"mailto:todd.herr@valimail.com" ta=
rget=3D"_blank">todd.herr@valimail.com</a> </span></div></span><span><div><=
span><b>m:</b></span><span> 703.220.4153</span><span></span></div><div styl=
e=3D"text-align:left"><img style=3D"width: 175px; height: 43px;" src=3D"htt=
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On 3/22/2022 11:07 AM, Todd Herr wrote:
> 
> Does that change your opinion of the impact of this ticket on our 
> adherence to the charter?


Todd, Since the concern I'm raising is general, it was the number, not 
the target.

I had in fact spent a moment of thought about doing a careful accounting 
for how many tickets applied to each working draft, but decided that 
that would be a distraction.

Look at the diff.  That's a lot of changes for a document with this 
charter's intent.  And it is not at all clear to me that all those 
changes are essential, within the confines of the charter.

d/
-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


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On Tue, Mar 22, 2022 at 2:34 PM Dave Crocker <dhc@dcrocker.net> wrote:

>
> Todd, Since the concern I'm raising is general, it was the number, not
> the target.
>
> I see. Thank you for the clarification.

-- 

*Todd Herr * | Technical Director, Standards and Ecosystem
*e:* todd.herr@valimail.com
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<div dir=3D"ltr"><div dir=3D"ltr"><div class=3D"gmail_default" style=3D"fon=
t-family:tahoma,sans-serif"><br></div></div><div class=3D"gmail_quote"><div=
 dir=3D"ltr" class=3D"gmail_attr">On Tue, Mar 22, 2022 at 2:34 PM Dave Croc=
ker &lt;<a href=3D"mailto:dhc@dcrocker.net">dhc@dcrocker.net</a>&gt; wrote:=
<br></div><blockquote class=3D"gmail_quote" style=3D"margin:0px 0px 0px 0.8=
ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><br>
Todd, Since the concern I&#39;m raising is general, it was the number, not =
<br>
the target.<br>
<br></blockquote><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
ans-serif"></div><div class=3D"gmail_default" style=3D"font-family:tahoma,s=
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v>-- <br><div dir=3D"ltr" class=3D"gmail_signature"><span><p dir=3D"ltr" st=
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On 22 Mar 2022, at 18:20, Dave Crocker wrote:

> https://www.ietf.org/rfcdiff?url1=3Drfc5321&url2=3Ddraft-ietf-emailcore=
-rfc5321bis-10
>
> A few questions to consider:
>
>   - Are enough wg participants able and willing to justify every =

> change, in detail, as conforming to the charter? Simply put, why were =

> they essential, within the charter constraints?
>   - Given the number of changes, what is the basis for believing that =

> an average reader will be able to apply the revised specification, =

> while ensuring continued interoperability, especially given how =

> creative readers can be with new text?
>
> The concern is not whether any given change is broadly reasonable or a =

> generally good idea, but whether it is essential to the immediate =

> working group goal and within its charter?=C2=A0

I certainly think it's a good idea to go through the diff and make sure =

that we agree with the changes being made and that they are really =

needed. Interestingly (to me), I just did a quick run-through of the =

diff above and I was surprised with how *few* changes there actually =

were in the document. Lots (most?) of the changes are changed reference =

numbers, different spacing, or a moved paragraph or two; there were less =

substantive changes than I had remembered. But on this suggestion, I =

definitely will set aside some time to do a thorough review with the "is =

this necessary" mantra in mind.

That said, as per RFC 2418 3.3, it is in the end the chairs' call =

whether any suggested change is within or out of scope of the charter. =

I'm willing to presume they have been paying attention enough to have =

called out anything that they noticed out of scope already, bit it's =

certainly it's reasonable for any of us to ask the chairs to review any =

particular change with regard to scope, and they may ask for =

justification. And it's also reasonable to disagree with the chairs' =

call on that call and appeal to the AD (etc.) if needed. But I don't =

think we need to do some special collection of justifying "significant =

evidence" for each change unless some question is raised about it that =

hasn't already been reviewed.

pr
-- =

Pete Resnick https://www.episteme.net/
All connections to the world are tenuous at best

--=_MailMate_006B455F-0053-450B-8087-F8C09275B53B_=
Content-Type: text/html; charset=UTF-8
Content-Transfer-Encoding: quoted-printable

<!DOCTYPE html>
<html>
<head>
<meta http-equiv=3D"Content-Type" content=3D"text/xhtml; charset=3Dutf-8"=
>
</head>
<body><div style=3D"font-family: sans-serif;"><div class=3D"markdown" sty=
le=3D"white-space: normal;">
<p dir=3D"auto">On 22 Mar 2022, at 18:20, Dave Crocker wrote:</p>
</div><div class=3D"plaintext" style=3D"white-space: normal;"><blockquote=
 style=3D"margin: 0 0 5px; padding-left: 5px; border-left: 2px solid #777=
777; color: #777777;"><p dir=3D"auto"><a href=3D"https://www.ietf.org/rfc=
diff?url1=3Drfc5321&amp;url2=3Ddraft-ietf-emailcore-rfc5321bis-10" style=3D=
"color: #777777;">https://www.ietf.org/rfcdiff?url1=3Drfc5321&amp;url2=3D=
draft-ietf-emailcore-rfc5321bis-10</a></p>
<p dir=3D"auto">A few questions to consider:</p>
<p dir=3D"auto">  - Are enough wg participants able and willing to justif=
y every change, in detail, as conforming to the charter? Simply put, why =
were they essential, within the charter constraints?
<br>
  - Given the number of changes, what is the basis for believing that an =
average reader will be able to apply the revised specification, while ens=
uring continued interoperability, especially given how creative readers c=
an be with new text?</p>
<p dir=3D"auto">The concern is not whether any given change is broadly re=
asonable or a generally good idea, but whether it is essential to the imm=
ediate working group goal and within its charter?=C2=A0</p>
</blockquote></div>
<div class=3D"markdown" style=3D"white-space: normal;">
<p dir=3D"auto">I certainly think it's a good idea to go through the diff=
 and make sure that we agree with the changes being made and that they ar=
e really needed. Interestingly (to me), I just did a quick run-through of=
 the diff above and I was surprised with how <em>few</em> changes there a=
ctually were in the document. Lots (most?) of the changes are changed ref=
erence numbers, different spacing, or a moved paragraph or two; there wer=
e less substantive changes than I had remembered. But on this suggestion,=
 I definitely will set aside some time to do a thorough review with the &=
quot;is this necessary&quot; mantra in mind.</p>
<p dir=3D"auto">That said, as per RFC 2418 3.3, it is in the end the chai=
rs' call whether any suggested change is within or out of scope of the ch=
arter. I'm willing to presume they have been paying attention enough to h=
ave called out anything that they noticed out of scope already, bit it's =
certainly it's reasonable for any of us to ask the chairs to review any p=
articular change with regard to scope, and they may ask for justification=
=2E And it's also reasonable to disagree with the chairs' call on that ca=
ll and appeal to the AD (etc.) if needed. But I don't think we need to do=
 some special collection of justifying &quot;significant evidence&quot; f=
or each change unless some question is raised about it that hasn't alread=
y been reviewed.</p>
<p dir=3D"auto">pr</p>
<p dir=3D"auto">--<br>
Pete Resnick <a href=3D"https://www.episteme.net/" style=3D"color: #3983C=
4;">https://www.episteme.net/</a><br>
All connections to the world are tenuous at best</p>

</div></div></body>

</html>

--=_MailMate_006B455F-0053-450B-8087-F8C09275B53B_=--


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On 3/23/2022 7:42 AM, Pete Resnick wrote:
> But I don't think we need to do some special collection of justifying 
> "significant evidence" for each change unless some question is raised 
> about it that hasn't already been reviewed.


That is, at base, a 'default yes' model.  A charter with these kinds of 
constraints, typically benefits from a much more active consideration 
whether each possible change is within scope.

I haven't done an audit, but it has seemed to me that consideration of 
scope has been rather more erratic than that.

d/
-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


From nobody Thu Mar 24 01:59:51 2022
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From: Pete Resnick <resnick@episteme.net>
To: dcrocker@bbiw.net
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On 23 Mar 2022, at 17:11, Dave Crocker wrote:

> On 3/23/2022 7:42 AM, Pete Resnick wrote:
>> But I don't think we need to do some special collection of justifying 
>> "significant evidence" for each change unless some question is raised 
>> about it that hasn't already been reviewed.
>
>
> That is, at base, a 'default yes' model.

Not at all. As I said, I've been presuming that the chairs have been 
doing their job by defaulting "no" to changes. I've certainly seen a 
consistent pattern of that, both from the chairs and from WG 
participants. So I don't think there's much of a reason to believe that 
we've made some big mistake along these lines.

> A charter with these kinds of constraints, typically benefits from a 
> much more active consideration whether each possible change is within 
> scope.

And I agree, again from my earlier message, that it would be prudent for 
each of us to re-read, with diff in hand, to make sure we believe that 
the due diligence was done. The thing that I don't see as necessary is 
what I took to be your proposal for that review to be so formal as to 
have documentation of "significant evidence" that each change met the 
appropriate charter criteria. We've had plenty of WGs in the past with 
very constrained charters and I've never heard of us doing that formal 
of an audit.

> I haven't done an audit, but it has seemed to me that consideration of 
> scope has been rather more erratic than that.

Not my impression, but a sanity check is always a good thing.

pr

-- 
Pete Resnick https://www.episteme.net/
All connections to the world are tenuous at best


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Subject: Re: [Emailcore] RCPT commands, BCCs, and the "for" clause
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--On Tuesday, March 22, 2022 15:08 +0100 Alexey Melnikov
<aamelnikov@fastmail.fm> wrote:

> Hi John,
> (Replying as a WG participant)
> 
>> On 22 Mar 2022, at 14:22, John C Klensin <john-ietf@jck.com>
>> wrote:


>> The second conclusion is that RFC 5321 says rather more about
>> these topics than it should and that we are trying to fix the
>> issues that text causes by adding more text and risking even
>> more confusion (in other words, trying to get out of the hole
>> by digging deeper). With the understanding that none of the
>> ideas below are new except for the organization and context,
>> my current hunch is that 5321bis should:
>> 
>> (i) Remind people that a conforming SMTP server or
>> (non-submission) client doesn't look at header fields, much
>> less start performing heuristics on them, and hence does not
>> have a clue as to which RCPT commands (or their arguments) are
>> associated with "To:", "Cc:", or "Bcc:" header fields.
>> Section 7.8 provides a loophole for, e.g., malware resistance
>> measures, but does not change the principle.
>> 
>> (ii) Mention that no attempt should be made to include "for"
>> in a "Received:" header field if there is more than one RCPT
>> command present, noting that this is forbidden by the syntax
>> anyway.
> 
> I think this statement is stronger than currently specified in
> the draft and is not something I agree. If a message has 2
> RCPT TO recipients A and B (let's assume for simplicity that
> A and B are end user email addresses, not mailing lists), I
> think it is perfectly ok to do either:
> 
> 1) The same message with Received with no FOR is delivered to
> both A and B
> 
>  or
> 
> 2) Recipient A receives a copy of the message with Received
> with FOR A, while recipient B receives a copy of the message
> with Received with FOR B.
> 
> Your statement (ii) prevents choice 2)

I think we are thinking about different parts of the relay
chain.  For the server that is inserting a "Received:" header
just before making final delivery, you are absolutely correct.
The "for" clause of that trace field is, I think, also fairly
useless unless some post-delivery process makes changes to the
recipient address.  However, assume DNS records that look like

   example1.com.   MX 5 relay1.example.
   example1.com.   MX 2 relay2.example.
   example1.com.   MX 0 deliveryServer1.example1.com.
   example2.com.   MX 5 relay1.example.
   example2.com.   MX 0 deliveryServer2.example2.com.

Also assume the message in question leaves the MSA with
    RCPT TO:<tom@example1.com>
    RCPT TO:<dick@example1.com>
    RCPT TO:<harry@example2.com>

Now, assuming the two deliveryServers and relay2 are not
answering when the MSA asks and that the MSA does not decide to
send three separate messages on principle, relay1 gets a single
mail transaction with the RCPT commands above.    So, question 1
is what, if any, it puts in the "for" clause of the trace field
it adds given that it has three possible target mailbox
addresses?  Statement (ii) above says "no for clause" but I'm
listening for other options that clarify RFC 5321 rather than
making substantive changes.

Now, it (relay1) notices that the message contains domains with
two different next-hop MX preferences (again assuming that
deliveryServer1 is not being responsive).  It opens a connection
to relay2 with a mail transaction specifying 
 
    RCPT TO:<tom@example1.com>
    RCPT TO:<dick@example1.com> 

Question 2 is what relay2 puts in the "for" clause of the trace
field it generates.  It still has a choice of two addresses and,
as far as it is concerned, it is delivering one message to both.
It opens a mail transaction to deliveryServer1, which, assuming
it actually delivers separately to the two mailboxes (your
case), generates a trace header for each that differs only in
the "for" clause.  FWIW, if deliveryServer1 hands off to a
separate MDA (a distinction RFC 5321 does not recognize) that
splits the messages up on a per-mailbox basis and deposits them
in the mail store (something else 5321 at best hand waves
about), it has the same problem as relay2 and cannot split the
"for" clauses either.

deliveryServer2 of course has it easier.  It gets only one
recipient from relay1, harry@example2.com, puts that in the
"for" clause in the trace field it generates, and delivers the
message to that mailbox.

And, of course, if there were any way for relay1 to write a
"for" clause with more than one RCPT command, tom, dick, and
harry would all find out about the others unless the respective
delivery servers edited those additional "for" subclauses out.
5321 forbids both multiple addresses per "for" clause and
editing of trace fields by servers later in the chain, so that
is, fortunately, a non-issue.

So, my statement of the options (I did say "hunch" and not
"conclusion" :-)) was clearly not correct and is in need of
fixing (at least).  On the other hand, your choice 2 is possible
only for the MTA that splits multiple-recipient messages into
individual ones, presumably for delivery.

>> (iii) Clarify the text that mentions that "for" can cause
>> unintended privacy disclosures and say that, if one is not
>> sure of the appropriateness of the clause and the information
>> that should go into it, it is generally better to just omit
>> the clause.

> Agreed.
 
>> (iv) Mention as well that _any_ trace field might, under the
>> wrong set of circumstances, disclose information that someone
>> might consider sensitive and that, while those fields are
>> often essential for debugging messages that have run into
>> transport problems and may even be helpful in distinguishing
>> spoofed or otherwise problematic messages from more desirable
>> traffic (and even identifying the source of such bad
>> traffic), complete protection of anything that might be
>> considered private would argue for eliminating trace
>> information entirely.
 
> Agreed.

>> Wordsmithing and some decisions about where to use 2119/8174
>> language obviously needed, but I'm hoping we can agree on the
>> above or something like it as general principles.
>> 
>> We then get rid of all of the hair-splitting about internal
>> names and addresses on LANs, which addresses should be
>> included in "for" clauses and which ones avoided, etc.  If
>> someone believes they can persuade the WG that it is worth
>> doing the case analysis and offering more specific advice in
>> the A/S they should certainly try (and be ready to write
>> text).  But, as far as 5321bis is concerned, my
>> recommendation is that we concentrate on the above four
>> points and tear everything else out.  That would, IMO,
>> improve clarity and and shorten 5321bis by a few pages.
 
> I am personally Ok with this direction, but I think I would
> like to see the new proposed text before fully committing to
> it. Is it something you can post to the mailing list before
> Friday or at least soon-ish?

Obviously, no, since it is Friday already (busy week).  Up to
you, in your chair capacity, to decide whether we should discuss
in circa seven hours or just defer the whole topic for the
mailing list.  My personal preference would be to see if we can
get general agreement on the approach and then sort text out on
the mailing list but, again, up to you.

best,
   john


From nobody Thu Mar 24 22:12:43 2022
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Date: Fri, 25 Mar 2022 01:12:29 -0400
From: John C Klensin <john-ietf@jck.com>
To: John Levine <johnl@taugh.com>, emailcore@ietf.org
cc: "Murray S. Kucherawy" <superuser@gmail.com>
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Subject: Re: [Emailcore] Relaxing the IANA registration requirement for SMTP Extensions in rfc5321bis
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--On Tuesday, March 22, 2022 12:38 -0400 John Levine
<johnl@taugh.com> wrote:

> It appears that John C Klensin  <john-ietf@jck.com> said:
>> keyword accidentally being used for different things, I'm in
>> favor of relaxing the requirements somewhat from Standards
>> Track or IESG-approved Experimental.
> 
> My inclination is somewhere between specification required and
> expert review, with the understanding that the point of the
> review is just to see that the specification is at least
> superficially plausible.  We have our share of unused
> extensions (MTRK, CONNEG, ...) and I'm not worried that there
> is a flood of worse ones waiting.

The cases that have gotten me concerned are variations of some
of the recent discussions about media types.  RFC 8494 opened
the door to specialized uses of SMTP, uses that an Expert or
Expert team might not fully understand.  While 8494 (IMO) does
not have that problem and does not introduce any new extensions
(as far as the extension system is concerned, it is basically a
profile).  I don't think it is hard to imagine some specialized
use coming along that involves a new extension or two for which
the descriptions could be entirely plausible but
incomprehensible to most of us.  My instinct is that figuring
out a way to do a community Last Call in conjunction with Expert
Review -- Murray and I have kicked that back and forth a bit and
probably the right way to do it is to stick with IESG review but
involve the Designated Reviewers in the evaluation of the
document and the Last Call and have the IESG's role be mostly
pro-forma.

>> Suggestion: RFC 5321 Section 8, IANA Considerations, describes
>> the three registries but does not actually specify what goes
>> in them, nor does it follow what is now the normal practice of
>> providing a specific registration template or list of fields
>> and descriptions of possible values [1].  For the SMTP
>> Extensions Registry, we should consider either specifying a
>> template or a list of things required in an application for a
>> Service Extension.

> That would be a good idea.  Yesterday Alexey and I realized
> that 5321 says VRFY is a service extension that somehow never
> made it into the registry.

I think that is a separate problem.  I wish 5321 was more clear
(and hope we can fix that) but VRFY support is (modulo the usual
loopholes) required by 5321 but still required to be listed in
EHLO responses.   That makes it a required feature that is
treated as a service extension (and, if you and Alexey found
statements that seem to contradict other statements... well, I
would not be terribly surprised). From the standpoint of the
registry, especially in the days when there was no such thing as
a required extension, that means is it not an extension at all
and should not be listed.  From the standpoint of common sense
and minimization of confusion, it should clearly be in the
registry, perhaps with a brief note.

best,
   john


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From: Dave Crocker <dhc@dcrocker.net>
Organization: Brandenburg InternetWorking
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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On 3/22/2022 7:29 AM, Todd Herr wrote:
> 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.


Authentication is the process of validating an asserted identity of one or
more of the endpoints of a communication channel. TLS usage typically 
only attempts authentication of the server side of the communication 
channel;
authentication of the client side is optional. Further, 'opportunistic' 
use of TLS offers a somewhat fragile form of authentication.


d/


-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net


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From: Dave Crocker <dcrocker@gmail.com>
To: EmailCore WG <emailcore@ietf.org>
Archived-At: <https://mailarchive.ietf.org/arch/msg/emailcore/6dryxE1MzxJUKOlhn2e9L7HKNo0>
Subject: [Emailcore] sub-addressing
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A propos the reference to sub-addressing at the end of the wg session:


RFC 5598, Section 3.1:

> It is common for sites to have local structuring conventions for the
>     left-hand side, <local-part>, of an <addr-spec>.  This permits sub-
>     addressing, such as for distinguishing different discussion groups
>     used by the same participant.  However, it is worth stressing that
>     these conventions are strictly private to the User's organization and
>     are not interpreted by any domain except the one listed in the right
>     side of the <addr-spec>.  The exceptions are those specialized
>     services that conform to public, standardized conventions, as noted
>     below.
>
>     Basic email addressing defines the <local-part> as being globally
>     opaque.  However, there are some uses of email that add a
>     standardized, global schema to the value, such as between an Author
>     and a Gateway.  The <local-part> details remain invisible to the
>     public email transfer infrastructure, but provide addressing and
>     handling instructions for further processing by the Gateway.
>     Standardized examples of these conventions are the telephone
>     numbering formats for the Voice Profile for Internet Mail (VPIM)
>     [RFC3801  <https://www.rfc-editor.org/rfc/rfc3801>], such as:
>
>                         +16137637582@vpim.example.com,
>
>     and iFax ([RFC3192  <https://www.rfc-editor.org/rfc/rfc3192>], [RFC4143  <https://www.rfc-editor.org/rfc/rfc4143>] such as:
>
>                  FAX=+12027653000/T33S=1387@ifax.example.com.

-- 
Dave Crocker
dcrocker@gmail.com
408.329.0791

Volunteer, Silicon Valley Chapter
Information & Planning Coordinator
American Red Cross
dave.crocker2@redcross.org

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<html>
  <head>

    <meta http-equiv="content-type" content="text/html; charset=UTF-8">
  </head>
  <body>
    <p>A propos the reference to sub-addressing at the end of the wg
      session:</p>
    <p><br>
    </p>
    <p>RFC 5598, Section 3.1:</p>
    <p>
      <blockquote type="cite">
        <pre class="newpage">It is common for sites to have local structuring conventions for the
   left-hand side, &lt;local-part&gt;, of an &lt;addr-spec&gt;.  This permits sub-
   addressing, such as for distinguishing different discussion groups
   used by the same participant.  However, it is worth stressing that
   these conventions are strictly private to the User's organization and
   are not interpreted by any domain except the one listed in the right
   side of the &lt;addr-spec&gt;.  The exceptions are those specialized
   services that conform to public, standardized conventions, as noted
   below.

   Basic email addressing defines the &lt;local-part&gt; as being globally
   opaque.  However, there are some uses of email that add a
   standardized, global schema to the value, such as between an Author
   and a Gateway.  The &lt;local-part&gt; details remain invisible to the
   public email transfer infrastructure, but provide addressing and
   handling instructions for further processing by the Gateway.
   Standardized examples of these conventions are the telephone
   numbering formats for the Voice Profile for Internet Mail (VPIM)
   [<a href="https://www.rfc-editor.org/rfc/rfc3801" title="&quot;Voice Profile for Internet Mail - version 2 (VPIMv2)&quot;">RFC3801</a>], such as:

                       +16137637582@vpim.example.com,

   and iFax ([<a href="https://www.rfc-editor.org/rfc/rfc3192" title="&quot;Minimal FAX address format in Internet Mail&quot;">RFC3192</a>], [<a href="https://www.rfc-editor.org/rfc/rfc4143" title="&quot;Facsimile Using Internet Mail (IFAX) Service of ENUM&quot;">RFC4143</a>] such as:

                <a class="moz-txt-link-abbreviated" href="mailto:FAX=+12027653000/T33S=1387@ifax.example.com">FAX=+12027653000/T33S=1387@ifax.example.com</a>.</pre>
      </blockquote>
      <br>
    </p>
    <pre class="moz-signature" cols="72">-- 
Dave Crocker
<a class="moz-txt-link-abbreviated" href="mailto:dcrocker@gmail.com">dcrocker@gmail.com</a>
408.329.0791

Volunteer, Silicon Valley Chapter
Information &amp; Planning Coordinator
American Red Cross
<a class="moz-txt-link-abbreviated" href="mailto:dave.crocker2@redcross.org">dave.crocker2@redcross.org</a></pre>
  </body>
</html>

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From nobody Fri Mar 25 12:26:53 2022
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From: Pete Resnick <resnick@episteme.net>
To: dcrocker@bbiw.net
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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On 25 Mar 2022, at 14:04, Dave Crocker wrote:

> Further, 'opportunistic' use of TLS offers a somewhat fragile form of 
> authentication.

I don't think that's quite correct. In one set of cases, opportunistic 
TLS provides absolutely no form of authentication (as the text Todd 
provided explains). In the other set of cases (opportunistic DANE TLS), 
you get solid authentication. Calling that combination "fragile" seems 
inaccurate. I'd rather leave off this extra sentence and leave it to 
sections 5.1 and 5.2 to explain what's available.

pr

-- 
Pete Resnick https://www.episteme.net/
All connections to the world are tenuous at best


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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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It appears that Pete Resnick  <resnick@episteme.net> said:
>On 25 Mar 2022, at 14:04, Dave Crocker wrote:
>
>> Further, 'opportunistic' use of TLS offers a somewhat fragile form of 
>> authentication.
>
>I don't think that's quite correct. In one set of cases, opportunistic 
>TLS provides absolutely no form of authentication (as the text Todd 
>provided explains). In the other set of cases (opportunistic DANE TLS), 
>you get solid authentication.

Don't forget MTA-STS (RFC 8461) which provides more or less the same
thing as DANE TLS in a klunkier way. If you use DANE and MTA-STS in
enforce mode I agree you get solid server authentication, give or take how
widely implemented they are.

R's,
John


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Todd,

This comment may partially relate to the discussion among Dave,
Pete, and John, but my concern is a bit different.  While
someone who knows what to look for and is reading carefully will
figure it out, I think it is very important that you make two
distinctions explicitly:

(1) Putting S/MIME and PGP aside, none of these techniques, at
least as I understand them, offer user/sender level
authentication.  Those that provide authentication authenticate
hosts, not users, and some provide integrity protection to part
or all of the message (integrity protection is the third part of
the puzzle and should probably be mentioned along with
authentication and confidentiality).  They _may_ authorize
particular users or mailboxes to send mail, but do not
authenticate the users themselves.  These distinctions should be
made clear.

(2) Again putting S/MIME and PGP aside, confidentially for these
methods is strictly hop by hop, with messages in clear on
relays.  Put more strongly, if servers can easily be attacked,
protecting messages in transit between them does not help much.
And these procedures do not provide endpoint to endpoint
confidentiality.

In addition, your Section 5.5 on S/MIME and PGP should note
that, properly used and with the right options, they provide not
only endpoint-to-endpoint confidentiality of message content but
strong authentication of sending users (not just mailboxes) and
message body integrity.

Finally, I question dismissing S/MIME and PGP on the grounds
that they "operate fully independent of SMTP".  Certainly that
is true.  But, when SMTP runs over a security layer (such as TLS
or even SSH) that security layer is operating fully independent
of SMTP too.   I don't have a serious problem with your
explaining them briefly and then saying "out of scope", but I
think you need a better explanation.

   john


--On Tuesday, March 22, 2022 10:29 -0400 Todd Herr
<todd.herr=40valimail.com@dmarc.ietf.org> wrote:

> Greetings.
> 
> I've reviewed the comments generated by my posting rev 3 here
> at the end of January, and I've incorporated some of them.
> 
> The one that I didn't incorporate was one that Dave Crocker
> made to perhaps discuss the concepts of Channel Security
> versus Object Security in section 5.5, Message-Level
> Confidentiality. While I thought the suggestion had merit on
> its face, the fact that the section is just a paragraph talking
> about how OpenPGP and S/MIME (and similar technologies) are
> out of scope for the A/S made me decide not to add more text
> to this section.
> 
> Current revision follows, there's a place in the agenda to
> discuss it during Friday's meeting.
> 
> =========================== cut here ========================
> 
> A/S Proposed Text - Confidentiality and Authentication
> 
> 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 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
> 
> 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 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 the 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.
> 
> 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. Its name might suggest that it would
> be within scope for this section of the Applicability
> Statement, but in fact it's not.
> 
> 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 ========================



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From: "John Levine" <johnl@taugh.com>
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It appears that John C Klensin  <john-ietf@jck.com> said:
>Finally, I question dismissing S/MIME and PGP on the grounds
>that they "operate fully independent of SMTP".  Certainly that
>is true.  But, when SMTP runs over a security layer (such as TLS
>or even SSH) that security layer is operating fully independent
>of SMTP too.  ...

When the client uses DANE or MTA-STS, it's using TLS to verify that
the SMTP server is the one it expects to be talking to. I don't think
that's outside of SMTP, and it seems quite different from S/MIME.

I do agree that the threats and mitigations could be matched up better.

R's,
John

PS: I suppose I should send text.


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--On Saturday, March 26, 2022 10:25 -0400 John Levine
<johnl@taugh.com> wrote:

> It appears that John C Klensin  <john-ietf@jck.com> said:
>> Finally, I question dismissing S/MIME and PGP on the grounds
>> that they "operate fully independent of SMTP".  Certainly that
>> is true.  But, when SMTP runs over a security layer (such as
>> TLS or even SSH) that security layer is operating fully
>> independent of SMTP too.  ...
> 
> When the client uses DANE or MTA-STS, it's using TLS to verify
> that the SMTP server is the one it expects to be talking to. I
> don't think that's outside of SMTP, and it seems quite
> different from S/MIME.

That is fair.  I was thinking much more about backward
(sender-side) authentication (of sending users, and sender-SMTP
hosts) than about forward authentication of receiver-SMTP hosts.
Our apparent disagreement is, IMO, more reinforcement for the
idea that the document should be far more clear about exactly
what it is talking about and where.

> I do agree that the threats and mitigations could be matched
> up better.

Yeah.

  thanks,
    john


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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On Sat, 26 Mar 2022, John C Klensin wrote:
>> When the client uses DANE or MTA-STS, it's using TLS to verify
>> that the SMTP server is the one it expects to be talking to. ...
>
> That is fair.  I was thinking much more about backward
> (sender-side) authentication (of sending users, and sender-SMTP
> hosts) than about forward authentication of receiver-SMTP hosts.

I have seen code that does client authentication with client certs, but 
to the extent it even exists, it's definitely submission, not SMTP.

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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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On Sat, Mar 26, 2022, John R Levine wrote:

> I have seen code that does client authentication with client certs, but to
> the extent it even exists, it's definitely submission, not SMTP.

sendmail can enforce client authentication via certs in SMTP
and it is being used as such (based on data I've seen).

-- 
Address is valid for this mailing list only, please do not reply
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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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Claus Assmann wrote in
 <20220326192521.GA3224@veps.esmtp.org>:
 |On Sat, Mar 26, 2022, John R Levine wrote:
 |> I have seen code that does client authentication with client certs, \
 |> but to
 |> the extent it even exists, it's definitely submission, not SMTP.
 |
 |sendmail can enforce client authentication via certs in SMTP
 |and it is being used as such (based on data I've seen).

Even though Viktor Dukhovni is here .. i was also using client
certificates with postfix.  (And SMTPS, so it is possible.  In
fact i always have a hard time seeing the difference except for
the dedicated configuration that listens on a dedicated socket.
=46rom my own dumb user point of view i connect to SMTPS:465.)

--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)


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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On 26/03/2022 19:52, Steffen Nurpmeso wrote:
> Claus Assmann wrote in
>   |sendmail can enforce client authentication via certs in SMTP
>   |and it is being used as such (based on data I've seen).
> 
>  i was also using client
> certificates with postfix.
As can Exim, likewise orthogonal to port number and STARTTLS
vs. on-connect.  So that's a full triple of "the independents".
-- 
Cheers,
   Jeremy


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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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It appears that Claus Assmann  <emailcore@ietf.org> said:
>On Sat, Mar 26, 2022, John R Levine wrote:
>
>> I have seen code that does client authentication with client certs, but to
>> the extent it even exists, it's definitely submission, not SMTP.
>
>sendmail can enforce client authentication via certs in SMTP
>and it is being used as such (based on data I've seen).

I believe the code is there and someone is using it, but I'm having trouble
figuring out how one would use it for SMTP rather than submission.  If you only 
accept mail from hosts that provide certs that you like, you're not much of an
SMTP server.

(Note that you can do submission on port 25.)

R's,
John


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On 26/03/2022 20:18, John Levine wrote:
> If you only
> accept mail from hosts that provide certs that you like, you're not much of an
> SMTP server.

Maybe you do both forwarding (for a limited set of authenticating senders)
and reception-and-delivery (from anywhere)?

But perhaps you want to declare that the former is submission.  I don't
have the energy to argue.
-- 
Cheers,
   Jeremy


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Jeremy Harris wrote in
 <ccc027ee-002d-28c0-e2c6-36ae629ea7de@wizmail.org>:
 |On 26/03/2022 20:18, John Levine wrote:
 |> If you only
 |> accept mail from hosts that provide certs that you like, you're not \
 |> much of an
 |> SMTP server.
 |
 |Maybe you do both forwarding (for a limited set of authenticating senders)

The postfix camp says relay policy.

 |and reception-and-delivery (from anywhere)?
 |
 |But perhaps you want to declare that the former is submission.  I don't
 |have the energy to argue.

Aye.

--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)


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It appears that Jeremy Harris  <jgh@wizmail.org> said:
>On 26/03/2022 20:18, John Levine wrote:
>> If you only
>> accept mail from hosts that provide certs that you like, you're not much of an SMTP server.
>
>Maybe you do both forwarding (for a limited set of authenticating senders)
>and reception-and-delivery (from anywhere)?

Good point.  This gets us into nitipicky arguments about submission vs smarthost vs SMTP,
which I think are best discussed not very much.

R's,
John


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--On Saturday, March 26, 2022 20:29 +0000 Jeremy Harris
<jgh@wizmail.org> wrote:

> On 26/03/2022 20:18, John Levine wrote:
>> If you only
>> accept mail from hosts that provide certs that you like,
>> you're not much of an SMTP server.
> 
> Maybe you do both forwarding (for a limited set of
> authenticating senders)
> and reception-and-delivery (from anywhere)?
> 
> But perhaps you want to declare that the former is submission.
> I don't have the energy to argue.

Jeremy,

Not to argue (but perhaps to agree instead)... The problem is
that, if the former (or a bunch of other odd cases) are
submission, then we open a can of something nastier than worms.
As you know, issues about port selection, whatever one thinks of
RFC 8314 [1], and other small details aside, the key difference
between submission and "normal" SMTP is that we allow (and
encourage) submission servers to do all sorts of things to fix
up whatever garbage MUAs send them and make the messages fit for
sending across the public Internet... even including potentially
applying S/MIME or PGP.  We forbid all of that to normal SMTP
MTAs, so declaring the kind of forwarding you describe as
submission would be really bad news.

John Levine and others,

One thing that tends to get lost in these discussions is that
there are many uses of SMTP for special applications, even when
those applications run over the public Internet.  If the
operators of a receiver-SMTP (delivery server or not), knows
that it should be receiving traffic only from a restricted set
of sender-SMTP systems and consider the traffic or its possible
consequences at all sensitive, it becomes reasonable and
appropriate for them to insist on more or less strong
authentication of either the sending user (S/MIME or PGP cases,
but they require accepting the message and looking at its
content)  or the previous-hop sender-SMTP.  Over the years I've
seen efforts at authentication of the former using many options
including checking the connection attempt against a list of
permitted IP addresses, magic cookies in the HELO/EHLO command
or tricks with the MAIL command (most often involving use of
trick local-parts), requiring that SMTP run over SSH and doing
some handshaking before the actual mail session is established,
and client cert checking.  

I think it would be unnecessary and unwise for the A/S to
explain those cases in any detail or spend non-trivial time on
them more generally.  But I think it is important that it be
written with enough awareness of them that we do not
accidentally prohibit, or even say nasty things about, cases
that are perfectly reasonable under the right circumstances.
And, repeating something I've tried to say before in the last 48
hours, it is extremely important that the document be very clear
about what it is talking about and, in particular, avoid talking
about authentication without being clear who or what is being
authenticated and to what or who.

best,
   john

[1]  Translation of the implicit snarky comment, noting that
Submission being out of scope for the WG takes 8314 out of scope
too (and IMAP, POP, etc., are even more so):  When the
Submission Server is being run by a conventional MSP on the
public Internet and separated from and serving multiple MUAs,
8314 makes perfect sense.  However, when the two are both
operating on a well-secured enterprise LAN or the connection
between the two is being run over a well-secured connection
(e.g., SSH or even IPv6 link encryption with the server refusing
to accept unencrypted connections), the MSA server sees only
cleartext but forcing running TLS over such connections is
almost certainly going to be a waste of time and energy with
nearly zero improved security.  Similar comments can be made on
the Mail Access (POP/IMAP) side of things.  I'm mentioning this
only because it is another case of assuming that the most common
cases are the only ones and then writing specifications
accordingly.  We really need to be more careful about that.







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Subject: Re: [Emailcore] Ticket #54 - Authentication and Encryption for A/S - Rev. 4
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On Sat, Mar 26, 2022, John Levine wrote:

> figuring out how one would use it for SMTP rather than submission.  If you only 

By selectively enforcing it for "well known" hosts (or even domains).
There are different "levels" of requirements, so admins can decide
whether to require a cert that can be "verified", a specific cert
issuer, or even stronger restrictions.

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On 3/25/2022 12:26 PM, Pete Resnick wrote:
> On 25 Mar 2022, at 14:04, Dave Crocker wrote:
> 
>> Further, 'opportunistic' use of TLS offers a somewhat fragile form of 
>> authentication.
> 
> I don't think that's quite correct. In one set of cases, opportunistic 
> TLS provides absolutely no form of authentication (as the text Todd 
> provided explains).


So, this prompted some exploration, which mostly created more confusion.

My comment came from an extended wg discussion which, I think, produced 
RC 7435 (Opportunistic Security: Some Protection Most of the Time).

I took the goal of such work to be finding ways to get encryption, 
without needing a global cert system.  This would seem to support the 
view that opportunistic encryption, such as with TLS, doesn't do 
authentication.

Opportunistic TLS appears to have two different goals.  One is to invoke 
TLS after the start of the application session, via starttls.  The 
second is the one that lets encryption work without a global cert.

This latter one is what my comment was intended to refer to.  And sure, 
in the abstract, encryption requires a public key for the target, not an 
authenticated identity.

However consider that servers often provide self-signed certs.  These 
are the cases I intended in my comment.  They are offering an identifier 
and they are self-authenticating it.

That is, in practice, my understanding is that TLS provides encryption 
by anchoring it to a proffered identifier.  Even an ad hoc one.


d/



-- 
Dave Crocker
Brandenburg InternetWorking
bbiw.net

