I don't think DKIM2 helps at all in that case.

A sender is well within their rights to put in a new header that specifies
the set of recipients for the message, if they were so inclined. And that's
assuming the recipients aren't already listed in destination address
headers (To/Cc) which seems to be the case in the linked example.

Having all recipients listed in a DKIM2 signature's rt= tag gives no more
guarantee that the signer actually did what it claimed it was going to do
than any other header. In the case of having a single recipient in the rt=
tag, there's no advantage to claiming that a message is being sent
somewhere other than the 821.To for that transaction, since the receiving
server is expected to treat this as not DKIM2-authenticated.

On Thu, Mar 20, 2025 at 12:48 PM Alessandro Vesely <ves...@tana.it> wrote:

> On Wed 19/Mar/2025 17:22:06 +0100 Michael Thomas wrote:
> > On 3/18/25 12:30 PM, Richard Clayton wrote:
> >> In message <746bd827-77d0-4991-ba67-507d84566...@mtcc.com>, Michael
> >> Thomas <m...@mtcc.com> writes
> >>>>>>
> >>>>>> simplicity ... at the point at which an email is being signed it is
> not
> >>>>>> possible to know how many recipients the receiving MTA will accept
> after
> >>>>>> each MAIL FROM
> >>>>>
> >>>>> Why is that "simple"?
> >>>>
> >>>> because if you don't know which recipients will be grouped together
> you
> >>>> cannot construct the rt= part of the DKIM2 header field. It also
> avoids
> >>>> the MTA having to assess which recipients are only bcc'd
> >>>
> >>> I dunno, if the To: header is all to the same domain, say, and they
> match the
> >>> rcpt-to like with an email conversation, you know that it's safe to
> group
> >>> them.
> >>
> >> when you get to SMTP time you may find that you are sending multiple
> >> emails (because of limitations on RCPT TO counts) and those emails may
> >> not go to the same server ... so how is the recipient going to do any
> >> sensible assessment of whether a replay has occurred ?
> >
> > The point here is that if an implementation can figure out how to do
> that, the
> > implementation should have that option. If the easiest way is to just do
> single
> > address rcpt-to's, that's fine but it doesn't require a protocol level
> MUST to
> > forbid multiple addresses on the rcpt-to. It would be fine to add some
> > informative text as to why a single address is easier, but it doesn't
> need to
> > enforced at the protocol level.
>
>
> Accommodating multiple recipients in the signature would have the added
> value
> of confirming to whom a message is destined.  There are companies that
> need to
> certify to each recipient who the other recipients of a message are.  A
> real
> case, for example, is described here:
> https://sourceforge.net/p/courier/mailman/message/16554252/
>
> An MTA may want to offer this capability as a feature.
>
> A receiver only needs to check that the envelope value(s) are /included/
> in the
> signed rt=.  It is not much more difficult than comparing single values.
>
> The only drawback, AFAICS, is that when a message with multiple recipients
> is
> forwarded by a non-DKIM2 agent, or replayed, the final recipient cannot
> determine which one of the signed recipients is the culprit.
>
>
> Best
> Ale
> --
>
>
>
>
>
>
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