On Thu 20/Mar/2025 19:54:02 +0100 Allen Robinson wrote:
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.


A DKIM2 verifier can only verify consistency for recipients in the transaction in question. In the linked example, if all recipients are in the same company, addressing them all in a single transaction could make it possible for the receiver to verify that they were all properly addressed. A feature not (yet?) considered for DKIM2.


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.

Agreed. For non-DKIM2 receivers it doesn't matter.

Another argument for allowing multiple recipients is the consideration of what kind of hack a filter needs to employ to force a single-rcpt transaction. This is still necessary for Bcc:, although a special provision could be made for internal Bcc:s, such as Bcc: to themselves, which do not need verification. However, in some cases, the ability to use multiple recipients can actually simplify implementation.

Yet another point, purely psychological, is that a protocol that doesn't impose single-rcpt transactions will certainly be considered less disruptive to SMTP than one that does.


Best
Ale



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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