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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