Participating:

On Wed, Mar 26, 2025 at 3:04 AM Alessandro Vesely <ves...@tana.it> wrote:

> >> In this strawman, the "rt=" single recipient construct is meant to
> support
> >> Bcc and other privacy sensitive cases where it only makes sense to have
> a
> >> single recipient.  Declaring multiple recipients that are not privacy
> >> sensitive is done through RFC5322 address headers.  As you point out,
> it's
> >> easy to extend it to also support multiple recipients.  The advantage
> of
> >> the approach you propose is that the signed recipient list is
> conveniently
> >> in the DKIM2-Signature "rt=" and can better represent the recipients
> that
> >> will be in the SMTP envelope.   The advantage of the approach of using
> the
> >> RFC5322 address headers is that they are already there without
> duplication
> >> of the addresses.
> >
> > Two other considerations.
> >
> > First a way to view the pros and cons for single vs multiple recipients
> is
> > the implementation tradeoff.  Single recipients will require additional
> > message splitting by recipients.  Multiple recipients will require
> signing
> > and verifying envelope recipients in the message header somewhere, be it
> in
> > the "rt=" or in the RFC5322 address headers.  Which of these is easier
> to
> > adopt by open source DKIM and SMTP packages?  Might splitting all
> > recipients be a simple config already in those open source SMTP?
> >
> > Second is a smaller worry about the effects of a long DKIM2-Signature
> > header.  If the "rt=" lists all envelope recipients, what is the effect
> of
> > the maximum number of recipients possible e.g. Gmail supports
> > <https://support.google.com/a/answer/166852?hl=en> up to 2000
> recipients.
> > I would imagine this reduces readability.
>
> Looks good. It's very elegant because by making rt= optional, it
> minimizes the surface differences with DKIM1.
>
> However, I'd still allow multiple rt= recipients, in case forwarders
> resend messages to multiple recipients at a time.  AFAIK, most or all
> mailing lists send single messages, otherwise they couldn't do VERP, but
> I'm not sure it's a universal rule.


One of the drafts I wrote about this previously proposed including all of
the recipients in the hashed content fed to signing without adding them as
a tag.  That still binds the signature to a specific set of (one or more)
recipient(s) without making them visible, possibly revealing a private Bcc,
although as Jim correctly pointed out, you can still do brute force attacks
to figure out to whom the message was addressed.

-MSK
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