On 2026-09-11 15:19, Al Iverson via mailop wrote:
On Fri, Sep 11, 2026 at 2:10 PM Benoît Panizzon <[email protected]> wrote:

Well, now we can not tell her anymore which of the 8 microsoft
recipients reported her email.

Yes, I understood the problem as you described it.

+1
Coding around this issue also is not tivial

Nope, it is not. But it is not impossible.

and even desirable. In an ideal world, every participant ([email protected], [email protected]) would have a digital keypair, with the public key hosted somewhere at https://example.com/.well_known/email/user/key.pub and the private key either in safe custody of their service provider or, better, in their own possession, preferably on a hardware token.

in said ideal world, said message *could* be:
- of the highest standard: encrypted using the recipient's public key and signed using the sender's private key
- of the common standard: like today, plain text
- or in between (signed not encrypted; encrypted not singed)

in said ideal world, the sender would declare in some standardized header the nature of the email. text field (open ended) with some standard natures such as "personal" or "invoice", but also room for creativity and honesty ("account statement with embedded ad"). the recipient would be presented with a simple interface asking whether what they see correspond to the declared nature, and so the feedback would not be just wanted/unwanted; but rather honest/dishonest. because recipients make mistakes, and sometimes they have also bad days and just throw into the dustbin what on other days they would not.

in an even more advanced stage, participants could add policy statements in https://example.com/.well_known/email/user/policy.md. machine-readable policy statement will further inform service providers. for example, I as recipient could have a policy to require encrypted message, and with such a requirement, my mailbox provider will know to return undeliverable messages that are not.

yes, that means that email messages will become unique for each recipient, and that will increase network volume and computational requirements. arguably, it will lead to better quality, lower overall volume, and the resources will be used to generate more systemic value.

yes, that means non-trivial changes to the software along the chain. Benoît's server will have to make twenty different copies out of the one Granny message, verify each individual's recipient's key/policy; possibly compute encryption twenty times; and then apply Granny's signature twenty times using her key that is probably in the server's custody anyway.


I suppose the harder problem is to nudge your users to not send mass
email invites without using a tool better suited for that purpose.

the even harder one is to nudge them not to send emails contrary to the recipients' wishes.

Granny "mass" mails twenty recipients once a year.

I deal with "professional" organizations mass mailing tens of thousands of recipients once a day, enabled by Salesforce and its likes. Not picking specifically on Salesforce, it was just the tool used in the last obnoxious campaign fired at me by some idiot marketer.

best,
Yuv

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