@hpk @delta @bascule @just1602 Yes, you can encrypt the From, but it breaks bounces and opens up a huge spam problem, and would be rejected by most SMTPd. You really want to protect delivery metadata from both the sending and receiving SMTPd servers. Assuming totally custom STMPd, you could have a key pair for each server, so that sender's client encrypts the "To" using the public key of the recipient's server, and the "From" using the public key of the sender's server. This could work fine, with minimal protocol changes (e.g. bounces work normally, server reputation and spam prevention work normally). Which leaves open the problem of two users on the same server. You would have to come up with some very un-SMTP system for this. Basically, what Signal does, and have per-recipient delivery tokens that let you deliver to an SMTPd unauthenticated, through open relays. Not impossible at all, just not really SMTP.