Encrypted email is still a pain
The main challenge for me seems to be that users do not have a concept of maintaining a digital identity and the key management that goes along with it. They just expect their real world identity to somehow translate automatically.<p>This just does not happen. Though I wonder if government-issued digital ID might be of benefit here to encourage good practices. Estonian ID-cards carry key pairs, so if email clients supported GPG email with smartcard-hosted keys (uhh maybe some do but I never heard of one) then this might be an approach worth undertaking.