I have recently come to the conclusion that e-mail is fundamentally unsecurable. The things we want out of e-mail, and an e-mail system, are not readily compatible with encryption.
November 12, 2015
Testing the Usability of PGP Encryption Tools
[Interesting observation. I tried to do encrypted email with some other people for a while and it didn’t last long. Things like searching for an old email was impossible. And the subject of the email was never encrypted so you would either leak a lot of information with the subject or you could decrypt just the one email you wanted to look at again.—Joe]