* Why Johnny can't encrypt (1995): https://people.eecs.berkeley.edu/~tygar/papers/Why_Johnny_Ca...
* Why Johnny still can't encrypt (2006): https://cups.cs.cmu.edu/soups/2006/posters/sheng-poster_abst...
* Why Johnny still, still can't encrypt (2016): https://arxiv.org/pdf/1510.08555.pdf
At this point I really wonder if e-mail is the best solution for encrypted asynchronous communication. E2E systems like Signal or Whatsapp offer a very functional, intuitive way to protect your texts.