Let me start by saying that I didn't know this standard existed until about 2 days ago.<p>S/MIME seems to be built into most major email software (?) and is surprisingly usable. Not quite as easy as "it just works" in popular messengers, but still good given the nature of email.<p>The most difficult part was getting a signed certificate. There's only 1 free provider left (apparently) and the payed one I've tried was a worse experience. This is a hindrance, but something that could be solved if usage was more wide spread in the first place. But how come it (seemingly) never got off the ground in the first place?
1. "In any group of people exchanging encrypted emails, someone will eventually manage to reply in plaintext, usually with a quoted copy of the entire chain of email attached. ... it’s an irrevocable disaster. ... the Internet email system ... cannot enforce encryption. "<p>2. "The email “envelope” that includes the sender, the recipient, and timestamps – is unencrypted and always will be. Court cases (and lists of arrest targets) have been won or lost on little more than this."<p>3. "One of the fundamental features of modern email is search, which is implemented by having the service provider keep a plaintext archive of email messages. ... In reality, any email I send is likely to be archived forever."<p><a href="https://latacora.micro.blog/2020/02/19/stop-using-encrypted.html" rel="nofollow">https://latacora.micro.blog/2020/02/19/stop-using-encrypted....</a>