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Comment by tptacek | Hacker News Reader

All of this of course skates past the problem that PGP's UX practically guarantees that someone will eventually reply to an encrypted email in plaintext, often compromising the whole conversation. Practically everyone who has used encrypted email "at scale" has seen it happen. An intolerable, irrevocable disaster we accept only because most of us don't actually care about the cryptographic security of our emails, most of the time.

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Autocrypt is a sensible approach leveraging PGP but avoiding most of that ceremonial UX. Unfortunately the gnupg project is heading in its own direction with major clients such as Thunderbird and Protonmail following. Few clients actually implement Autocrypt.

The group that has used PGP largely seems to like the ceremony required and chooses not to understand it is an impediment for both pervasive encrypted email and usability for nontechnical users. Hell even for technical users PGP is a hassle.

I'm doing what I can to spread the word on Autocrypt, but nontech types can't or won't switch to the few clients implementing it and the PGP fanbase sees their 6 levels of trust as Zimmerman given dogma that must not be altered under pressure of earthly realities, or security insights developed after the Code was written down.

>...the PGP fanbase sees their 6 levels of trust as Zimmerman dogma that must not be altered under pressure of earthly realities, or security insights developed after the Code was written down.

I am an actual OpenPGP shill who is entirely in favour of a very conservative approach to the standard but I really don't see the problem here. Autocrypt is a separate standard. Clients can implement it completely and just switch the trust to OpenPGP if a PGP identity shows up. There is nothing wrong with a client adding some extra trust information to accommodate autocrypt.

Autocrypt requires its own separate PGP contacts database (regular PGP standard doesn't allow automatic key overwrites), and as such most MUAs prefer to limit the number of things they support to old PGP. This is a problem for adoption.

PGP has the best UX for its purpose: a social graph tool for nerds.

I had a bug opened against evolution for something like a decade because it defaulted to using plaintext in replies to S/MIME encrypted emails. So it's far from only a PGP UX thing.

I'm still not sure they've fixed it... I haven't checked for several years now.

IIRC Outlook did the right thing by replying in ciphertext, but it also did the unhelpful thing of attaching the plaintext in a separate MIME part

Even systems that try to improve upon the UX and simplify the process, like Entrust, still suffer from this problem.

PGP seemed almost like magic when I first used it, but I look forward to it being relegated to the history books.

I think PGP has played an important part in propagating encrypted communication, and I think it's still quite useful as a tool for teaching/learning about asymmetric encryption, but there's just way too much friction for practical use for most people.

I wonder if there's some sort of educational tool/walkthrough that uses PGP under the hood but explains each step as you go...

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