Why Johnny Can't Encrypt (1999 USENIX paper)
usenix.org
usenix.org
Incidentally I thought the article was going to be about why amateurs can't/shouldn't write encryption algorithms (having inquired about this myself on Stack Overflow and been royally shouted down).
But this messes up when you use the same terms for other uses of public/private keys such as authentication. Still, the terms could provide a better mental model for people new to it to understand.
I'd loved to hear the thoughts of the security gurus on HN about this...
Google/Microsoft/Yahoo posts a blog post containing the following: "PGP keys for all addresses can be found at https://keys.example.com/k/foo%27example.com . This is recorded in a TXT record in our DNS in the following easy to understand format.
We invite other mail providers to adopt this standard. We will periodically check your DNS records prior to sending mail and, if set up properly, transparently encrypt all mail sent to you."
Essentially, solve key exchange like HTTPS solves key exchange: the user never has to worry about it.
Roughly between 1/4 and 1/2 of them (worse in a couple cases) succeeded at a given task (send a key, encrypt an email, etc). Others failed completely, or took a long time to achieve it (~30 minutes in several tasks for a couple people), and some couldn't manage the essentials - even with feedback - by the end of the 90 minute trial.
Reasons given for the failures were primarily focused around workflow / UI design.
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Strikes me as accurate, probably better than many alternatives at the time, which is somewhat frightening. And, given my experiences getting signing / encrypting working in Mail.app, it's hardly improved in the past decade. Thunderbird makes it simpler, but not by much, and I don't recall being able to use multiple keys easily.
I know most people would be looking at the Thunderbird-Enigmail-GPG route, but I've found Firefox - FireGPG - GPG to be easier to use, install and more usefull. Actually the most difficult part with that setup is getting GPG to play with FireGPG, include GPG with Firefox and suddenly public key encryption is easy and available to the masses.