[Endymail] Why S/MIME and OpenPGP ecosystems fall short

[Watson Ladd <[e-mail]>]

Dear all,
Let's compare a messaging system like TextSecure to the experience of
secure email messaging. A user downloads TextSecure, starts using it.
It has a familiar UI, and encrypts when it can without any explicit
user invocation. If they want to validate keys, they can do so easily:
there is one fingerprint and clear instructions on how to compare it.
The semantics are exactly what is expected.

Compare to what happens with GPG. Immediately the user is asked to
make important choices with no guidance. Key discover is separate
step. When sending messages, they have to choose several orders of
operations and ciphers, with the wrong choice having consequences. I
don't think any choices have the right semantics. A lot of this has
been ruled out of scope as UI issues, but I don't think so: I think
that solving these issues require removing many of the problems that
we expose to users. Certainly some plugins do a very good job of
fixing some of these headaches, but I don't think any of them are as
reliable as TextSecure.

It's clear to me that this isn't easily fixable by standards work
alone: much of the damage is baked in to the functioning of S/MIME and
PGP. What needs to happen is that we need to come up with good ideas
around key management that are actually deployable, and provide the
semantics people want.

Sincerely,
Watson Ladd