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It seems to me that S/MIME has a better chance for wide adoption due to it being built in to many email clients (Mail on OS X/iOS at least.) However it's still up to the user to get a certificate, which is a barrier. But I'm curious what others think, as I haven't seen S/MIME brought up in the recent encrypted email threads.

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It's true, S/MIME would seem to be a more convenient method for wide adoption...

The problem with S/MIME is that it is strictly hierarchical. That already hasn't worked well for TLS.

The aim of email encryption is in a large part to prevent government-level parties from reading the emails. It doesn't really make sense to then go back to a system controlled by the very same parties.

OpenPGPs web-of-trust model seems more appropriate.

But both approaches share a significant number of problems, so...

Yeah. They're pretty much free too, from Comodo and Startcom. You can get one for ~$10 from Certum (what I use) and $30 from Globalsign.

It's handy too, as I can sign emails using my iPhone just by importing my p12.

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