Comment Only where PKI is pervasive (Score 1) 601
on my work network, we've got an integrated PKI that makes it easy for people to exchange their public keys. If I'm sending someone a password or other sensitive information, I'll encrypt it against their keys there. If I'm just talking to someone (ie: not doing anything sensitive), encryption is off, signing is on. If I'm sending from my personal email, the only person I encrypt to is my work email.
I think the big reason that email encryption in general hasn't taken off is that it's a huge pain to exchange keys. Some keyserver attempts have been made, but frankly there's not been enough adoption in any circle I've seen to really call it a success. The only time this stuff seems to really work well is when there's a corporate directory and a mandate from management that says "you will get a pki certificate, and you will publish it on the global address list".