The only way to get people to encrypt their email will be to make them want to encrypt their email enough to overcome whatever hassle it takes to do so. Most p

The only way to get people to encrypt their email will be to make them want to encrypt their email enough to overcome whatever hassle it takes to do so. Most people seem focused on making the second part of that equation (the hassle) small. Which is great. But even if you can somehow get it to 0, that may not be enough to get it over the hill. That leaves making people want to encrypt their email. And abstract notions like the NSA aren't going to be enough. It needs to be personal and immediate. So: if you really want to encourage secure email, start intercepting clear email and responding to it. The surprise introduction of a third party in the email conversation will cause most people to realize their email is not secure (which almost everyone doesn't know) and create an impetus for action. Now, this is a pretty nefarious scheme (grey-hat at best) and extremely dangerous due to the inevitable legal freak-out, and I'm not going to be doing it, but if I wanted to encourage the world to move to secure email, it's how I'd do it.