Comment Most people just don't care (Score 1) 601
In 10 years as a software developer, I've had an almost countless number of passwords, credit card numbers, highly sensitive documents, and more sent to me via unencrypted email. Almost on a daily basis.
No matter how hard I try, people just won't use encryption. I managed to convince everyone in the office to use S/MIME, but this lasted about a week before people decided it was too much work.
It's not like they don't understand the risks so much as there doesn't seem to be any 'easy' turnkey systems out there that are cheap or free. S/MIME is included in all major email clients, but it's a pain in the arse to setup - I ended up having to do it for everyone myself.
Personally I think email clients should automatically (without user intervention) generate an s/mime key and sign all outgoing mail, and encrypt all outgoing mail where a signature is known. This way you'd end up encrypting all email without even realizing it. (Of course you'd still require user intervention to copy private keys between your different computers......)