Re:Encryption and ease of use. (Score 1)

I haven't entirely thought this idea through, but I'm not aware of anyone having attempted such a thing.

Hmm, well, I've been in touch with a company in the Netherlands, http://www.nedsecure.nl/ who offer pretty much what you're suggesting.

Transparant email encryption through a webserver/webmailportal. So you can send encrypted messages to your clients, they get a notification mail, and can check the mail you sent online. Bit cumbersome perhaps, but well, technology probably improved from back in nov-2005 that I saw these guys at some InfoSecurity convention.

Unfortunately, the site seems to be dutch only, but dutch ain't too different from english, with some imagination ;)