For those of us needing to send secure/encrypted email periodically or frequently here's a service that really takes care of it:
http://www.sendinc.com/
This service only requires you (the sender) and the recipient(s) to each have an account with sendinc. The email is created on their site and sent with an encryption key to the recipient.
Read the information from this link if you think you might be a candidate...it even includes an 'add-on' for Outlook so you can create encrypted emails without logging into their site:
http://www.sendinc.com/about/how-it-works
