I worked at a small 25 bed hospital, we implemented the Sophos email appliance. It was fantastic, the basic setup was incredibly easy to do.
When you send an encrypted email out the recipient gets an email asking them to register, they create a password and are then mailed a PDF protected with the password they set. That same password will encrypt all of the PDFs they receive until they don't receive one for a period of time that you choose, at which point they create a new password. An outlook add-in is available that will allow you to quickly and easily stamp an email to be encrypted.
It also functioned as our spam / virus filter and was fantastic at it. We never setup or configured the scanning of outbound emails to force encryption although that was an option.
Loved it 5/5 wish we had it at my current place of employment. After I put it in place and configured it, I almost never touched it again.