E-mail Encryption suggestions.

[Matridom]

I'm looking for some good suggestions on what software to use for e-mail encryption. My cousin is in a small medical practice and due to privacy laws, encryption is required. Here are some of the conditions the software will need to operate under;

The stronger the encryption, the better.

E-mail will be sent through the wild, so the less configuration "clients" will need to do the better.

These people are not tech savvy and there is no onsite IT person. It needs to be easy to use and fairly idiot proof in usage. Professionals will be available for installation and occasional support of software.

Windows environment (workgroup), i'll need to check to see if it's outlook or not. (i'm fairly sure that it's windows mail). If the software is a replacement for the e-mail client, that may be an advantage.

Added bonus:
The software can encrypt files on the system in addition to e-mail.
Tech support from vendor included in cost of software

[NooNoo]

this is a good overall view (http://netsecurity.about.com/cs/emailsecurity/a/aa051004.htm)

this one offers blackberry integration (http://www.entrust.com/email-encryption/index.htm)

Sophos just acquired this (http://www.sophos.com/products/enterprise/encryption/utimaco/)

[Stalemate]

Pretty Good Privacy (http://www.pgp.com/) is still around, and we have it deployed at a client site where the users are in the same category as yours. ;)