1. Use fax. Practically, it is more secure. Given a motivated intruder, it is no less secure than email. 2. Use password protected PDFs. Tell your lawyer frien

1. Use fax. Practically, it is more secure. Given a motivated intruder, it is no less secure than email. 2. Use password protected PDFs. Tell your lawyer friend to use the person's last name and/or DOB (or some equivalently easy to remember token) as the password. Pre-arrange the password over the phone--since it is based on their name it is easy to tell them what it is. The key here is to stop the vast majority of folks who might stumble across the email. Again, given a sufficiently motivated intruder, this is pointless, but still more secure than plain old email. 3. Use encrypted archives of the documents. The files can be encrypted with AES256 or an equivalently difficult cypher. Test the type of archive/encryption to ensure that Windows XP and above will be able to decrypt the file easily w/ the build in archive folders. This can avoid any potential compatibility problems with #2 from above. It might introduce new ones. Using a web drop service doesn't eliminate the need to protect the file. If you password protect the file then you need to share the password. If you password protect access to the file, you need to share the password. The link in an email is nearly equivalent to an attachment, so it doesn't really solve anything unless you have an easy way to share a secret with the receiver.