It's possible to use openPGP + Mixminion. Than the content is save and it's only possible to see that a mail is sent to a Mixminion server, but not who will be the recipient at the end of the chain. Often Mixminon fails. There is TorK available for Lenny, but it comes without Mixminion, so I guess it won't be easy to compile it for Lenny. I was using Mixminion with Suse 10.x with and without TorK, but often it fails or it takes days, until mails will reach the recipients. The actual stable Suse is 11.0 and 11.1 is on it's way. For paranoid people Suse is the better distro. They also have AppAmor to protect applications to be hacked. I guess this is overkill, but I don't trust Google. I need to use Google and sometimes I'm doing this without using CustomizeGoogle.
You know CustomizeGoogle? http://www.customizegoogle.com/
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