I have been playing with these for some time now; you need patients though, as they tend to slow you down a bit. Mind you my box is not what you would call state of the art. Messenger works well with Tor and Privoxy. I have not come across a method of Torifying outlook though. I would be interested if anyone knows a way to do that.Quote:
Tor and Privoxy sprang to mind immediately
Mind you outlook has its own ability to encrypt out going mail.