My brother is a Computer Fucking Genius and this is what he sent me in an email asking about encrypted emails...
ok, don't know jack about hush mail just so you know.
there are only a few products I would use to encrypt anything that I didn't want somebody to know about. One is mainly for your computer, the other people use to encrypt files, email them and opened on the other side with a public key, the last for net cruising/downloading.
PGP (pretty good privacy) for file transfers via email etc. Public keys to send stuff to you encrypted so only you can open it. This is the way to go imho.
TrueCrypt for your pc drives, hidden partitions in partitions, secret operating systems etc. This sucker is the shitz. I want to get this up on my system eventually, just don't have a compelling reason to do so now...
Tor can be used as a anonymizer for running on the net without reviling who and where you are. Example would be downloading torrents, wares, dark nets, viewing websites you don't wish to be associated with etc. Very slow though.
They are free and run on Macs. Just google the links..easy to find. Nobody won't break any of this unless they want to run a supercomputer brute force style against it for a long time...assuming you have a fantastic pass phrase. (not word)
I don't know of a program that would just make sure what you are sending is scrambled from your computer to the receiver...that's just a SSL...secure socket layer, same stuff that's used when you check your bank balance online. Pretty pointless as you just hack one email account or the other in the situation you wish to use it for. Bottom line, Either have 100% encryption or none. (a hole in a wall means the entire thing is useless no matter the size.) If you used all the programs above and encrypted any disks you have it's damn near bulletproof...until your in court and the judge puts you in a deep dark hole forever until you give up the keys....and it's happened