How To Enable Mom w/ Encrypted E-Mail?

mad.frog asks: "Given the recent revelations of the Bush administration spying on US citizens without warrants -- and their promise to continue doing so -- it's clearly high time for me to switch to encrypted email, after years of being too lazy to bother. The real question is how I can get all (or at least some) of my email contacts to switch as well; clearly, encryption does me no good if the recipient can't decode it. What are my options, and more importantly, what are the options that will be comprehensible and usable by my parents, and in-laws? (Keep in mind that good solutions must include robust Windows and Mac support...)"

Comments

I hope you know

[missing000]

Encrypting your communications like this will just cause you to be a target. The NSA can most likely crack whatever you can throw at them, and even if not they will not hesitate to use some more creative methods if they want to listen in.

Personally, I just assume that whatever I write or say is being listened to. It sucks, but that's the world we live in. Don't like it? Vote for a non-fascist next time.

GMAIL and Thunderbird/Enigmail

[Dark Coder]

To send email securely over your Google's gmail account, just configure Thunderbird mail account to retrieve gmail email using your Google POP3 account information.

Thunderbird/Enigmail combo neatly address your privacy issues for both sending and receiving.

With PGP/GnuPG perfect forward-secrecy protection, you can leave all your emails in your gmail account and not bother to delete them (EVER or until your GnuPG passphrase is compromised).

Google deux-machination of trying to find AdWords in your email for their massive onslaught of advertisement campaign will come to a screeching halt when your gmail InBox contains nothing but psuedo-random data.

Good riddance to invasive AdWords into your emails...