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Have them use Hush, or any number of the in-browser GPG/PGP extensions that will encrypt your gmail then! At least their webmail is encrypted then (and Hush integrates with most of the notable PKI servers). You have to start them somewhere, just lamenting about it isn't going to change anything. I've moved my family and friends into GPG over the lsat few years and now I receive GPG-encrypted mail more often than not.

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Browser plugins are good, but they do not solve the problem most people have complained about to me: that they cannot check their mail on their friend's computers, at the library, etc. Hushmail is snake oil, I would not recommend it to anyone and I doubt that it is even relevant to the problem at hand (how to communicate privately in a world of NSLs).

Use a USB key with everything installed on it in a portable fashion. The Tor Browser Bundle is something like this.

Two issues with this method are that TOR is 80% funded by the us government, using a computer opens you to backdoors.

But at least that's a good start.

You can also use Countermail which provides end-to-end PGP security (unlike Hushmail). Here's my article with more info: http://www.greycoder.com/how-to-stop-the-nsa-from-spying-on-...

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