This is a tragedy. We need to reboot email. Encrypt everything, including metadata -- given current hardware, the client can easily bruteforce it from a list of known keys. Build some sort of easy key distribution tool (connecting via p2p, dns, whatever, just build a goddamn UI). Ask existing transports to relax their restrictions enough to let fully-encrypted mail through, and build some intelligent webmail interfac…
I think we need to go one step further than encryption. We need to encrypt all communications expensively . Make algorithms which can be tuned to be arbitrarily expensive, computation-wise. Tune them so that it takes as much time as we can bear to encrypt and decrypt an email. Seconds, ideally. The goal is to make it so that some large fraction of our computational resources are taken up encrypting and decrypting com…
There's only one successful way to fight this: change the culture and change the politics.
Technical approaches are fine for shielding you today. At the rate the police state is accelerating, it's very unlikely to shield you tomorrow, as they're going to outlaw the means of shielding. They will not allow an arms race, they'll use their legal powers to shut it down, and make you a criminal.