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I've been very impressed with how Keybase has evolved, and how well they explain their model to users. It is without a doubt what I'd recommend to a semi- or un-technical user to get them started.
They have a walkthrough of their approach to security and threat models here: https://keybase.io/docs/server_security
And they explain "tracking" in detail here: https://keybase.io/docs/tracking
More than only create a great documentation, the wrapper they wrote in NodeJS abstracts GnuPG commands making easy to any un-technical person to use cryptography constantly. Of course a little bit of paranoya is always good, and I don't agree with the idea to host my private keys in a server I don't control, even cyphered with a password, but I think it can solve the problem that users forget or loose your keys and our keychain remains with unuseable, no revogated keys. CheerS - -- echo 920680245503158263821824753325972325831728150312428342077412537729420364909318736253880971145983128276953696631956862757408858710644955909208239222408534030331747172248238293509539472164571738870818862971439246497991147436431430964603600458631758354381402352368220521740203494788796697543569807851284795072334480481413675418412856581412376640379241258356436205061541557366641602992820546646995466P | dc -----BEGIN PGP SIGNATURE----- Version: GnuPG v1.4.14 (GNU/Linux) Comment: Using GnuPG with Thunderbird - http://www.enigmail.net/ iQEcBAEBCAAGBQJTqV9jAAoJEG7IGPwrPKWrSqUIAJvz47cjDQ5A3k7kOowbvinR i5+epHyDZYdYVAYmAlge9mLv4MnUDSsMYBFTtwKRuV8p5Afpr4SYsjFRZDOo0v3F kMZhPs7CPtigeWgXAlADHiO8V9+0PKv7r8StZARh5QtuZqh7P45+vEEjCi9hcdv3 QvmeTsAUVQrA+NZMvdr+iaCUFwI+RX/5fveJyoxFSIk0OBavkdL/NtYsIZhgtWwQ DrYrHSzTSkXsiFczNXtSysrIjypJ9zRt046sHi8haClQkDPi1JZejzG9OKAkFu5E O4bkZjjRZtb//tVQTj0MhCDcRhoWA50MNGVrUbe29UApFpT6fYbsKS+3bQ0GGYk= =xPvg -----END PGP SIGNATURE-----