Matt Haughey describes the difficulties he encountered when trying to give himself the ability to encrypt email: It’s the user experience, stupid. Very early on in my internet life I started using PGP and, as Haughey does, I periodically revisit the subject and assess how far things have progressed. As he reports, however, things haven’t progressed very far.
My most recent foray into encryption and such occurred a few weeks ago when I downloaded and tried the free GPG system. I found that not only could I not use my old key pair (though I still know my old password) but I couldn’t easily find out why, nor could I figure out a way to address the issue. So now there is a public key out there in the wild – a key of long standing and signed by several other people – with my name on it but with totally out-of-date email addresses attached to it and nothing I can do about that.
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FYI : Design Principles and Patterns for Computer Systems That Are Simultaneously Secure and Usable