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Free Will and Punishment
I want to have to use it, because it's cool, and it satisfies some sort of OCD / neatness thing for me to have everything signed that I send. But if you really look at it, how often are there challenges to email that isn't signed? When is the last time you heard from a friend that they wish your message was signed?
Right, probably never. Same here. So I'm less interested in the technology than I wish I was. It just doesn't seem as necessary as it is cool.
To me it's best use is for software developers who are putting out releases to be consumed by the masses. At that point the signature becomes crucial rather than just a novelty--although even then I wonder how many people even check the signature for downloads.
This kind of rolls into the same thing with PKI. Many browsers (until recently) didn't do automatic CRL checks. Almost all users blindly click "accept" when they see a server certificate that's self-signed or signed by an untrusted authority. One could argue the old "user education" rhetoric, but the average person's expectation of security is grossly over-simplified when it comes to things like this to make it practical, IMO.