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Why don't you give GPGMail a try? It's a plug-in for Mail.app and if you want you can use an installer which brings with it, all the requirements needed for mail encryption.
This is my first post and I hope I am following satisfactory protocol by responding to this topic, rather than adding a new one.
I can't get this to work either. My first attempt, I thought I was all set, but when I received a friend's email for decryption, found that I could not do so. All GPG related functions, from Mail, were grayed out. In my attempt to work things, I got a bit in the weeds for my competence level.
I think I am back to the status I was at when I got my friend's email. I have my keys generated, imported his public key, and have the same set of circumstances. I cannot decrypt his mail and all GPG options, in Mail, are grayed out.
I'm not familiar with GPGMail, but if it's a Mail plugin, note that Apple has been making some changes to Mail lately that require developers to update their plugins. I'm sure this won't be happening at every software update into the future - otherwise, why even have a plugin architecture? However, for now, you need to look to the developer of GPGMail for an update.