Teaching students how to use PGP is the best evidence I can provide that we need a simpler solution for encrypted email.
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I was trying to solve this by making an easy to use PGP client for iOS but the biggest problem is without a plugin system for Mail, I was severely limited by how easy I could make it. I ended up scrapping the project in the end.
Is there anything wrong with the MacGPG plugin? I found it pretty easy to send encrypted email with that, literally just a toggle button.
The problem isn't the encrypting, the problem is the moving around of keys and key validation. I don't have any good ideas as to how we can fix that.