Six Colors mentions that the GPG encryption author is running out of money. Now, like Dan Moren, I don’t have a whole lot of sympathy. That tool is a royal pain to install. I also think that Apple’s limited encryption (to and fro iCloud servers) is insufficient. What we want built into OSX/iOS is per file and per message encryption. Apple could write something like that and write a plugin or app for other services like Android. I think that’d make Apple a lot more attractive for many people and also drastically improve the state of mail on the internet.
Let’s be honest, mail started out as a trusted naive service largely within academic environments and never was designed for what it became. Yet changing the overall protocols hasn’t been successful. (Microsoft’s come closest with Outlook and Outlook server) Building something more secure on top of them is the way to go. GPG was a great idea with a poor implementation — largely due to the difficulty of putting it on most services. Having it ubiquitous requires someone like Apple stepping in.