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An Op-Ed piece from ArsTechnica:
Every once in a while, a prominent member of the security community publishes an article about how horrible OpenPGP is. Matthew Green wrote one in 2014 and Moxie Marlinspike wrote one in 2015. The most recent was written by Filippo Valsorda, here on the pages of Ars Technica, which Matthew Green says "sums up the main reason I think PGP is so bad and dangerous."
In this article I want to respond to the points that Filippo raises. In short, Filippo is right about some of the details, but wrong about the big picture. For the record, I work on GnuPG, the most popular OpenPGP implementation.
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Op-Ed: Why I'm Not Giving Up on PGP
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HELP! Man trapped in a human body!
(Score: 1, Informative) by Anonymous Coward on Monday December 26 2016, @05:15PM
Outlook does S/MIME natively, with no plugin or addon. The iPad, iPhone, iPod even, and most other iDistractions all do S/MIME natively, probably because the DOD uses S/MIME extensively and likely requires it for procurement. If the DOD thinks it worth using and it's supported on every client under the sun (I use Alpine's built-in S/MIME support) except webmail offered by privacy-hostile advertising companies like Google, maybe S/MIME is the right answer.