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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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If bankers can count, how come they have eight windows and only four tellers?
(Score: 1) by cpghost on Tuesday December 27 2016, @03:20PM
Well, since Google needs to scan your mails to target advertisers, PGP integration into GMail won't happen, at least not on the free GMail accounts. But maybe they'll be willing to integrate that on their Gmail-for-Work paid services.
And even if they integrated PGP into GMail, there's still the issue of key management. In other words: where do you store the private key? If you keep it on your computer, you'll need to sync it to your mobile devices, it can get lost, etc. If you upload it to Google's servers and attach it to your Google Account so it is always available, then even if protected by a passphrase, that kinds of defeats the purpose of a private key, doesn't it?
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(Score: 2) by urza9814 on Wednesday December 28 2016, @05:40PM
Well, if you're using PGP on Gmail, you've really got to trust Google anyway, so you might as well just give them the key.
The OP suggested giving Google your public key, then having them sign/encrypt for you. But that means you give Google the plaintext contents of every message. Even if they encrypt locally in Javascript, unless you're checking the code every time there's no guarantee they haven't added Javascript to pull the plaintext as well. I don't really understand how there's any benefit in not giving them the private key if you're giving them the ability to read all of your mail anyway...
So, there's two options. You encrypt locally, then copy/paste into Google. Which means there is no "Gmail integration" problem, because there can be no integration. The alternative is you give Google both the public and private keys and trust that Google will keep it secure and that your SSL connection is safe. Might as well let them generate the keys in the first place, since I don't see the average user being willing to do that.