Somewhat related: https://www.eff.org/deeplinks/2016/12/https-deployment-growing-leaps-and-bounds-2016-review https://www.eff.org/deeplinks/2016/12/https-deploy

Somewhat related: https://www.eff.org/deeplinks/2016/12/https-deployment-growing-leaps-and-bounds-2016-review https://www.eff.org/deeplinks/2016/12/https-deployment-growi... (my post on HTTPS deployment improvements during 2016, a whole lot of which involved Let's Encrypt)