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Re:WordPress.com turns on HTTPS encryption for all websites by pfg on Friday April 08, 2016 @03:28PM (#11457215)
I'm not sure if WordPress is actually doing this, but they might be using something like camo[1] to transparently rewrite any http:// URLs to an image proxy running on SSL.

This gets harder to implement correctly depending on what kind of content you allow on your sites (i.e. does your CMS only permit sanitized HTML, or are users allowed to do basically anything?), so it's not a perfect solution for everyone, but it might work here.

[1]: https://github.com/atmos/camo

Re:WordPress.com turns on HTTPS encryption for all websites by barsxl on Saturday April 09, 2016 @03:22AM (#11460337)
Photon[0] does exactly this (and more!) and is free to use as part of Jetpack[1]

0. http://developer.wordpress.com/docs/photon/ 1. https://wordpress.org/plugins/jetpack/

Re:WordPress.com turns on HTTPS encryption for all websites by stock_toaster on Friday April 08, 2016 @07:48PM (#11459039)
And if node isn't your thing, there is a work-a-like[1] written in Go.

Disclosure: I am the author of go-camo.

[1]: https://github.com/cactus/go-camo