You are getting into dangerous territory if you want to MITM so many HTTPS connections. (You can do anything with HTTP you want. Starting with DNS blackholing i

You are getting into dangerous territory if you want to MITM so many HTTPS connections. (You can do anything with HTTP you want. Starting with DNS blackholing is best) Note that the software GP linked to doesn't (can't) strip ads off an HTTPS connection[1]. It can only completely block it. So for ads + content from a single origin, you can't do anything. If you really want get into individual HTTPS connections, you'd have to install a root cert into every single once of the computers and MITM them by presenting your cert. This is only done in scenarios where one has to control everything the client machines do. Otherwise you're (much) better off preinstalling uBlock Origin on all the computers. BlueCoat is a company which works in this space[2] (it acquired by Symantec last year). Even then, you risk breaking something sometime[3] [1]: https://www.privoxy.org/faq/misc.html#SSL https://www.privoxy.org/faq/misc.html#SSL [2]: https://www.bluecoat.com/support-services https://www.bluecoat.com/support-services [3]: https://news.ycombinator.com/item?id=13750379 https://news.ycombinator.com/item?id=13750379