It is generally easier to use Squid in reverse mode. It is a production quality proxy that can do reverse proxying. You can generate a CA cert, install it onto

It is generally easier to use Squid in reverse mode. It is a production quality proxy that can do reverse proxying. You can generate a CA cert, install it onto Squid chain it to privoxy and install the CA cert into your browsers. Mitmproxy is great and we use it a lot, but it will have a pretty big hit on your performance. They have a more streamlined tool, mitmdump that is more aimed for these use cases, but it is still not written for performance first. https://www.cyberciti.biz/tips/linux-setup-transparent-proxy-squid-howto.html https://www.cyberciti.biz/tips/linux-setup-transparent-proxy... https://wiki.squid-cache.org/Features/DynamicSslCert https://wiki.squid-cache.org/Features/DynamicSslCert https://wiki.squid-cache.org/Features/SslPeekAndSplice https://wiki.squid-cache.org/Features/SslPeekAndSplice That link is an exact recipe for what I am talking about. It isn't really trivial to setup, but it does work well. Then, you can transparently privoxy ALL of your connections. You have to mix and grind several ingredients together. Specifying proxy is always easier/better, but transparent with upstream (from squid) proxies is possible. Squid can also do much of the ad blocking as well like privoxy, just without as nice of a config look and feel. edit: Just keeping things simple, I use squid with dynamic ssl certs, non transparently and have most of the rules I used in Privoxy working fine on Squid as the "one proxy" to run browser through. This prevents needing to monkey with proxy rules. As a bonus idea I also run this Squid on a perma-privacy-VPNd box, and always force certain site traffic through using a browser configuration like ProxySwitch Sharp. If you are really paranoid you can keep your sensitive traffic through your home / more trusted connection (whitelist style) and then route everything else through Squid/Privoxy. Setting up a nice little Linux VM that simply can't route traffic without the VPN connection is very nice, it ensures traffic thru your little VM can't leak if something on the VPN fails.