I'm doing some usability testing of a web application and am attempting to debug and record some SSL sessions using mitmproxy as a transparent proxy and for some reason pf under Mac OS X Mountain Lion isn't setting up the transparent redirects. First, I enable forwarding: sudo sysctl -w net.inet.ip.forwarding=1 Next, I create a simple pf.conf file with a single line on it: rdr on {en1, en0} inet p