Hello, I followed the instructions of David Woodhouse and built openconnect 5.99 for windows (tried 32 and 64 bit versions) inside my fedora vm: http://lists.infradead.org/pipermail/openconnect-devel/2014-March/001728.html I also installed the latest OpenVPN 2.3.4 (x86_64-w64-mingw32) and got the TAP-Windows driver version 9.9 installed too. Connecting with openconnect to my firm's cisco vpn server was easy, since the authentication is based on login and password only. I modified the vpnc-script-win.js to run only the following lines on "connect": run("netsh interface ip set interface \"" + env("TUNDEV") + "\" metric=1"); run("netsh interface ip set address \"" + env("TUNDEV") + "\" static " + env("INTERNAL_IP4_ADDRESS") + " 255.255.255.255"); if (!waitForInterface()) { echo("Interface does not seem to be up."); } run("route add 192.168.50.0 mask 255.255.255.0 " + env("INTERNAL_IP4_ADDRESS")); Everything seems quite straight forward and easy but I couldn't ping the internal network 192.168.50.0 even though the route seems to be added. I made sure to run openconnect as administrator and made sure the tap interface was configured properly. If I connect with the cisco anyconnect client it automatically sets the INTERNAL_IP4_ADDRESS + 2 as standard gateway and routes all my traffic through the vpn tunnel. I also tried to setup a configuration like that but it didn't help either. The tap driver is installed properly since I'm also using OpenVPN on the same windows 8.1 machine to connect to another vpn server. To verify that openconnect is capable of connecting to my firm's cisco vpn server I tried it under my fedora vm and it worked properly. I'm out of ideas on what might be the cause for the tap driver/routing not working. I also tried the openconnect --dump-http-traffic option and noticed that pinging a host within the 192.168.50.0/24 network wouldn't cause any extra traffic. Couldn't it be something wrong with the interface between the tap driver and openconnect on windows 8.1? Cheers