I apologize for the repeated email... got sent before time. To finish on the example: LanUser1 makes an http request -> The HTTP request is processed on a BOX that acts as a gateway --> That same box has squid installed and filters the http request (Normal ACLs) --> Depending on the private IP of the user the request is channeled through a specific VPN. What would be the best way to accomplish all this? Anybody has done it before? If the LAN user does not make a http request it should go direct to the corresponding VPN interface bound on the same machine. Regards, Dimitri