A system and method may handle the supervision of the connectivity of a virtual private network (VPN) of a mobile device that is configured to connect through a plurality of network interfaces. A server may configure the mobile device to send a request for data item. The server may track the response of the mobile device to the request. According to one embodiment, the VPN may not be connected through a preferred network interface, while such interface is available. In such case, the data item may be routed through the preferred network and therefore not received by the VPN server within a predetermined period of time. According to another embodiment, the server may identify an internal IP address of the data item. The server may be configured to determine the current network interface based on the internal IP address. The server may disconnect the VPN to permit the VPN to reconnect through the preferred network interface.