1. A method of monitoring usage of a mobile device, the method comprising: determining, with a processor, whether a device is communicatively coupled to a WiFi network, the WiFi network identified by a Service Set Identifier; identifying whether proxy settings are configured on the device in association with the WiFi network; transmitting registration information from the device to a registrar if the proxy settings are not configured, the registration information comprising a classification of the WiFi network and the Service Set Identifier; and configuring the proxy settings of the WiFi network based on instructions received from the registrar, the instructions to cause the device to transmit network communications using the proxy settings when communicatively coupled to the WiFi network.