A network switch is configured to automatically establish a connection to a WAN by determining which of a plurality of ports of the network switch is a current uplink port leading to the WAN. The switch attempts to establish connectivity to the WAN using a first set of port configurations as the current set of port configurations. Upon determining that the first set of port configurations does not allow the network switch to determine an uplink port, the network switch changes to a mode having a first security measure and also having a relaxed set of current port configurations. The network switch again attempts to establish connectivity to the WAN, and upon further failures to determine an uplink port leading to the WAN, the network switch may be configured to switch to other modes utilizing further relaxed port configurations and the same or additional security measures.