A system for generating a second factor authorization for a request to access a web site includes a data store having a computer readable medium storing a program for generating the second factor authorization, and a processor. A packet receiving unit receives the request from a user device via a local network to access the web site via an external network. A trigger database stores the web site. A device database stores a rule associated with the user device for the web site, and a corresponding paired device with the user device. A second factor determination unit requests a second factor authorization from the corresponding paired device in response to the packet receiving unit receiving the request. A communication unit communicates the request to the external network in response to a valid assertion from the paired device based on the second factor authorization.