A system and method of accessing web or network sites interfacing through a walled garden web server by dynamically expanding the reach of the walled garden on a user-by-user basis, based on the content that is returned to the user. The system includes a traffic analyzer and filter, a traffic forwarder, a traffic tagger, and a traffic redirector. A plurality of databases interface with the traffic analyzer and filter for appropriately manipulating web traffic from users by matching URL requests from a user with seed URLs in one or more of the databases. A depth parameter may be associated with a URL, indicating the number of times a particular domain has been traversed by a particular user. A depth rating database may be used to specify the number of times a particular URL may be accessed.