1. A non-transitory computer-readable medium embodying a program executable in a computing device, the program comprising: logic that generates at least one intent grouping associated with at least one historical path followed by a plurality of users by comparing statistical measures of the at least one historical path, the at least one historical path comprising content request information and information associated with a topology of a site; logic that tracks a path followed by a user, the path corresponding to at least one of a collection of content requests and being associated with the topology of the site; logic that identifies a starting point associated with the path; logic that identifies at least one subsequent step associated with the at least one intent grouping; logic that determines whether a subsequent step associated with the path deviates from the at least one subsequent step, the subsequent step being at least one of: following a hyperlink, visiting a product detail page, or completing a purchasing checkout workflow; logic that, in response to determining that the subsequent step associated with the path deviates from the at least one subsequent step, identifies the path as associated with an unexpected behavior; and logic that generates at least one of a remedial measure and a preventative measure in response to the unexpected behavior wherein the at least one of the remedial measure and the preventative measure is at least one of raising a fraud risk measure associated with a user corresponding to the path, diverting subsequent content requests associated with the path to at least one alternative computing device, and initiating additional monitoring of the path.