An automated tool for determining the server-side technology underlying a dynamic Web site acquires one or more root Internet addresses, identifies hyperlinks within a specified link depth of each root internet address, extracts a file extension from a file name associated with each identified hyperlink, designates one or more dominant file extensions based on an analysis of occurrence data, and maps at least one dominant file extension to its corresponding server-side technology. The automated tool may, among other purposes, be used to generate sales leads or to develop a suitable migration path for a dynamic Web site.