Students entering the business workforce today may well share some responsibility for developing, revising, or evaluating their company's Web site. They may lack the experience, however, to critique their employer's Web presence effectively. The purpose of developing Digital Discernment, an e-commerce Web site evaluation tool, was to prepare students for this work. The tool provides them with a listing of criteria with which to assess e-commerce sites, lets them evaluate pre-selected sites qualitatively and quantitatively, and allows them to compare their evaluations with their peers. In this article, we discuss and examine the effectiveness of this tool and consider the ways in which it can help students in their future business careers.