This paper criticizes the checklist model approach (authority, accuracy, objectivity, currency, coverage) to teaching undergraduates how to evaluate Web sites. The checklist model rests on faulty assumptions about the nature of information available through the Web, mistaken beliefs about student evaluation skills, and an exaggerated sense of librarian expertise in evaluating information. The checklist model is difficult to implement in practice and encourages a mechanistic way of evaluating that is at odds with critical thinking. A contextual approach is offered as an alternative. A contextual approach uses three techniques: promoting peer- and editorially-reviewed resources, comparison, and corroboration. The contextual approach promotes library resources, teaches information literacy, and encourages reasoned judgments of information quality.