Students face challenging texts and concepts across the disciplines in higher education, and many students lack the reading skills and strategies to make sense of them. The aim of the small study described in this article was to explore the benefits, if any, of the difficulty paper, a written formative assessment that asks students to explore their difficulties with challenging texts. An inductive analysis of student difficulty papers in a multidisciplinary “Great Works” course suggests that the paper encouraged students to address their confusion without dismissing it and helped students to model the processes of good reading. Findings also suggest that the assignment may be a useful tool to develop disciplinary habits of mind. The article concludes with an example of how educators might use the difficulty paper in science and mathematics courses.