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The fear of missing the mark often shapes how honors students approach risk in the classroom and, consequently, how instructors build risk-taking exercises into their curriculums. This paper explores the concept of propositional risk in the context of honors pedagogy, wherein students are challenged to interrogate deeply held beliefs and tasked with exercises designed to call forth the full complexity of attendant issues surrounding any individual viewpoint. As distinct from strategic risk, which can be characterized as performative and externally motivated, propositional risk requires students to critically evaluate a spectrum of thought, value, and ideology in the context of singular, independent vantages. The author uses examples from a study abroad program and provides tips for fostering propositional tension in the classroom, suggesting that this type of risk, latent with the potential for change, is of greater benefit to the student long-term.