Introducing first-year college students to complex thinking is often complicated by their reliance on external authority. A key task for educators is identifying the nature of experiences that offer academic challenge yet are accompanied with sufficient support for students to engage these challenges meaningfully. The authors report the nature of the academic challenge that participants in the Wabash National Study viewed as important to their learning in their first college year. These include engaging in deep analysis, exploring multiple perspectives, and using perspective taking to refine their views. (Contains 2 footnotes.)