Two of the central missions of higher education are to foster the capacity to interact across differences and to cultivate a citizenry that has an appreciation for the diversity of ideas, perspectives, and cultures that exist within an increasingly complex and global society. Analyzing data from the Wabash National Study of Liberal Arts Education with hierarchical linear modeling, this study examined the effects of individual and institutional characteristics on first-year students' growth in openness to diversity and challenge (ODC). Consistent with previous studies, our results suggest that curricular and cocurricular diversity-relevant experiences were significantly associated with increases in students' Time 2 ODC. Institutional factors such as diversity density with respect to race/ethnicity and institutional type were found to moderate increases in Time 2 ODC, implying that the benefits of diversity-related experiences may be enhanced with the influence of a specific organizational context. These results can guide educators and administrators to foster educational environments and to utilize educational practices effective for promoting students' ODC. Moreover, our results reinforce the need for policies that promote and support the creation of structurally diverse campuses if students are to fully reap the educational benefits of their diversity-related experiences.