Race and class differences in academic and social integration matter for educational success, social mobility, and personal well-being. In this article, I use interview data with students attending predominantly white four-year research universities to investigate the integration experiences of black and first-generation white men. I examine each group's accounts of both high school and college. Both groups of men reported having positive social experiences in high school. However, while first-generation white men were able to transport their identity strategies to college, the transition to college complicated integration and identities for black men. These processes supported white men's collegiate goals but undermined black men's, increasing the emotional costs of college for black men, undermining academic support, and blocking their ability to construct satisfying pathways to adulthood. I argue that identity experiences in high school matter for identity processes in college, where contextual intersectional identity expectations can change in unexpected ways for different groups. More attention is needed to the relationship between precollegiate and collegiate identities and to the ways intersectionality complicates identity processes.