Undocumented Latinx youth in Tennessee envision higher education as the single pathway to enable their upward economic and social mobility. Many of these young people enroll in private, historically white, Evangelical Christian colleges that provide financial support otherwise unavailable to undocumented youth. At the same time, university actors struggle to meet students’ other needs as undocumented and minoritized individuals. Based on long-term ethnographic fieldwork, I demonstrate how youth struggle with the hidden personal costs of educational access and the upward mobility it promises. Most significantly, Latinx immigrant youth must navigate the tensions between the ever-present legacy of racial segregation and animus in Evangelical traditions and their status as the embodiment of newfound, institutionally desirable “diversity.” As these students negotiate deeply racialized social and academic orders, they grow ambivalent about the promises of educational mobility, particularly if that mobility is contingent upon conforming to “respectable” forms of diversity. Centering youth’s ambivalence reveals both the contingent value of educational mobility to those experiencing it and the limits of university policies intended to increase educational access.