There is a growing literature that has documented diminishing health returns on upward social mobility among Black Americans. Due to historical policies and practices, upward social mobility is often an arduous, isolating process for Black Americans, especially as they navigate predominately white educational and workplace settings. This paper advances the literature in several meaningful and innovative ways. The goal of this paper is to provide a qualitative account of the health costs of upward social mobility and describe how these costs could diminish health returns despite greater levels of socioeconomic resources. Focus groups and surveys were the data collection methods for the study. Inclusion criteria for the study were that respondents identified as African American or Black, were 24 years or older and had completed college. The total sample was 32 college-educated Black men (n = 12) and women (n = 20). The mean age for men was 39 (range = 26–50) and 33 years of age (range = 24–59) for women. Key findings highlighted in this paper include (1) hypervisibility and subsequent vigilance; (2) uplift stress; and (3) health costs associated with social mobility. The sum of these stressors is posited to affect multiple health outcomes and elucidate the mechanisms through which socioeconomic returns on health are diminished.