Former research shows that student bodies of higher education institutions have become more diverse over the past several decades, both at historically Black colleges and universities (HBCUs) and predominantly white institutions (PWIs). Sociological research explains how diversifying colleges and universities may seem like a good thing, but actually causes problems for minority students through microaggressions and unequal academic playing fields. Although research exists which analyzes the admission of students of color, there is a gap in the research which looks at retention. This research aims to better understand what conditions make students more or less likely to stop out of college with particular focus on race and financial need. The econometric results show that being Black and attending a school with an increasingly white student body is not statistically significant in leading to a student stopping out, but attending a school with a higher percentage of white students reduces the likelihood of a student stopping out. Further, factors of financial need, including students who borrow more money to pay for their education or have a higher level of unmet need, are more likely to stop out. A series of sociological case studies reveal that PWIs have much work to do in making campuses more diverse and inclusive. Microaggressions and acts of racism can lead to a disconnect between a Black student’s identity and the environment of their college campus. Yet, the institutional support structures of PWIs may be enough to maintain the retention of Black students.