ABSTRACT How can we situate discrimination and the internalization of negative stereotypes in their contextual and structural determinants? To answer, I empirically examine linkages between structural inequalities, ethnic discrimination and the internalization of negative stereotypes. Data come from the UNDP, interrogating the lived experiences of Europe’s Roma population ( N = 4651), utilizing a multilevel framework. I show that the relationship between stratification and stereotype internalization is more nuanced at the population level than what has been illustrated so far in controlled experimental research settings. Both structural inequality and discrimination influence the internalization of negative stereotypes. Ethnic discrimination and the internalization of negative stereotypes closely parallel each other. The above phenomena are distinctly influenced by factors such as gender, group educational attainment levels, group-level gendered income distributions and country-level political and economic contexts. My results show that in highly unequal environments, factors that we often think of as protective – such as higher education – may carry unintended consequences when it comes to the internalization of negative stereotypes. My analysis serves as an important first step in tracing the contours of the simultaneous effects of individual and structural discrimination on the internalization of negative stereotypes.