This article examines educator participation in training initiatives based on Brazilian federal education legislation (Law 10,639 from 2003) in one city in the state of São Paulo. Law 10,639/03 represents a significant moment in the institutionalization of ethno-racial policies in Brazil over the past 15 years. It makes obligatory the teaching of African and Black Brazilian history and culture in all school subjects, and requires in-depth study of black contributions in the social, economic, and political spheres. The article first contextualizes understandings of race and racism in Brazil, followed by an elaboration of the political and epistemological underpinnings of ethno-racial educational reforms focused on Afro-descendants. The article then analyzes the contradictory processes that emerge from teacher training initiatives where the perspectives of anti-racism, multiculturalism ("pluriculturalismo"), racial democracy, and miscegenation intermingle and get reconfigured into understandings that have the potential to advance as well as impede critical engagement with racism and racial inequality. Rather than view teacher training initiatives as default decolonization or inevitable co-optation, this article outlines a more complex and contradictory account of state-society collaborations on educational initiatives. The article reveals the practical challenges of decolonization to argue that anti-racist activism in the educational sphere must take seriously the variable and contingent results of such political efforts in order to meet teachers where they are at while also challenging them to go beyond these limitations.