This paper explores the challenges and dilemmas of conducting ethnographic race research in the context of the South African situation, forming part of my ethnographic race research PhD project, conducted in two historically white, single-sex schools in South Africa. First, it critically examines the theoretical dilemmas on crucial issues of objectivity and subjectivity in conducting ethnographic race research. It then explores the role of gatekeepers in determining who does research in predominantly white educational institutions; and shares the challenging accounts on what it was like to break the invisible barriers of difference in order to build social relationships for the purpose of research in very antagonistic environments. Finally, the paper provides some brief critical reflections. Pseudonyms are used for all the respondents, together with the official South African classification system, which refers to Africans as people of African descent and to whites as people of European descent.