Social justice leadership has become a popular topic and catchphrase in the field of educational leadership. However, most scholarly and empirical contributions have ignored the inherent tensions, challenges and dilemmas associated with the practice of school leadership and the realities principals confront on a daily basis. This is partly because researchers have tended to ignore multiple facets of justice in their empirical investigations as well as how larger forces outside the school associated with historical, political, social and economic injustices marginalize students and communities. This article explores three cases of challenging school-community contexts that confound and partially subdue the efforts of well-intentioned principals. Each case highlights a dedicated principal committed to their school and community, and documents the significant progress made in addressing particular social justice issues, but also how they confronted justice dilemmas that they believed required them to prioritize certain social justice issues over others. These findings have important implications for how principals view their communities and engage in critical reflection about the leadership decisions and actions they take on a daily basis. This article concludes with implications for future research and a discussion of how aspiring principals can be better prepared to lead for social justice and effectively address justice dilemmas without ignoring or putting off other injustices.