Research Approach: This cross case study describes the challenges that two principals working in one urban school district addressed while attempting to transform their school cultures to embrace an inclusion model. Analysis of interviews and observations in each school revealed the actions, values, and orientations of the individual leaders and the influences of conflicts and dilemmas that exist in social justice work. Findings: The article describes how two principals enacted social justice leadership by making decisions that addressed resistance and challenges to inclusion. Implications for administrator preparation, future research, and theory are presented.