This study explores participant experiences at two contrasting high schools in a large, urban school district in crisis who implemented mandatory community-based learning (CBL) (e.g. community service, work-based internships) as a policy of reform. Rawls' theory of justice as fairness is used to examine capacity of the district formal policy to achieve fair equality of opportunity central to its democratic aims and purposes. Researchers found disparities in equity and access was associated with critical agencies exercised on the part of key school personnel (e.g. internship coordinator) who navigated and resisted contextual structural barriers (i.e. transportation limitations, employer inflexibility, neighborhood economic conditions, cultural and religious norms) differently. Findings suggest implications for U.S. urban school districts with formal policies of mandatory CBL including consideration of local context and exercise of critical agency at multiple district levels prior to implementation in order to build capacity for formal equality of opportunity.