In an era of increased attention to academic achievement gaps, expanding educational options has emerged as one approach to meeting the diverse learning needs of urban youth. This multiple-case study uses teacher interviews to investigate the role of extra-organizational factors (e.g., district- or state-level mandates) in shaping teachers' work in small public "specialty" schools. We find that teachers feel their work is enabled by smallness and autonomy but constrained by counterproductive policies. The ability of school personnel to obtain and leverage power shaped their success in navigating their institutional milieu. We close with implications for educational leaders and researchers.