School leadership, next to teacher quality, plays the largest role in improving the educational outcomes of students. As such, federal and state policies have sought to hold principals accountable for the academic success of their students. Given the renewed attention paid to school leaders and overall school improvement with the passage of the Every Student Succeeds Act (ESSA), this article examines how district and school capacity to apply for and allocate additional professional development funds provided by ESSA might vary according to school context. We utilize qualitative interview data and the literature pertaining to ESSA to interpret how the new federal education policy might affect the preparation and development of principals and how ESSA might expand the social and economic divide that exists between and within districts. We find that while flexibility and autonomy might be key components of ESSA, under-resourced districts and schools might not experience such flexibility and autonomy due to a lack of resources--both human and fiscal--and a lack of capacity. Thus, we find that vulnerable schools might continue to struggle to improve in the era of ESSA.