Since schools closed in March 2020, CRPE has tracked a sample of school districts and charter networks as they tried to reach students and provide instruction. This report looks more deeply into a smaller number of districts and charter management organizations (CMOs), hoping to understand why they took particular approaches to remote learning and how their experiences last spring affected their plans for the fall. We present a series of case studies based on our dives into big-city districts (Baltimore City Public Schools and Chicago Public Schools), a large inner suburb (Aurora Public Schools), a rural district (Roaring Fork School District), and two CMOs working in urban areas (Green Dot Public Schools and LEARN Charter Schools).