This report published by Vanderbilt University Peabody College of Education and Mathematica Policy Research presents the efforts of six large school districts (1) Baltimore City Public Schools, MD; (2) Broward County Public Schools, FL; (3) Cleveland Metropolitan School District, OH; (4) Des Moines Public Schools, IA; (5) Long Beach Unified School District, CA; and (6) Minneapolis Public Schools, MN–to reshape the principal supervisor role as part of a 4-year, Wallace Foundation-supported initiative. While the principal supervisor position is available in many school districts, it has not always focused on the academic and instructional work of schools. Instead, it often centers on administrative concerns. In the districts that were evaluated, principals reported feeling better guided and evaluated by their supervisors and determined their central offices had made at least some progress in adapting to changes in supervisors’ roles. However, challenges in supporting the reconceived job remained.