A diverse and historically underserved urban student population struggles with academic learning and social adjustment in a context of limited resources. Support for staff efforts or special student needs is also limited, making it harder to attract and retain qualified staff. Given the conditions that educators must contend with in such settings, what does the attempt to improve teaching and learning imply for the work of leaders within schools, central office staff, and for others who contribute to the system of public education? One source of answers comes from a close look at schools and districts that are making progress, by varying local definitions that include measures of student learning. With support from The Wallace Foundation, the authors have conducted recent research that examines such schools and districts, and the findings of these studies substantially add to their insight into the urban educational leadership challenge. Leadership for learning improvement is hard work, as is the work of supporting this leadership, and it is made harder by dynamics and conditions that typify urban educational settings. The authors' analyses underscore several aspects of the effort to support leadership for learning improvement that will continue to challenge education leaders, especially under the conditions that prevail in many urban settings. In particular, participants at all levels face a steep learning curve, in part because changes in work practice are not minor incremental adjustments, but rather fundamental shifts in how teachers leaders, principals, and central office administrators do their daily work. Four themes capture central ideas across the three studies of leadership for learning improvement and the conditions that enable it. School and district leaders in these sites: (1) Focused persistently and publicly on equitable and powerful teaching, learning, and instructional improvement; (2) Invested in and expanded an instructional leadership cadre within and across schools through targeted investments, restructuring, and the reconfiguration of staff roles; (3) Actively reinvented leadership work practice, especially between school and district central office; and (4) Paid explicit, sustained attention to leadership support at all levels.