This paper reports findings from five US schools that were studied as part of the International Successful Principal Project (ISPP) - a project designed to identify the qualities, characteristics and competences of successful principals in different socio-economic circumstances in eight countries. The five US schools reported herein serve elementary students living in different communities confronting challenging circumstances. Using Leithwood and Riehl’s (2005) four core leadership characteristics for successful school improvement to guide the analysis, we found that the principals in these schools not only demonstrated an ability to set directions, help people, redesign the organization and manage the instructional program, they also displayed qualities and skills necessary to address the challenging environments in which their schools are situated. Specifically, they used externally imposed accountability standards to focus the efforts of their school communities on improving student achievement and then, using an ethic of personal and professional care and by distributing authority broadly, they persisted in raising public expectations about what was possible for teachers and learners. In several cases, their concerns and efforts also extended beyond the school’s professional community, as they sought to develop closer relationships with communities outside the school, such as business and civic groups. The findings from these cases have implications for the practice and preparation of principals. Recommendations include strengthening preparation by addressing the core skills for school success, especially as they pertain to high poverty and other challenging communities.