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This paper explores how U.S. principals navigate and mediate contemporary external tensions and influences to lead successful schools in diverse, underserved communities. Cases featured in this paper are derived from the new ISSPP theoretical framing with ecological systems theory and complexity theory, as well as new protocols designed to elicit how principals navigate and mediate multiple, complex tensions in their schools. The research design featured a purposive sampling strategy, semi-structured qualitative individual interviews, and qualitative coding in a comparative method. Findings introduce a new leadership domain that highlights the interplay between a successful principalship practices and the complex ecological systems in which they work. The article concludes with implications for future research, leadership preparation, and development.