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This meta-synthesis examines 27 case studies from the International Successful School Principalship Project (ISSPP) across 11 countries to explore how successful principalship practices (SPPs) adapt to diverse contexts over time. Framed through Bronfenbrenner’s Ecological Systems Theory, the study finds that exosystem factors, such as local policies and accountability pressures, exert the most influence on principals’ actions, while principals in centralized and decentralized systems exhibit distinct yet adaptive leadership strategies. The analysis reveals that successful principals actively negotiate contextual constraints without compromising core values. Findings highlight the dynamic interplay of environmental systems over time and underscore the need for contextually grounded, community-engaged leadership to achieve equity and sustainability in school improvement.