Focusing on the interplay between community context and principals' leadership, this study contributes knowledge of the situated dimensions of school leadership. Based on qualitative content analysis of the statements of 20 principals leading schools in low-socio-economic status communities in a highly segregated Swedish city, we address the research questions: (1) Which context-related characteristics of low-socio-economic status schools emerge, and what challenges do they entail? and (2) How do such characteristics and challenges affect and contribute to shaping the principals' leadership? The findings indicate four community-context characteristics, which also characterise or affect the schools' student and parent base and, in some respects, also the staff of the schools: high mobility, comprehensive linguistic and cultural diversity, comprehensive knowledge diversity, and extensive problem complexity. The analysis reveals that these characteristics entail work-related challenges with implications of both quantitative and qualitative nature, contributing to shaping a leadership that is present, gatekeeping, sheltering, collaborative, and compensatory and aimed at maintaining a resilient organisation. Considering the findings, the importance of recognising the particularities of context and the context-specific knowledge required is highlighted, as well as the potential value of tailored context-sensitive training and support for principals from local education administrations and universities.