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Research on principal leadership dilemmas is important to understand the work lives of school principals to provide implications for leadership development. While researchers have reported principal leadership dilemmas in different contexts and not conclusively agreed on a particular framework, there are commonalities as well as differences. Thus, exploring principal leadership dilemmas at a systemic level is needed. This study explores factors that influence principal leadership dilemmas and how leadership dilemmas reflect school organization and school principal. Then implications for leadership development were drawn. The study adopted a content analysis and a qualitative metasynthesis approach to provide in-depth and systematic understanding of principal leadership dilemmas.