This study explores the organizational challenges encountered by afternoon school leaders in the North and South Al Batinah Governorates of the Sultanate of Oman, specifically within the context of the double-shift system employed to manage high student density and optimize infrastructure. Utilizing a descriptive qualitative methodology, the research gathered data through semi-structured interviews with a purposive sample of six female afternoon school principals. The data were processed using thematic analysis and supported by ATLAS.ti software to identify recurring patterns in professional administrative experiences. The findings indicate that these challenges are systemic and interconnected, characterized primarily by shared facility limitations, severe time constraints affecting administrative efficiency, and a breakdown in organizational communication between morning and afternoon shifts. Furthermore, the study identified significant human resource shortages and obstacles in parental engagement linked to the afternoon schedule. Consequently, the study recommends enhancing administrative coordination, expanding the decision-making authority of school leaders, and transitioning toward blended learning models. It ultimately underscores the necessity of providing independent facilities for afternoon schools and calls for further research to refine organizational models for multi-shift educational systems............... Keywords: .....Organizational Challenges, School Leadership, Afternoon Schools, Double-shift System, Educational Administration, Oman.