This study reports on the challenges facing multigrade principals. Principals are regarded as curriculum leaders and have critical roles to play in the success of the school. However, school principals experience a myriad of complex challenges in the execution of their roles and responsibilities. The purpose of this qualitative study was to outline the findings from a small-scale, exploratory study. Five multigrade school principals participated in the analysis. Using an interpretative qualitative research approach, a multiple case study of five multigrade teaching principals was employed. Four or more years of teaching and leadership experience in multigrade schools were used as the criteria for inclusion in the study. Semi-structured interviews were used to collect data and thematic analysis was used to analyze the data. The findings showed that multigrade principals have workload issues and lack of professional development in leadership in multigrade contexts as some of the challenges facing them. In addition, participants cited managing the interface between work and home as another worrisome issue in their roles as principals. This study recommends that multigrade principals need to be capacitated so that they have the necessary competencies and skills to function effectively in their multigrade context. To enhance effective practices and policies in rural multigrade schools, policymakers need to comprehend the unique challenges that multigrade teaching principals face and radically rethink the principals' preparation programs to include multigrade teaching principals.