The study sought to investigate the challenges confronting circuit supervisors in the Gomoa East district of Ghana. The study adopted mixed method approach of the sequential explanatory design. Interviews and questionnaires were used to gather data from fifty participants. The population included circuit supervisors, head teachers and teachers. The study used purposive sampling techniques to select 50 participants for the study. This comprised 5 circuit supervisors 20 head teachers and 25 teachers within the Gomoa municipality. The findings from the study showed that the challenges that confront circuit supervisors were lack educational resources and logistics, irregular in- service training, uncooperative attitudes of teachers and head teachers, poor remuneration, incentives and allowance and irregular visits to school. Strategies that were suggested to improve supervision were adequate funding and provision of materials and logistics, on the job professional training for educational field officers, supervision on regular basis, better remuneration, incentives and allowance for educational field workers and supervision on regular basis and effective collaboration between teachers and circuit supervisors. The study recommended effective supervision of circuit supervisors’ supervisory roles by district directors of education. Government should recruit highly qualified supervisors and ensure adequate provision of resources and logistics and increase remuneration, incentives and allowance for circuit supervisors. There should be regular, effective and efficient organization of in –service training for all circuit supervisors in the Gomoa East district of Ghana.