Hierarchical Monitoring and Quality Assurance in education are the major issues for the nations of the developing world. Consequently a spurt is seen in endeavors to promote quality in education through differed means and mechanism. School supervision is seen as an effective mechanism for quality assurance in the schools as is evident from the roles assigned to the supervising officers. However, the supervisory functions to be performed by the education officers are found to be impeded by several factors that should be redressed to make school supervision contributory to quality improvement endeavors. The present paper discusses the variegated roles of school supervisors to establish the complexity of their roles. Consequently, it presents a review of the major impediments that prevents school supervision from achieving its goal of enhancing school performance in Jangalmahal, West Bengal.