This piece of work investigated the Role of the Inspectorate in the Educational System in Kenema District. A descriptive analytical survey design was used to carry out the study. All the senior personnel were involved in the sampling including twelve supervisors, one inspector, three organizers, two football coaches and the Deputy Director of Education in Kenema district. Questionnaires were used and interviews held as and when necessary. Findings of the study clearly identified the roles of the inspectorate in supervising Primary, Secondary, Technical, Vocational institutions and non-formal literacy centers. It also explains the inadequate capacity of the inspectorate personnel in terms of human, material, finance and time for supervision. Participant’s revealed some problems encountered during supervision exercises such as, - Long distance with limited or no mobility - Inadequate stationeries - Too many schools and other learning institutions to be covered by very few supervisors within a limited time. - No reimbursement of travelling claims and overnight allowances - Unavailability of proper school records. - Negative attitudes of some teachers towards ministry officials. - Lack of adequate commitment of the supervisors themselves. The study revealed that, most of the Inspectorate staff had Teachers’ Certificate (T.C) and Higher Teachers’ Certificate with only a small number who are graduates, most of the respondents are within ages 40 – 49 which a youthful age is, the respondents have some amount of working experience which can guide their work as supervisors, that the work load of the supervisors is too much as they are expected to supervise many schools with limited staff, The Inspectorate staff especially supervisors have challenges to cope within terms of capacity, resource materials and even training, the supervision is mostly done on monthly basis, the bulk of the supervision activities are record checking and general observation of school and the Teacher, the constraints need to be addressed or minimized as suggested and recommended by respondents for future improvement. The study recommended that, Government fulfills her responsibility by providing adequate logistics for supervision exercises. E.g. adequate mobility, overnight allowances for distant schools, stationery, and even fuel for mobility, that recruitment process for supervisors and Inspectors be revisited and reviewed for quality selection of Inspectorate personnel, in- Service Training with regards Inspectors professional needs should be organized by the Ministry of Education to equip them for quality work, supervisors and school authorities to work hard for progress of the children or learners in schools.