The purpose of the study was to undertake a systematic investigation of the current challenges of supervisors in improving quality education in secondary schools of AkakiKality sub-city. Thus, the study seeks to indicate the roles and practices of supervisors; the major challenges that affect supervisors in improving quality education and what responsibilities and authorities should supervisors have in the process of practicing quality education in the sub-city. The research methodology employed in the study was descriptive survey and used Availability, purposive, stratified and random sampling techniques. One hundred seventy eight respondents, (i.e. 2 sub-city educational officers, 3 sub-city supervisors, 15 principals and vice principals, 46 department heads 49 senior teachers and 63 teachers) were selected from the four secondary schools of the sub-city. Questionnaire, interview, focus group discussion and document analysis were employed to gather the relevant data. Percentage and weighted mean were used as the statistical tools to analyze and interpreted the data. Therefore, finding of the study showed that poor work experience, limited resource, unwisely usage of time, luck of mutual relationship between inbuilt supervisors, sub-city supervisors and teachers. Thus, It is recommended that Supervisors should be taken sufficient training and re training to run their supervisory activities, supervisors may also be motivated with adequate working materials, good working environment with sufficient salaries and allowance equivalent to the work loads. It is also recommended that the way of selecting recruiting supervisors be based on the criteria of civil service and focus on the academic affairs.