The improvement of education quality still encounters many failures in the implementation stage. Among the causes is inadequate management. Managerial supervision is conducted by madrasah supervisors, involving guidance, monitoring, and performance evaluation of the Madrasah Principal. This study aims to analyze and empirically discover the managerial supervision of supervisors in enhancing the competence of the Al Kautsar Junior High School (MTs) and MTsN Depok City. The method used is qualitative descriptive analysis with a case study type. Data collection was carried out through observation, interviews, documentation study, literature review, and direct researcher participation. The research findings indicate the following: 1) The planning of supervisory managerial activities towards the madrasah principals has clear formulation; 2) The organization of the supervisors' work group structure consists of a chairperson, secretary, treasurer, and members of the supervision team; 3) The implementation of supervision needs to be more in line with the supervision guidelines; 4) The analysis of monitoring and evaluation shows that the follow-up to supervision results is not yet optimal; 5) Among the challenges faced are: the ratio of supervisors to supervised madrasahs is not ideal; differences in terms of competence, the complexity of the madrasah principal's tasks, and the facilities in the supervised madrasahs; and 6) Solutions to overcome these challenges include: improving the supervisor recruitment process; involving high-performing teachers in the recruitment of madrasah principals; fostering a culture of quality as the character of supervisors and madrasah principals; expanding the madrasah budget to enhance the availability of facilities; and finding solutions to budget limitations.