This study is grounded in the importance of students' psychosocial development in Islamic educational institutions, in which madrasah headmaster leadership based on Islamic values plays a strategic role. This study aims to describe the implementation of Islamic values in madrasah headmaster leadership for students' psychosocial development at MTsN 1 Bengkalis and to identify its supporting and inhibiting factors. This research employed a descriptive qualitative method with a case study approach. Data were collected through semi-structured interviews, observation, and documentation involving the headmaster, the vice head of student affairs, guidance and counseling teachers, homeroom teachers, and students as informants, and were analyzed using the interactive model of Miles, Huberman, and Saldana. The results show that the implementation of Islamic values is manifested through four core values: amanah (trustworthiness), reflected in the headmaster's responsibility for supervising and guiding students in coordination with counseling teachers; adil (justice), reflected in the equal enforcement of school regulations; musyawarah (deliberation), reflected in the gradual involvement of various parties in guidance-related decisions; and keteladanan (exemplary conduct), reflected in the headmaster's discipline and courtesy. Supporting factors include cooperation among all school components and religious habituation programs, while inhibiting factors include students' lack of openness, large student numbers, and diverse student backgrounds. The implementation of Islamic values in madrasah leadership thus plays an important role in shaping students' discipline, responsibility, and social interaction skills.