This research is motivated by the importance of shaping students' leadership character as an integral part of character education in schools. The Intra-School Student Organization (OSIS) serves as a platform that plays a vital role in developing students' leadership abilities, responsibility, discipline, and social skills. This study aims to: (1) describe the leadership character formed in students through OSIS activities at MA Al-Fattahiyyah, and (2) identify the supporting and inhibiting factors of OSIS in shaping students' leadership character. This study employed a qualitative approach with a descriptive method. The research subjects consisted of the vice principal of student affairs, the OSIS advisor, OSIS committee members, and students actively participating in OSIS activities at MA Al-Fattahiyyah. Data collection techniques were conducted through observation, interviews, and documentation. Data analysis used the Miles and Huberman model, which includes data condensation, data display, and conclusion drawing/verification. The trustworthiness of the data was ensured through the triangulation of sources, techniques, and time. The results demonstrated that OSIS activities contribute significantly to the formation of students' leadership character. The characteristics formed include discipline, responsibility, communication skills, self-confidence, teamwork, decision-making abilities, as well as democratic and noble leadership (akhlakul karimah). The character formation is carried out through habituation, role modeling, the implementation of work programs, organizational evaluations, as well as clear delegation of tasks and responsibilities. Supporting factors in shaping leadership character include supportive school policies, the religious culture of the Islamic boarding school (pesantren), the active role of the OSIS advisor, and solidarity among committee members. Meanwhile, the inhibiting factors consist of schedule conflicts between academic and pesantren activities, students' physical limitations, fluctuating member motivation, and differences of opinion among divisions. Thus, OSIS activities are proven to be an effective means of shaping students' leadership character at MA Al-Fattahiyyah.