This study examines how academic supervision can move beyond administrative compliance to support the professional learning of Islamic Education teachers within a madrasah ecosystem integrated with a foundation and an Islamic boarding school. Using an interpretive qualitative single-case study design, the research was conducted at MA Khozinatul Ulum Blora. Data were collected through semi-structured interviews, observations, and document analysis involving the madrasah principal, seven Islamic Education teachers, the foundation chair, the pesantren leader, and students as triangulation informants. The data were analyzed using the interactive model of Miles, Huberman, and Saldaña. The findings show that supervision operated through both formal and informal mechanisms, while its capacity to foster professional learning depended on feedback quality, trust, openness, reflection, teacher agency, and follow-up. Dialogical feedback encouraged pedagogical improvement, whereas predominantly evaluative feedback tended to produce compliance and administrative adjustment. The interaction among the madrasah, foundation, and pesantren also shaped a form of professionalism that combined pedagogical, institutional, and moral dimensions. These findings inform the proposed Relational–Reflective Supervisory Learning Model, which explains how supervision can be transformed into a pathway toward teacher professionalism.