Academic supervision is often constrained by rigid administrative approaches that lack contextual alignment with madrasah culture. This study aims to analyze the principal’s supervision management strategies in enhancing teacher performance at MA Miftahut Thullab Grobogan. A qualitative case study design was employed, using in-depth interviews, participant observation, and document analysis with the principal, supervisor, and teachers. Data were analyzed interactively through condensation, display, and conclusion drawing. The findings demonstrate that supervision management is systematically carried out through the planning, organizing, implementing, and evaluating stages. Key strategies, comprising reflective coaching, direct supervision, continuous motivation, and periodic evaluation, substantially elevated teacher professionalism and instructional quality. Despite internal constraints, including limited facilities, and external environmental challenges, the principal effectively applied adaptive supervision. This study concludes that a transformative, Islamic-value-based supervision model, integrated with local organizational culture, is essential for achieving sustainable improvements in educational quality within Islamic secondary schools.