Pesantren Darul Muta’allimin is the oldest Islamic boarding school in Aceh Singkil and is currently facing various challenges in its daily operations. These challenges include limited capacity, functional transformation of buildings, physical degradation and the use of less sustainable materials, as well as spatial arrangements that are not responsive to the functional needs of the pesantren. Such conditions affect not only the effectiveness of the educational activities but also the comfort and spatial experience of its users. This study aims to examine the need for redesigning the pesantren through a contextual approach that places functional, environmental, and local cultural aspects as the foundation of the design process. The research adopts an architectural design–based approach with a qualitative-descriptive method, employing direct observation, visual documentation, and spatial analysis of the existing conditions.The findings indicate that the main issues of the pesantren are not merely physical in nature but are also related to spatial pattern, building orientation, lack of integration between buildings, outdoor environment and local character. Based on these findings, the study formulates contextual conceptual principles for the redesign of the pesantren, serving as a basis for the development of spatial layout, building massing, and outdoor spaces. These findings are expected to contribute as a reference for the development and revitalization of traditional pesantren in rural areas with similar socio-cultural characteristics.
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