The learning of classical Islamic texts (kitab kuning) serves as a main pillar of the Islamic educational tradition, designed to deepen students' understanding of primary sources of Islamic law and classical religious doctrines. However, its implementation at the Madrasah Aliyah level faces pedagogical complexities when confronted with the heterogeneity of students' educational backgrounds, particularly graduates of public middle schools (SMP) who lack a foundational grounding in Arabic grammar (nahw and sharf). This study aims to describe and thoroughly analyze the dynamics of kitab kuning learning among public school graduates at MAS Alwashliyah Ismailiyah Medan, encompassing academic difficulties, learning motivation, classroom interactions, and teachers' pedagogical responses. This descriptive qualitative research employing a field case study design collected data through participatory observation, in-depth interviews, and documentation involving the madrasah principal, subject teachers, and students from public school backgrounds. Data were analyzed interactively through data reduction, data display, and conclusion drawing/verification, with data trustworthiness tested using source, technique, and time triangulation. The findings reveal that students' primary difficulties include limited understanding of i'rab (syntactic analysis), classical vocabulary (mufradat), and academic anxiety when reading unvocalized texts (teks gundul). As an adaptive response, teachers implement a combination of the bandongan and sorogan methods, gradual scaffolding guidance, and cooperative learning approaches. Reconciling this ability gap has been shown to sustainably enhance students' motivation and turath (classical heritage) literacy skills within a supportive madrasah environment.