This study aims to investigate the complex learning problems encountered in Islamic Cultural History (Sejarah Kebudayaan Islam/SKI) subjects at MTsN 5 Pasaman and to evaluate the pedagogical strategies applied by teachers to address these instructional challenges. Despite the curricular mandates of KMA 183 of 2019 and Kurikulum Merdeka toward student-centered learning, SKI instruction frequently faces operational obstacles, including low student reading literacy, high cognitive load from historical memorization, and conventional teaching methods. Employing a qualitative-descriptive approach, data were collected through classroom observations, in-depth interviews with SKI teachers and students, and document analysis of instructional frameworks. The data were analyzed using the interactive model of Miles, Huberman, and SaldaƱa through data reduction, data display, and conclusion drawing, supported by source triangulation for data credibility. The research findings identify two main dimensions of learning problems: internal factors (low historical literacy, student passivity, anxiety in memorizing dates and historical figures, and lack of self-confidence) and external factors (predominance of teacher-centered lecture methods, underutilization of digital visual media, and restricted textbook access outside the classroom). In response, SKI teachers implemented tactical strategies, including heterogeneous group discussions, visual timeline mapping, reflective questioning techniques, verbal motivation, and remedial coaching programs. While these tactical interventions successfully provide short-term instructional relief, the study concludes that sustainable historical engagement requires a broader pedagogical shift toward technology-integrated media, contextual storytelling, and policy support for flexible learning resources.