The implementation of character education is an essential strategy for supporting the successful implementation of the Merdeka Curriculum, particularly through history learning. This study aims to examine the implementation of character education in history learning at SMA Negeri 2 Boyolali and to analyze the factors influencing its implementation. The research employed a qualitative approach using a case study design. Data were collected through interviews, observations, and document analysis involving informants selected through purposive sampling. Data credibility was ensured through source and technique triangulation, while data were analyzed using the Miles and Huberman interactive model, including data reduction, data display, and conclusion drawing. The findings indicate that character values have been integrated into all stages of history learning, including lesson planning, classroom implementation, and evaluation. The values promoted include religiosity, nationalism, integrity, mutual cooperation, independence, critical thinking, and creativity. The successful implementation was supported by the flexibility of the Merdeka Curriculum, a conducive school culture, the Adi Pangastuti Program, the integration of character values into teaching materials, the Pancasila Student Profile Strengthening Project (P5), teachers’ competence, and collaboration among all school stakeholders. However, several challenges remain, including students’ diverse characteristics, limited instructional time, the influence of social media and the surrounding environment, insufficient parental involvement, and inadequate supporting facilities. These findings demonstrate that history learning plays an important role in fostering students’ character through contextual and meaningful learning in line with the objectives of the Merdeka Curriculum.