Character education (CE) in secondary schools is one of the educational programs aimed to anticipate the tendency of moral perversion, as a result of moral decadence. Various forms of moral deviations that occur among high school students result in them being alienated from life because they conflict with cultural norms, school discipline, and life ethics in society. This article aims to discuss the relation of character values reinforcement and the principal's transformational leadership strategy to shape student characters in a descriptive-critical manner. The objectives of this study are school strategies in optimizing the implementation of character education reinforcement. This research uses a qualitative method with a case study design. The instrument of data collection was through in-depth interviews, observation, and documentation studies. Data analysis used a modified analytic analysis method. Meanwhile, the data validity measurement was based on the level of credibility, transferability, dependability, and confirmability. The results emphasize the importance of shaping student character as an anticipatory step to minimize moral distortions among high school students, and the effectiveness of the principal's transformational leadership role in optimizing the implementation of character education programs (CEP) in schools.