Character education reinforcement in secondary schools is one of the educational programmes aimed at anticipating 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. In this article we aim to discuss the relation of character value reinforcement and the principal's transformational leadership strategy to shape students' characters in a descriptive-critical manner. The objective of this study was investigating school strategies for optimising the implementation of character education reinforcement. In this research we used a qualitative method with a case study design. The data validity measurement was based on the levels of credibility, transferability, dependability, and confirmability. The results emphasise the importance of shaping student character as an anticipatory step to minimise moral distortions among high school students, and the effectiveness of the principal's transformational leadership role in optimising the implementation of education programmes for the strengthening of students' characters in schools.