This study aims to examine in-depth the transformational leadership practices of madrasah principals in strengthening character education amidst the dynamics of the digital era, focusing on MTsN 1 Merangin. The urgency of this research is based on the acceleration of educational digitalization, which has not only transformed learning systems and methods but also created new challenges related to the moral and ethical development of students. This research employed a qualitative approach through a case study design. The research informants consisted of the madrasah principal, several teachers, and student representatives. Data were obtained through field observations, in-depth interviews, and document reviews. They were then analyzed through data organization, reduction, interpretation, and verification using triangulation techniques to ensure validity. The research findings indicate that the madrasah principal applies a visionary, inspirational, and collaborative leadership style in integrating character building with the use of learning technology. These practices are realized through the instilling of religious values, modeling digital ethics, and providing coaching-based academic supervision. The use of technology has been proven to support the effectiveness of the learning process, but also presents new issues such as challenges in controlling students' digital behavior and a decrease in sensitivity to media ethics. This study confirms that the synergy between transformational leadership, participatory supervision, and the internalization of Islamic values is a crucial foundation for building a technology-based educational management system that remains oriented toward character formation. ABSTRAK Penelitian ini bertujuan mengkaji secara mendalam praktik kepemimpinan transformasional kepala madrasah dalam memperkuat pendidikan karakter di tengah dinamika era digital, dengan mengambil studi di MTsN 1 Merangin. Urgensi penelitian ini dilandasi oleh percepatan digitalisasi pendidikan yang tidak hanya mengubah sistem dan metode pembelajaran, tetapi juga memunculkan tantangan baru terkait pembinaan moral dan etika peserta didik. Penelitian ini menggunakan pendekatan kualitatif melalui desain studi kasus. Informan penelitian terdiri atas kepala madrasah, sejumlah guru, serta perwakilan siswa. Data diperoleh melalui observasi lapangan, wawancara mendalam, dan telaah dokumen, kemudian dianalisis melalui proses pengorganisasian data, reduksi, interpretasi, dan verifikasi temuan dengan teknik triangulasi guna memastikan validitasnya. Temuan penelitian menunjukkan bahwa kepala madrasah menerapkan pola kepemimpinan yang visioner, inspiratif, dan kolaboratif dalam mengintegrasikan penguatan karakter dengan pemanfaatan teknologi pembelajaran. Praktik tersebut diwujudkan melalui pembiasaan nilai religius, pemberian teladan dalam etika digital, serta supervisi akademik yang bersifat pembinaan. Pemanfaatan teknologi terbukti mendukung efektivitas proses belajar, namun sekaligus menghadirkan persoalan baru seperti tantangan kontrol perilaku digital siswa dan penurunan sensitivitas etika bermedia. Studi ini menegaskan bahwa sinergi antara kepemimpinan transformasional, supervisi partisipatif, dan internalisasi nilai-nilai Islam menjadi fondasi penting dalam membangun sistem manajemen pendidikan berbasis teknologi yang tetap berorientasi pada pembentukan karakter.