This study aims to evaluate teachers’ digital literacy to improve their pedagogical competence at Jabal Rahmah Mulia High School in Medan, as well as to identify supporting factors, inhibiting factors, and the implications of its implementation using the Context, Input, Process, Product (CIPP) evaluation model. The study employed a descriptive qualitative approach using the CIPP evaluation model. Data were collected through observations, in-depth interviews, and a review of documents involving the vice principal for curriculum and teachers. Data analysis involved data reduction, data presentation, and drawing conclusions, while data validity was tested using source and technique triangulation. The results revealed that the evaluation of teachers’ digital literacy has been carried out through instructional supervision, evaluation meetings, and professional discussions. The evaluation is supported by school resources and policies, although it still faces several challenges in its implementation. Research findings indicate that the assessment of digital literacy contributes to improvements in teachers’ pedagogical competencies, the quality of learning, and the development of digital learning in schools. This study produced a model for assessing teachers’ digital literacy in boarding schools that positions teachers as the primary agents in the digitization of learning. This model can serve as a guideline for schools in developing sustainable teacher evaluation and professional development systems to enhance pedagogical competencies and support the transformation of digital learning.