The onset of digitalization has changed teaching practices in all disciplines; yet those disciplines that entail important cultural or ethical connotations require special consideration. This chapter extends the Technology Acceptance Model (TAM) by incorporating Perceived Engagement (PE) and Perceived Compatibility (PC) to examine the determinants of students’ acceptance of a Learning Management System (LMS) in the setting of Religious Education (RE), which is a prototypical value-sensitive area. A quantitative study was carried out using a sample population of 138 university students to evaluate students’ intentions towards using LMS. The findings revealed that perceived usefulness, perceived ease of use, and attitude have direct relationships with using LMS. Furthermore, perceived engagement and perceived compatibility had a strong influence in terms of perceptions with usability and acceptance. The model offers an exportable framework for other value-bound courses, such as ethics, heritage language maintenance and workplace diversity training, where value alignment and engaging design are key. The results inform educators and platform developers in the shaping of LMS experiences that are sensitive to contextual values while maximizing usability.