This study reviewed an eight-month trial of implementing offline digital learning at a Juvenile Justice Center in Suva, Fiji, through collaboration between Inspire Pacific, Teacher in a Box, and a Griffith University researcher. The initiative aimed to enhance digital literacy and pedagogy among facilitators using an offline server, while addressing the varying technological competencies of both staff and residents. Key findings included the necessity to adapt training to include basic computer skills for students, language accessibility improvements, and the importance of practical, tailored facilitator development. The trial led to unanticipated positive outcomes, such as increased literacy class attendance, expanded numeracy offerings, and the creation of an aftercare and preventative program outside the center. Overall, the project indicated the potential of collaborative, context-responsive educational initiatives to foster lifelong learning among marginalized youth.