The influence of school or family on students’ development is widely recognized as essential. Cultural factors which affect students’ use of information and communication technology (ICT) need to be further explored. This research on digital divide analyzed the interview data from principals, teachers, and students from two Hong Kong junior secondary schools. The main findings suggest that cultural divide at school and home can significantly affect the phenomenon of digital divide in education. The cultural factors in school most associated with high ICT usage were the school principals’ culture and values regarding ICT. Parental values, such as demanding but harmonious parent-child relationship, were the most influential home cultural factors. The results of the study suggest that the phenomenon of digital divide could be eased by previously overlooked gaps in school and family culture. Some suggestions and limitations were also provided in the conclusion.