In sub-Saharan Africa, an estimated 23 million adolescents leave school due to poverty, teenage pregnancy, and unspecified illnesses. The reasons for absenteeism are well-known but the factors involved in the decision to return to school have not been analyzed. This study aimed to identify the factors that promote primary school re-entry among chronic adolescent absentees in rural sub-Saharan Africa. Qualitative data were gathered through participant observation, in-depth interviews, and focus group discussions involving nine pupils who returned to school after chronic absenteeism and 140 adult stakeholders in Mbita sub-county, Kenya. Data were analyzed using thematic analysis. The thematic analysis results showed that four factors promoted school re-entry, namely: (1) social norms: “school for a better life”; (2) linkage of community and school; (3) supportive environment; and (4) using discipline to make adolescents serious about their education. School re-entry among chronic absentees in Mbita sub-county is promoted by both community and school factors. It was observed that social norms regarded an education as a “passport to a better life.” Adolescents, teachers, and community leaders view education as a means of improving one’s socio-economic status. Two essential elements of health-promoting schools, a supportive environment and a linkage with community, effectively promoted returning to the school among adolescents. The introduction of health-promoting schools was recommended to implement a school re-entry policy in Kenya effectively.