Adolescence is a complex developmental stage with challenges that affect transitioning to adulthood. The success in managing the transition depends on personal capabilities, circumstances, and support systems. Contextual situations in adolescent development are understudied in developing countries. In this qualitative study, we explored what South African Grade 10 to 12 adolescents perceived to be the factors influencing their experience of psychosocial challenges at home and at school. Participants (22 Grade 10-12 learners) completed an open-ended survey structured as a written interview. Thematic analysis of the data revealed 2 main themes: home life situations (household financial difficulties, unfavourable living conditions, time-inflexible house chores, poor parent-child relationships, lack of support from families), and school life situations (peers' inappropriate behaviour, perceptions of ineffective school leadership, teachers' low work enthusiasm and commitment, insufficient school resources, unsafe and unfavourable geographical conditions). The findings suggest a need for psychosocial intervention by school social workers at family and school levels to support adolescents in negotiating their psychosocial developmental transition to young adulthood. The departments of education, social development and health, the police services, and non-governmental organisations (NGOs) should collaborate to establish school programmes addressing learners' disruptive behaviour and school safety concerns.