Background The emergence of a large population of orphaned youth in sub-Saharan Africa is due to the natural maturity of orphaned children. Research indicates that orphaned youth face more negative psychosocial challenges than their younger counterparts do. Furthermore, these challenges are intensified for early school leavers. This paper describes how experiencing maternal death affects the psychosocial wellbeing of orphaned youth who left school before completing high school. Methods An exploratory qualitative study was undertaken among purposively sampled orphaned youth using in-depth interviews with open-ended questions. Fifty participants were recruited through social workers, community based organisations, and tribal authorities in a rural local municipality of Mpumalanga Province, South Africa. All data analyses were performed using NVivo10, following an inductive thematic approach. Results The narratives with the participants revealed that they live in a socially depressed environment and are subjected to extreme poverty characterised by frequent hunger. Furthermore, they do not enjoy family support and when they live with their extended families, they experience ill treatment and unsympathetic gestures. The death of their mothers has made a negative psychological impact on their psychosocial wellbeing, resulting in the development of internalising depressive symptoms. They suffer from emotional distress and prolonged bereavement characterised by perpetual yearning for the mother and, they resort to silence as a coping strategy. The study established that they were forced to leave school early for a variety of reasons. However, leaving school early became a major stressor and contributed to their negative psychosocial wellbeing. Conclusion Maternal death has a negative impact on the psychosocial wellbeing of the participants even after they have crossed the 18 years threshold of orphan hood. Yearning for their mothers negatively affected their ability to develop coping strategies, which led to isolation, sadness, hopelessness, lack of peace, and fear of an uncertain future. The lack of routine screening for mental health in schools and other settings in South Africa increases their vulnerability to undiagnosed depression. The school health services should develop interventions for mental health screening in schools. For early school leavers, relevant policies should consider the continuation of support through NGOs and community networks.