The aim of this study was to explore how older orphans in youth-headed households (YHHs) experience and respond to maternal death and to examine the strategies they employ to care for their younger siblings. We interviewed 18 older orphans who were purposively selected from YHHs located in informal settlements in the City of Tshwane, South Africa. After the death of their mothers, the orphans lost the family home, lost support from their relatives, lost friendships, lost educational opportunities, and lost childhood. The orphans experienced prolonged pain, sadness, anxieties, fear, loneliness despondency, and deep-rooted and persistent anger towards their mother for dying. They suffered from prolonged bereavement because they had been denied the opportunity to mourn the loss of their parents and yearned persistently but silently for their dead mothers. Dropping out of school to seek employment in order to care for their siblings was one of the main coping strategies that older orphans used. However, dropping out of school early robbed them of their future goals of getting an educational qualification. The orphans had not been prepared for taking on an adult role and were given no support or counselling to help them recover from their parents’ death. Continuous grief counselling should form an integral component of the psychosocial support services that are provided to orphans soon after the death of a parent.