The effects of orphaning on adolescents girls are well documented in literature. Adolescents orphaned by AIDS have particular vulnerabilities to a range of mental health difficulties and with that they face specific challenges that include stigma and discrimination, poverty, school drop-out and sexual and labour exploitation. However, there is scarcity of information on how these challenges affect their transition into adulthood. To explore challenges faced by orphaned adolescent girls and to describe approaches used in their transition into adulthood, semi-structured in-depth interviews based on Schlossberg’s Transition Theory (1981) were conducted with 10 adolescent girls orphaned by AIDS. Thematic analysis using Collaizzi’s seven steps of data analysis was utilised. Powerlessness, anxiety, poor negotiation skills; and poor communications were among the challenges mentioned by orphaned adolescent girls. New approaches used in the study included education on problem-solving skills, communication skills; interpersonal relationships and continuous counselling. Recommendations for new policy initiatives are also given.