The purpose of the study was to explore and understand how orphaned adolescents in grandparent-headed households achieve healthy functioning and how they rise above unfavourable circumstances. In exploring and gaining understanding, the research was approached from an interpertivist stance as it entails an inductive qualitative enquiry suitable to gaining a better understanding of the experiences and perceptions of orphaned adolescents. A qualitative methodological design was followed to ensure that the research questions could be answered. Purposive sample selection was used to select participants for this research study. The sample included nine adolescent orphans who reside in grandparent-headed households and are affiliated with Stanza Bopape Community Centre. Data collection included biographical questions, focus group interview and semi-structured interviews. Five of the nine participants took part in a focus group interview and the remaining four participated in individual semi-structured interviews. All interviews were conducted and transcribed by the researcher. Inductive thematic analyses was utilised to identify themes which emerged from the data. The themes which emerged were: the person I am, the supportive roles in parenting, role models in my life, things that are important to me, the future in me. These themes reflect the factors which contribute to the participants’ resilience and can be deduced as the mediating factors which assist them in achieving healthy functioning. The risks identified are aligned with residing in a township and attending a township school, however these risks were not experienced as demotivating adversities for the participants. They rather viewed them as motivating factors to achieve a better future. Bronfenbrenner’s bio-ecological theory served as the theoretical foundation for the study and it emerged that factors which contribute to the orphaned adolescents’ resilience (maintaining factors) come from various systems. Based on the findings of the study it can be concluded that orphaned adolescents residing in grandparent-headed households, although generally of low socio-economic status, are aware of their challenges and utilise certain processes to strengthen their resilience and overcome their challenges.