Against a burgeoning worldwide discourse on the psychological and emotional impact of HIV&AIDS on children’s development, I conducted an empirical inquiry to explore how a group of nine orphaned and vulnerable children who were residing in a children’s home negotiated pathways to well-being while they were affected by HIV&AIDS. The study aimed to explore, understand and describe the phenomenon of well-being within the specific context of the child participants’ perspectives of their life-worlds. The study was informed by a qualitative and instrumental case study design within an interpretivist paradigm. In addition, it was guided by a conceptual framework derived from key concepts within the fields of HIV&AIDS, positive psychology, coping and resilience theories. The study employed both inductive and deductive methods for knowledge development. I utilised task-based participatory activities to guide the informal and conversational interviews with the children in the study as the main data generation strategy. I incorporated the use of informal observations and an examination of documentation as additional data generation methods. By means of a thematic analysis approach incorporating principles of the constructivist grounded theory analysis of the children’s expressions, I gained insights that informed my understanding of the children’s perceptions and experiences of well-being, risks, challenges and stressors. Findings indicate that the children in the study experienced risks, challenges and stressors arising from personal illness, stigma, discrimination, orphanhood, residential care, death and bereavement. The study has further revealed that those children who portrayed characteristics of well-being and resilient adaptation utilised psychosocial coping mechanisms. In addition, they were supported and strengthened by their positive intrapersonal characteristics and affirmative relationships that offered emotional and psychosocial support within their environments. The findings of the study suggest that feelings of well-being, hope and optimism might have co-existed with feelings of despair and hopelessness in the daily lives of the children in the study who were affected by HIV&AIDS. I concluded this study by suggesting that the well-being experiences of the children in this study may exist on a continuum and may depend on specific events, occasions or incidents on a day-to-day basis.