This brief document covers the role of social contexts in shaping the transformation of masculinities in a gender transformative and livelihood strengthening intervention in South Africa. The brief looks at the issue of high HIV incidence and intimate partner violence in urban informal settlements of South Africa, and the role of youthful hypermasculinity that prioritizes sexual dominance and displays of violence. The intervention took the form of a gender transformative and livelihood strengthening intervention to reduce HIV risk and IPV perpetration, and its efficacy was tested in thirty-eight in-depth interviews and three focus groups post-intervention. The results and conclusions are assessed.