The purpose of this study is to learn how adolescent boys from Leandra, South Africa, explain their resilience to drought-related challenges. The reason for the study was to gain insight from young people (specifically black, rural South African adolescents) who are under represented in explanations of resilience—which tend to be dominated by resilience studies from Europe and North America. Furthermore, there are currently insufficient studies about the resilience of adolescent boys to drought. And, because there are few studies that focus on the resilience of adolescent boys who are challenged by drought, I adopted a gender-focused lens (adolescent boys). I adopted an exploratory qualitative study with, more specifically, a phenomenological research design and made use of arts-based methods in collecting the data—followed by an inductive content analysis of the data. Three themes emerged in response to the question of what boys do to support their resilience during times of drought (they engage in sport and creative activities, talk to caring others, and pray to God and have faith in their religion). Two themes emerged in response to what social ecological resources support boys’ resilience within a context of drought (protective service providers and peers). These themes are useful to educational psychology because it highlights that adolescent boys’ resilience is moulded by their social ecology as well as which adaptive coping mechanisms are used by adolescent boys faced by drought.