A growing body of scholarship links extracurricular participation as a supplement to the curricular programme to optimal learner development with benefits of increased retention for learners at risk of dropout. This article looks at how extracurricular participation is provided to learners residing in a constrained environment. A qualitative investigation was undertaken based on individual interviews conducted at five inner-city secondary schools in Gauteng. The findings show that structured extracurricular provisioning, albeit hampered by contextual constraint relating to scant finances, limited facilities and limited time, was beneficial to learners’ holistic development. Perceived benefits for learners pertained to gained cognitive and social skills, a sense of belonging to the school, pastoral guidance, and the sheer joy of participation in the activities of their choice. The findings contribute to research which argues for sufficient implementation of extracurricular provisioning within context in view of the value of a holistic development of the child.