Parenting stress and parenting practices are key indicators of family relational well-being, yet less is known about these indicators among adolescent mothers in resource-constrained settings. This study draws on cross-sectional survey data from 931 adolescent mother–child dyads in the Eastern Cape, South Africa (first parity 11–19 years). Mothers completed an adapted Parenting Stress Scale and the Parenting Young Children (PARYC) measure, and children were assessed using the Mullen Scales of Early Learning. We examined associations between parenting stress, parenting activities, and developmental functioning using multivariate regression. Adolescent mothers reported elevated stress, shaped by child characteristics, intergenerational caregiving dynamics, and household resource strain. While mothers frequently engaged in playful and responsive activities, they reported greater difficulty with limit setting and proactive parenting behaviors. Children showing age-appropriate cognitive and socio-emotional development were more likely to have mothers who engaged regularly in playful activities and reported higher parenting enjoyment. Associations were small to moderate (ANOVA p<0.001, d=0.48). Findings highlight adolescent parenting as a site of both vulnerability and resilience, suggesting that interventions may be strengthened by addressing stress regulation, playful engagement, intergenerational support, and economic stability as interlinked indicators of family well-being.