ABSTRACT Child well-being is particularly relevant to South African social workers given the country’s high rates of violence, poverty, inequality, unemployment, HIV/AIDS, and poor schooling outcomes. Guided by a social constructivist theoretical lens, and located within an interpretive qualitative research design, the aim of the study was to determine whether children’s drawings and teacher interviews can differentiate qualitatively between children with positive well-being and those with compromised well-being. Children aged 6–8 years whose parents/caregivers were recipients of Child Support Grants (CSGs) were asked to draw a picture of themselves and their families and teachers were asked about the children’s functioning. Findings from triangulation of drawings and interviews suggested that while a firm diagnosis of emotional, behavioral, or cognitive disorder could not be reached, it was possible to differentiate between children with positive well-being and those whose well-being appeared to be compromised by developmental delay, learning difficulties, emotional problems, behavioral problems, and/or social issues. It is therefore recommended that social workers make greater use of children’s drawings and educator interviews as assessment tools. However, one should not rely solely on children’s drawings, but should rather combine drawings with child and educator interviews. Findings also highlight the need for South African social workers to develop indicators that are culturally and ecologically applicable to African children.