Research concerning children who are overweight has historically focused on providing services to the affected individuals, and limited attention has been paid to their families. Further, childhood obesity prevention and clinical programs continue to be impacted by contextual factors that increase the likelihood of attrition when targeting underserved populations. This paper provides data with relevance for interventions aimed at promoting healthy eating and regular physical activity with low-income families. Participants in a childhood obesity exploratory study provided recommendations to improve programs by reflecting on specific family and contextual issues related to children who are overweight and obese. Following a thematic analysis approach, we conducted semi-structured interviews with 16 low-income, single, female parents. All participants had, at the time of the interview, at least one overweight or obese child between the ages of 3 and 8. We report the critical role of context in the etiology and challenges of childhood obesity among disadvantaged populations. Findings also highlight the need for interventions to be culturally relevant and sensitive and to create opportunities to address and discuss participant experiences of discrimination, cultural factors, and family of origin influences. Interventions that do not address these contextual factors run the risk of being unsuccessful. Our findings are important for mental and public health professionals who are interested in the direct provision of services using a combination of social determinants of systemic perspectives.