Childhood obesity is a serious public health concern, and although the complexity of this issue is now recognized, programming has yet to consider the interconnected nature of the contributing factors. This study, guided by grounded theory, sought to discover how mothers are attempting to promote health in a seemingly obesogenic environment. Data were collected via 22 semi-structured interviews, 55 personal diary entries, and 11 parenting style questionnaires. Constant comparative analysis occurred until theoretical saturation, and strategies to increase trustworthiness were used. Themes included (a) Managing Time, Managing Chaos; (b) Cultural Infatuation with Food; (c) Managing Health from a Distance; (d) Fluctuating Challenges and Supports; (e) Strategies; and (f) Resulting Actions/Interactions. Additionally, a substantive-level theory was developed. Findings highlight the importance of developing contextually relevant, family-based interventions for overweight children and their families, and propose a shift in current program development for this population.