The study sought to identify key issues regarding parental involvement within a health promoting school (HPS) approach directed at addressing children’s nutrition and physical activity. A case study research design was used, involving six primary schools in Auckland, New Zealand. Data were collected via six individual interviews with principals, six group interviews with a total of 26 teachers, 13 focus groups with a total of 92 children, and a survey of 229 parents. The study found that while schools agreed on the importance of schools and parents promoting the same healthy behaviours, there was a lack of agreement on the role of school staff in educating parents. School principals identified issues around managing the food brought from home and the extent to which they should regulate types of food. Parents stressed the importance of modelling healthy food and exercise practices in the home environment but identified factors that often made this difficult, a scenario that did not go unnoticed by their children. It is recommended that parental involvement be encouraged and supported so that schools and families can achieve consistency in health promotion practices across both school and home environments.