Objective: This qualitative study aimed to describe how educators and parents engage with students on health issues within the context of the Healthy School Approach in a disadvantaged Quebec school. Method: Individual interviews were conducted at the school setting with both educators ( n = 5) and parents ( n = 5) during the school year of 2010–2011. The interview protocol was based on Hoover-Dempsey, Walker and Ice’s (2010) revised theoretical model of the involvement process and more precisely on the mechanisms of influence, modelling, reinforcement, teaching and encouragements. Results: Findings indicate that educators’ and parents’ actions tend to involve modelling and encouragements in particular, with the main emphasis on physical activity and nutrition. Educators stress the importance of grounding their health actions in school activities related to the school project, whereas parents believe that their participation as volunteers in the various health-related activities organized at school significantly helps their efforts to support their child. Results highlight the parents’ undeniable contribution to children’s health within current educational systems. Conclusion: In their conclusion, the authors put into light the importance of two challenging denominators: (1) a shared vision of health; and (2) coherent health education actions in a disadvantaged environment.