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Public health concerns associated with infant feeding have prompted the need to increase breastfeeding rates. To do so, initiatives have been implemented and proven successful in raising breastfeeding initiation rates. However, continued breastfeeding according to official recommendations remains scarce and many mothers feel emotionally burdened by their experience. This commentary thus raises the question about the effects of breastfeeding promotion on the well-being of families and takes a critical look at the strategies being put in place. A conceptual model as well as empirical evidences help better understand the balancing act underlying the decisions related to infant feeding and the risks of promoting breastfeeding without providing adequate support. The context of the transition towards a breastfeeding culture requires setting up services adapted to parents' current needs. An approach taking into account their satisfaction and reinforcing their self-efficacy must be adopted, namely through a more thorough implementation of the Baby-Friendly Initiative. Allocating resources allowing for proper enactment of this approach is essential to increase breastfeeding while ensuring families' well-being.