The goal of this article is to describe the results of interviews with twenty-five parents of children living and working on dairy farms. The interviews sought to uncover farm parent perspectives and experiences pertaining to raising a kid on the farm and around livestock as well as the risks and benefits involved. Parent perspectives of the risk associated with child-livestock interactions were often uninformed by evidence-based guidelines. Instead, parents showcased a relational understanding of risk primarily informed by their highly localized knowledge and experience. We argue that most dairy farm parents understand the risks associated with child-livestock interactions; however, whether these potential hazards prevent parents from allowing a child to complete a livestock-related task is dependent on complex—though well-rehearsed—processes of risk evaluation. Further, the farm parents we interviewed considered the risks and benefits of child-livestock interactions to be interwoven. We conclude by contextualizing the utility of our findings for developing effective youth agricultural injury prevention interventions and safety messaging materials.