The family is a critical context for youth development. Whether it is through neighborhood, school, or activities, families are critical to determining which spaces youth are accessing and in which spaces they are learning. Some of these determinations are intentional, such as when a parent registers a child to participate in an activity; other determinations are unintentional, such as a neighborhood highway prevents a child from getting to an afterschool activity. Families are also responsible for the more mundane aspects of youth programs such as cost, transportation, and scheduling. Extension is uniquely positioned to support the health and well-being of youth, and in helping meet various challenges through family engagement. Extension has talented staff with skills and expertise in building community partnerships, working within and on behalf of families and communities, and working in partnership with youth, families, and communities to develop new ways of working. This chapter explores ways in which Extension has promoted positive youth development through family engagement and offers new ways of thinking about how Extension might do this work differently going forward.