The six examples in this report document how Head Start and Early Head Start programs across the country have worked with families, local employers, and community partners to create two-generation opportunities for children and parents to achieve lasting stability and success. Both the case studies and the analyses that follow are designed for two purposes. First, to give examples of what locally-designed success can look like to inspire the work of other early learning programs or adult education and training programs that want to be more deliberate in their own two-generation focus. Second, to inform policymakers and the broad spectrum of stakeholders how strong policies and local flexibility can achieve great things when programs are created and implemented in partnership with families. As national conversations continue, Head Start has a window of opportunity not only to showcase successes but to engage in continued efforts to enhance its collective commitment to families. Beyond implementation, advocacy must work to ensure policies and funding are designed to support proven two-generation efforts. (author abstract)