Research Findings: Very little research has examined whether the contributions of Head Start’s Family Service Workers (FSWs) and family partnership services influence family and child outcomes. Using data from 215 families in the 2014 Head Start Family and Child Experiences Survey (FACES), this study used structural equation models to examine associations between FSWs’ relationship, empowerment, and communication practices; families’ receipt of income supports; change in parent depression symptoms; and change in child approaches to learning, early literacy, early math, and social skills. FSWs’ practices and family receipt of income supports over the Head Start year were associated with reduced parent depression symptoms. Receipt of income supports also was associated with children’s improved approaches to learning skills. Results suggest that Head Start’s family partnership staff and services can help support parents and children living in poverty, identifying critical elements of successful two-generation programming. Practice or Policy: These findings have implications for Head Start and other two-generation programs targeting families with low incomes and suggest investment in strategies to help families address their financial needs and in staff who families view as supportive. (author abstract)