In Massachusetts, more than half a million children (15% of all children) live in poverty, 30% of all children live with parents who lack secure employment, and 41% live in households with high housing cost burdens. This article examines the root causes of poverty and its links to child homelessness in the state. Though the state has a long-standing progressive political legacy, the well-being of low-income families with children continues to decline. The article offers evidence about the extent of child homelessness and its profound effects on Massachusetts children and youth. The interconnectedness of what are usually thought of as separate policy domains—poverty, hunger, homelessness, low-wage work, and low-income families’ access to public work supports—are examined, as is the efficacy of homelessness-prevention interventions. Particular focus is placed on policy solutions for alleviating the root causes of child and family homelessness in Massachusetts.