This article examines the impacts of Opportunity New York City-Family Rewards, the first holistic conditional cash transfer (CCT) program evaluated in the United States, on parental financial investments in children, and high school students' academic time use, motivations and self-beliefs, and achievement outcomes. Family Rewards, launched by the Center for Economic Opportunity in the Mayor's Office of the City of New York in 2007 and codesigned and evaluated by MDRC, offered cash assistance to low-income families conditioned on family investments in three areas: children's education, family preventive health care, and parents' employment. Results that rely on a random assignment design find that Family Rewards resulted in statistically significant increases in parental spending and saving on education for all students, and increased savings for those students most academically prepared at baseline and for girls, as well as statistically significant increases in academic time use and achievement outcomes for these same academically prepared students. There were no impacts on student motivations and self-beliefs. Implications are discussed for conditional cash transfer programs as well as for interventions targeting high-risk children and families.