In 2007, the Center for Economic Opportunity (CEO) in the Mayor's Office of the City of New York mounted the first holistic Conditional Cash Transfer (CCT) initiative in an economically advanced, services rich jurisdiction. The initiative is known as Opportunity NYC-Family Rewards (henceforth "Family Rewards"). CCTs offer cash assistance to needy households, but condition these offers on families' making prestipulated investments in their children's education and health. Inspired by Mexico's pioneering "Progresa" program, the effects of Family Rewards (FR) are being measured via a randomized control trial. Initial findings from the program's early operating period show that the program reduced current poverty and hardship, increased receipt of preventive healthcare, and did not improve school outcomes overall for elementary, middle or high school students overall (Riccio et al., 2010). The current study addresses the following research question: How do key characteristics of schools (size, resources, and perceptions of safety) and neighborhoods (neighborhood SES and racial composition) moderate the impacts of Family Rewards on children's academic achievement, time-use, educational processes, parent financial investment in children's education, and families' poverty status and material hardship? The intervention was aimed at low-income families in six of New York City's highest-poverty communities in the Bronx, Brooklyn and Manhattan. It involved approximately 3,750 families and their children selected for the 18-month survey, half of whom could receive the cash incentives if they meet the required conditions and half who were assigned to a control group. Eligible families had to have incomes at or below 130 percent of the federal poverty level and at least one child in the fourth, seventh, or ninth grade. These ages are widely believed to be at or near the start of critical educational transition years. Preliminary analyses by school quality show some variation in impacts on more process-oriented educational outcomes (e.g., adolescents attending the highest ranked schools are more likely to experience become academically-oriented as a result of FR). In addition, adolescents attending lowest-ranked schools are more likely to experience "increases" in academic motivation and adolescents attending schools ranked in the top third experiencing "reductions" in motivation. This paper will look at three dimensions of the school context that have been shown to influence adolescents' academic achievement: school resources, school size, and perceptions of school safety. Three tables are appended.