Conditional Cash Transfers (CCTs) are an endogenous innovation from Latin America and the Caribbean (LAC) that aims to reduce current poverty while developing the human capital of the next generation, in the attempt to break the intergenerational transmission of poverty. Pioneered in Brazil and Mexico in the late 1990s, by 2011 CCTs had spread to 18 countries in the region and covered as many as 129 million beneficiaries. In this paper, we use administrative and household survey data to document (i) the evolution of CCTs and poverty in LAC, (ii) the relationship between expanded coverage and the quality of targeting and (iii) the change in beneficiary household characteristics. We show that in most countries the transfers represent over 20% of poor beneficiaries’ incomes, and the poverty headcount index would be on average 13% higher, had CCTs not been implemented. A decade of sustained and widespread economic growth has expanded the fiscal space for social assistance. The largest programs (in Brazil, Colombia and Mexico) have achieved coverage rates around 50-55% of the poor. At the same time, economic growth contributed to reducing the incidence of poverty. As a result, the number of CCT beneficiaries overtook the number of poor in the region in 2006 (using a standardized income poverty line of USD 2.5 per day (purchasing-power-parity adjusted)). Higher coverage was accompanied by increasing levels of leakage. For example, the share of non-poor beneficiaries increased from 46% to 65% in Ecuador over the period 2004-10, and from 40% to 61% in Mexico over the period 2002-10. Beneficiaries’ level of education and participation in formal labor markets have increased. Yet, the analysis of household data shows that CCT beneficiaries remain mostly poor or vulnerable, characterized by extremely low levels of schooling and unstable labor market outcomes. Hence, while further expansion of the programs may in many cases be unnecessary, the need for social assistance and human capital development remains high. The transition to the new generation of CCT programs will require focusing on the quality of the services that accompany the transfers, in order to maximize the impact on current and future poverty.