We explored the hypothesis that the Programme of Advancement through Health and Education (PATH), Jamaica's conditional cash transfer program, contributes to breaking the inter-generational poverty cycle by placing its urban beneficiaries on a higher educational trajectory. Using a regression discontinuity design, we found that PATH urban male beneficiaries who sat the Grade Six Achievement Test (GSAT) over the period 2010-2014 performed better on the test (scoring 16.03 points, or 3.6%, higher than non-beneficiaries); consequently, they were placed in better secondary schools (1.5 percentiles higher in a national school ranking based on placed students' GSAT scores). In contrast, we found no significant impact for urban girls.