Since 1965 the purpose of Title I of the federal Elementary and Secondary Education Act has been to improve the educational outcomes of economically disadvantaged students and reduce achievement gaps. This paper presents analysis of data from a nationally representative sample of African American and Latinx kindergartners who attended public schools operating school-wide Title I programs in the 2010–11 school year. The purpose of analysis was to examine the associations between Title I programming and achievement gaps. The results indicated that African American students in high poverty, high minority schools made greater gains in reading in schools that used Title I for reduced class size. African American and Latinx students in high poverty, high minority schools made greater gains in mathematics in schools that used Title I for professional development. Findings were scrutinized via propensity score weighting, which revealed the tangled nature of school context, child and family characteristics, and student learning. Suggestions for future research include random assignment studies and local partnerships to determine effective uses of Title I monies. (Author abstract)