Dropping out of high school culminates a long-term process of disengagement from school and has profound social and economic consequences for students, their families, and their communities. Students who drop out of high school are more likely to be unemployed, to earn less than those who graduate, to be on public assistance, and to end up in prison. The present study examined dropout rates in Kentucky high schools (N = 196), using both quantitative and qualitative procedures. Pearson product-moment correlation coefficients were computed to identify those school-level variables that showed strong relationships to dropout rates. A sample of 20 schools with the highest dropout rates was compared to a sample of 20 schools with the lowest dropout rates using a multivariate analysis of variance. Furthermore, 4 schools from each group were selected as case examples. Information gathered from administrator surveys, staff interviews, and on-site observations provided detailed descriptions of the characteristics of schools with high and low dropout rates. The findings of this study demonstrated that a number of school variables are differentially related to dropout rate. Implications of these findings for school reform are discussed.