Using official school data from a sample of 3,461 students enrolled in Grad Solutions, an Educational Management Organization (EMO), from 2015 through 2018, we conducted a quantitative cross-sectional research design study to understand the predictive nature by which students who dropped out of high school and re-enrolled in Grad Solutions graduated high school. The authors used logistic regression to examine the extent to which students' credits upon enrollment, students' credits remaining after enrollment, mentors' educational background, percentage of mentors' monthly student progress toward graduation, and tenure as a mentor on whether a student graduates or drops out from Grad Solutions. All variables of study significantly predicted p < 0.001 and p < 0.01, an increase and decrease in the odds by which students graduated high school or dropped out of high school. Implications are drawn for designers of mentoring and intervention programs as well as EMOs.