The study explores the assignment of probation sentencing packages using a data matching process for 3,031 adult males convicted of a felony in two urban counties. Distinct classes of combinations of probation conditions are identified using latent class analysis, and the influence of race and ethnicity on selection into probation and assignment to these classes is investigated while controlling for other relevant factors. Results indicate legally relevant factors account for much of the racial and ethnic disparity in the initial in/out decision, but not in the assignment of probation conditions. Black probationers are more likely to be assigned to a wider range of combinations of probation conditions, more likely to be assigned to combinations that impose specific restrictions, and more likely to be assigned to classes with longer jail sentences. Findings are discussed as they relate to theoretical perspectives on judicial decision making, discretion in sentencing, and court contexts.