Probation is the leading form of correctional control in the United States however relatively little is known about the impact of probation on individual behavior, effectiveness in deterring crime, or its impact on communities and public safety. Existing research on probation outcomes narrowly focuses on individual-level characteristics associated with the likelihood of recidivating or evidence-based probation practices associated with lower rates of negative discharge. This study advances scientific research on probation to provide a contextual analysis of probation trends through secondary data analysis examining all closed probation cases (both felony and misdemeanor) in the Adult Probation Department of Cook County, Illinois between 2010 – 2016. The study has three specific aims; first, the study examines the spatial distribution and concentration of adult probationers across Chicago neighborhoods over a 6-year period. Second, the study examines neighborhood-level predictors (violent crime rate, concentrated disadvantage, racial/ ethnic diversity, and residential stability) of probation rate over time. Third, the study evaluates the relationship between individual probation outcomes and the same neighborhood-level factors over time. The following key set of findings emerged from the study; adult probationers predictably clustered in poor neighborhoods with high violent crime rates where most residents are African American. Over time, neighborhood-levels of violent crime, concentrated disadvantage, and racial/ ethnic diversity predicted a change in the number of adults on probation. Similarly, spatially concentrated probation populations predicted an increase in neighborhood levels of concentrated disadvantage and violent crime. Limited evidence was found to indicate that one’s probation outcome is influenced by the neighborhood context in which they are supervised. The study is unique in that it is the first spatial analysis of probation drawing from a longitudinal data set situated within one of the largest probation departments in the country. Second, the study is the first contextual analysis of probation outcomes in its examination of the association between neighborhood-level characteristics and recidivism trends. These research aims in this project have received no attention in the literature merit scientific investigation given the growth of probation populations over the past forty years and emerging concern over the effectiveness of probation in rehabilitating offenders while maintaining public safety.