With years of research focusing on soaring incarceration rates, the phenomena of prisoner reentry has been largely overlooked. The majority of incarcerated people will return to the community setting. In fact, millions of recently released offenders are on some form of community based supervision. Today, recidivism is a problem that plagues prisoner reentry. In order to address the challenge of prisoner reentry successfully, reentry initiatives have been established in an attempt to change the way corrections is conceptualized. The purpose of this study was to examine characteristics of probationers that are associated with and predictive of successful reentry. The data gathered for this study was existing data from the United States Probation and Pretrial Services office in the Western District of Pennsylvania. Existing data examined included a sample of probationers who were enrolled in the Federal Workforce Development Program (WFD) and a sample of probationers who were not enrolled in WFD. Chi-square and logistic regression tests were conducted to examine variables that may be associated with or predictive of successful reentry. The variables explored in this study included age, race, gender, type of offense, substance abuse, mental health, employment, education, WFD, and recidivism. Employment was the only variable found to be predictive and significant of successful reentry. Results may have been impacted by the type of sample, sample size, demographics, limited number of contextual variables, and ordinal nature of the data. Recommendations for future research and program implementation are included. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]