Education, employment, housing, and substance abuse pose significant problems to the successful reentry of individuals released from prison. The current research project utilized a natural experiment, an oil boom in a Midwestern state, to examine changes in offender reentry and recidivism outcomes overtime. The first part of the study compared a sample of offenders released from prison prior to the oil boom to a sample of offenders released from prison during the highest peak of the oil boom. Comparisons were made on variables known in the literature to be predictive of recidivism during the reentry process; these include risk, education, employment, housing, substance abuse, and treatment. Recidivism was measured as a new conviction, technical violation, and re-incarceration. The follow-up period for both samples was two years. The second part of the study incorporated the perspectives of probation and parole officers. All officers in the Midwestern state were surveyed on their perception of offender reentry and how it may have changed as a result of oil boom influences. Officer attitudes, philosophies, and supervision strategies were analyzed in relation to their perceptions on offender reentry and the oil boom.