Prison management and key stakeholders lack an understanding of how institutional obstacles interfere with probation officers and parole agents' ability in managing offenders to reduce recidivism in a Midwestern state. In 2014, 1 out of 52 adults in the U.S. were under the supervision of probation officers or parole agents. The purpose of this descriptive phenomenological study was to identify the institutional obstacles that exist for probation officers and parole agents in terms of their lived experiences in their jobs. The participants were 5 probation officers and 6 parole agents from a municipal district in a county in a Midwestern state. The conceptual framework that grounds this descriptive phenomenological study is Meadows' three concepts of systems thinking (elements, interconnections, and purpose). The data collection process involved in-depth interviews and field notes. One hundred percent of the participants identified several themes as institutional obstacles including: lack of community programs, lack of jobs, and heavy caseloads. The implications for positive social change for the key stakeholders identified in the study to reduce recidivism in the criminal justice system were to remove the institutional barriers outlined in the themes and improve institutional practices. Making policy reforms that included drug and alcohol treatment, addressing the issue of prison authority and the creation of rehabilitation programs that feature cognitive development would aid in reduction of recidivism.