Probation and parole officers are assigned the responsibility of supervising convicted criminals in a community setting in such a way that the competing goals of punishment, public safety, offender rehabilitation, and deterrence are achieved. All the while, these tasks are accomplished within the confines of shrinking budgets, large case loads, increasingly high-risk offenders, low occupational prestige, and considerable political and public scrutiny. These competing demands often result in especially high levels of work-related stress. The point of this research is to consider the divergence in occupational stress among probation/parole officers and whether or not they felt educationally prepared for their job. The data for this study were collected during a two-month study period which began on March 15, 2005. Data were collected non-randomly through a national Internet based survey of active probation/parole officers. This study considers a sub-sample of 2, 364 officers from fifteen states. The results show probation/parole officers who feel educationally underprepared are likely to experience higher levels of occupational stress and more likely to have negative manifestations of stress than those officers who feel well-prepared.