Prevention of recidivism is the universally accepted goal of the New Zealand/ Aotearoa justice system, the nation’s Department of Corrections, politicians and public (“Our vision goal and priorities reducing re-offending”, New Zealand Department of Corrections, 2015). What can be done within prisons prior to release and then in the community post-release to reduce recidivism needs to be better understood. Parolees endure significant challenges when they transition back to their communities. Finding suitable accommodation, confirming stable employment, and maintaining prosocial support networks rate highly among these challenges (Bucklen & Zajac, 2009). While a high proportion of parolees fail to meet these challenges and recidivate soon after release, there are some who do not. Understanding the factors that enable those who avoid further convictions post-release is an important step in designing interventions and processes that might lead to higher a proportion of parolees similarly succeeding (Polaschek & Yesberg, 2016). Of equal importance is the need to understand the factors that increase parolees’ risks of recidivating. Measures have been designed by researchers to understand first, how men prepare for, and conceptualise, their re- entries and second, how they then experience life on parole. The Release Plan Quality (RPQ) measure was designed to analyse prisoners’ release plans and rate their quality on various metrics. Another measure, the Parole Experiences Measure (PEM) rates the quality of parolees’ experiences during re-entry and transition (Wilson, Kilgour & Polaschek, 2013). This thesis examines the PEM and the RPQ in relation to four recidivism outcomes at one- year post-release, namely; conviction for breach of parole conditions, reconviction for new offending (excluding convictions for breach of parole), new convictions for violence offences and convictions leading to reimprisonment. Logistic regression analysis results indicated that PEM outcomes were more predictive of the four recidivism outcomes than the RPQ results. Better RPQ results did, however, predict better PEM results. PEM results (particularly PEM results from the PEM external circumstances subscale) at the two-month mark post-release were found to best predict the four recidivism outcomes. This indicated that environmental issues external to the parolee such as employment and accommodation were more likely to impact risk of recidivism than internal, personal factors such as mental health and personal attitudes. The effectiveness of the PEM two-month results for predicting the four recidivism outcomes remained after controlling for possible confounding variables. This research suggests first, that parolees who have better release plans will have better experiences when on parole and second that parolees who have early positive experiences on parole particularly in relation to external factors such as employment and accommodation are somewhat more likely to remain crime-free post-release.