The literature suggests that individual characteristics of offenders are related to cognitive patterns before their release from prison. Empirical evidence shows that such cognitions can influence the extent to which offenders take an active role in rehabilitation. Given that many studies upon which these conclusions are made are dated, qualitative, or use bivariate analyses, it is unclear how salient, strong, and significant these associations are. Therefore, the aim of this exploratory study is to identify the factors that are associated with two prelease cognitions, future orientation and readiness for release, and to investigate whether future orientation is associated with greater involvement in structured activities. This study uses survey data collected from a sample of 503 people incarcerated in medium-security prisons in South Carolina in the United States. Ordered logistic regression models reveal that idleness, marital status, and drug dependence are associated with future orientation, while idleness, engagement in work and education, age, marital status, sentence phase, and mental health issues are related to readiness for release. Negative binomial regression shows that future orientation is associated with more extensive involvement in structured activities. Overall, the study concludes that while inmates are generally future-oriented, they are less confident that they are prepared for release from prison. The limitations of this study, including low scale reliabilities for key variables and a substantial amount of missing data, are also discussed.