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The present study evaluated prison environments and presence of rehabilitation opportunities on strain and readiness for re-entry. Specifically, the study identified whether participation in job training and educational programs are associated with psychological distress and prison rule violations. Data were used from 2016 Survey of Prison Inmates with sample size of 21,017 incarcerated people. Generalized structural equation modeling (GSEM) was employed to understand the relationship between rehabilitative opportunities, psychological distress, and readiness for reentry. GSEM results found individuals who did not participate in job training due to risk management had significantly increased psychological distress. Individuals who did not participate in educational programs due to individual motivation or risk management had significantly lower odds of having rule violations compared to individuals who participated in educational programs. Similarly, individuals who did not participate in job training due to risk management or individual motivation had significantly lower odds of having rule violations than individuals who participated in job training. Indiscriminate rehabilitative programs or inadequate programs may impede the effectiveness of rehabilitation and even escalate the strain for some incarcerated people. Furthermore, overemphasis on security and control within institutions may subvert the rehabilitative ideal, limiting the potential of rehabilitative programs to facilitate reentry.