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States continue to rely on conditional release (CR) as an effective and cost-effective way to manage individuals found not guilty by reason of insanity (NGRI). Research has demonstrated that insanity acquittees returning to the community have low recidivism rates and moderately low revocation rates. This study followed 238 individuals found NGRI in Oregon who were evaluated with the Historical, Clinical, Risk-20 (HCR-20; Webster, Douglas, Eaves, & Hart, 1997) and placed in the community on CR. The majority of individuals on CR (n = 157, 66%) maintained their release throughout the entire follow-up period (between 4 and 9 years), but 81 (33.6%) had their release revoked during the follow up. In considering the efficacy of violence risk assessment in predicting CR outcome with NGRI acquittees, the HCR-20 was mostly unrelated to CR outcome. Only two items from the HCR-20, both from the Risk Management scale (exposure to destabilizers and stress) predicted revocation, but not imminence to CR revocation. This paper reconsiders how risk assessments are utilized with insanity acquittees and provides a roadmap for improving risk assessments with this unique population by relying on risk assessment results to plan effective interventions to reduce the likelihood of revocation and violence.