Indeterminate detention (ID) is a high stakes sanction reserved for exceptionally high risk-high need (HRHN) persons who are deemed to pose an undue risk to public safety. It is one of the most extreme measures that is routinely taken by justice systems to manage sexual violence risk and prevent sexual and violent recidivism. Naturally, risk assessment is most frequently employed as a mechanism to keep dangerous people in custody; but seldom is risk assessment viewed as a possible ticket out for men with an ID designation who have made substantive risk changes and whose risk can be safely managed in the community. This article features applications of a dynamic sexual violence risk assessment and treatment planning tool, the Violence Risk Scale-Sexual Offense version (VRS-SO), with ID individuals and other HRHN men, to assess risk in a dynamic manner to inform risk management efforts and release decisions. VRS-SO data on an ID sample are presented along with clinical illustrations of dynamic risk assessment. Several propositions are made with supporting data from VRS-SO normative research with treated sexual offending samples regarding the use of dynamic tools with ID men and the perils and pitfalls of relying solely on static measures. Ultimately, dynamic risk instruments can be used to track progress and monitor risk change over multiple assessments to inform release and reintegration decisions with ID persons. In this regard, dynamic assessment has the potential to help, rather than hinder, reintegration of ID sentenced persons and can inform safe, fair, and humane decisions.