High rates of substance abuse and recidivism and limited in-prison and postrelease treatment access and transitional planning complicate community reintegration. Moreover, drug-related health and social problems are related to treatment outcomes. In the framework of risk-responsivity theory and structured, integrated reentry models, this article argues for new, psychometrically sound assessment tools that are multidimensional, facilitate risk management and service linkages, and combine static and dynamic factors and multiple time frames. The organizational complexity of reentry increases the urgency to develop tools to accurately identify parolee service needs. Such tools will increase knowledge about factors determining or mediating postrelease outcomes.