The supervision of driving while intoxicated/impaired (DWI) offenders composes a large share of probation officer’s caseloads. Crime and justice researchers have made tremendous advances in the ability to classify offenders according to general recidivism, with the Level of Service Inventory–Revised (LSI-R) being one of the most tested instruments used by community corrections officers. There has yet to emerge a risk assessment tool designed to classify DWI offenders according to their likelihood to be arrested for multiple DWIs. This article estimates a series of multinomial logistic regression models to identify differences between one-time DWI offenders and chronic DWI offenders. The central independent variables are the items on the LSI-R and a popular alcohol and substance abuse screener (Adult Substance Use Survey [ASUS]), while controlling for age, race, gender, and marital status. These instruments are important tools to classify DWI offenders, and the results suggest that the community corrections field (including the offenders supervised) would benefit from a risk assessment tool to classify DWI offenders.