The National Institute of Justice is seeking new ways to use smartphones and other mobile devices to help offenders returning to the community. It recently funded a Purdue University research team to partner with Tippecanoe County, Indiana, to develop an artificial intelligence-based system to monitor and support offender reentry. That system will be deployed within Tippecanoe County Community Corrections and its data will be analyzed to determine areas for improvement. The study plan calls for testing an artificial intelligence-based Support and Monitoring System (AI-SMS) on offenders who will be provided with smartphones and wearable biometric devices or bracelets. A total of 250 randomly selected offenders will participate in the study, with half assigned to a treatment group and the other half assigned to a control group. This article discusses this research as well as how artificial intelligence can advance a variety of reentry services.