In 2015 the United States District Court for the District of Hawaii Pretrial Services Office collaborated with Hawa'ii Friends of Restorative Justice (HFRJ), a small Honolulu non-profit, to provide and measure the outcomes of a reentry planning circle process for incarcerated individuals who were either facing a federal prison sentence or had been sentenced to federal prison. In 2017 the pilot was expanded to individuals on probation under the court's jurisdiction. This article uses a case the authors worked on to examine the reentry planning process and the pilot project.