This article considers the benefits of early and deeper officer engagement, and how we might enhance the reentry process in federal supervision, particularly with the recent passage of the First Step Act (FSA). The authors first discuss what we know about reentry, then discuss the possibility of a reentry-centered vision within federal probation, and consider the holistic approach taken by one U.S. probation office, the Eastern District of Missouri (EDMO), within a modified NIJ framework. We close by presenting principles, based upon research as well as real-life examples, that might inform new national reentry procedures.