As sanctions for those convicted of sex offenses have increased over recent years, the risk for reoffense presented by social isolation increases. Because most jurisdictions struggle with how best to manage and reintegrate sex offenders, this study analyzes bureaucratic and contextual issues with arranging community-based reintegration programs. Specifically, this qualitative, process-oriented study examines and compares Circles of Support & Accountability (CoSA) programs from the United States (specifically, Vermont) and New Zealand. CoSAs provide support for medium- to high-risk sex offenders as they are released to communities. The programs are compared with regard to their structures, the relationship to Corrections, the role of communities, and core members’ reentry challenges. The implications of each configuration are explored. As most of the existing research on CoSAs is focused on recidivism, and as the U.S. federal government is expanding the use of CoSA, this article fills a void in our understanding of the role that communities can play in reintegrating sexual offenders and how program structures shape reentry.