While research on supported desistance is increasing, little is known about practitioners’ experiences of facilitating change following release in Norway. This article seeks to expand this knowledge through the perspectives of probation caseworkers and staff of penal voluntary organizations. Despite their common challenges and shared ideals, the two groups experience varying ability to assist in change processes. While staff of voluntary organizations practice close to the ideal, caseworkers describe frustration at an increased risk focus and thus a decrease in desistance promotion. In this context, we discuss how two key developments in Norwegian resettlement practice, (1) increased discrepancies between ideals and realities and (2) the blurring of boundaries between penal voluntary organizations and the Correctional Services, are shifting probation work away from supporting desistance.