Almost invariably, those who are sentenced to prison are released at some point. The white-collar offenders in this sample who were sentenced to prison were no exception and their attempts to establish themselves in society once again are the focus of this chapter. Following a review of the literature that has detailed offenders’ resettlement experiences, the peculiar challenges faced by white-collar offenders are examined. This chapter asks how white-collar offenders viewed the prospect of release, whether release from prison matched their expectations and how they worked out who they ‘were’ in the world they found themselves in once they had exited prison. The analysis begins with prisoners’ anticipation of their release and the anxiety this engendered. This anxiety gave way to concerns over the course their lives would take following release, but stigma and a curtailing of opportunities were significant obstacles for white-collar offenders to overcome.