Contemporary criminal justice policy in England and Wales has witnessed various resurgences of political interest in resettlement and the short sentence population. This intermittent attentiveness has been mirrored in the circular re-iterations of policy initiatives ostensibly designed to bring greater continuity to the services that administer ‘through the gate’ work. These efforts include the ‘seamless sentence’ of the 1991 Criminal Justice Act; ‘end-to-end offender management’, the creation of The National Offender Management Service (NOMS) and the introduction of custody plus under New Labour; and the current Transforming Rehabilitation (TR) ‘through the gate’ reforms. It is important to analyse these attempts in order to understand why resettlement policy consistently fails to deliver an improved continuity between prisons and probation. This paper argues that resettlement policy has a common thread of issues that inhibit effective resettlement practice. This article will firstly consider the ‘essence’ (Senior and Ward, 2016) of resettlement practice, outlining several key principles that should be central elements for resettlement policy and practice, before providing an overview of these various policy initiatives; examining a common thread of failures in their realisation. This article will then look ahead at the next possible iteration of resettlement policy, ‘offender management in custody’ (OMiC), concluding that despite key changes, this latest policy continues to repeat the errors of past resettlement policy failures.