An experiment in offender reintegration in England and Wales has recently been abandoned following long-standing criticism and conclusions that the probation model on which it is based is ‘irredeemably flawed’ (Her Majesty's Inspectorate [HMI] of Probation, 2019a). Under Transforming Rehabilitation (TR) a series of policy reforms concerning the throughcare and reintegration of offenders were undertaken in England and Wales between 2014 and 2019, which most controversially involved the privatisation of a large proportion of probation services. In this chapter we review the key policy changes under TR, before turning to explore how they worked in practice and discussing the adverse effects of this policy on third-sector organisations (TSOs), probation services, staff and offenders. The chapter concludes by examining the lessons we can learn from this failed initiative.