A parole scheme was created in Chile in 1925, with the aim of modernising the prison system by introducing a mechanism of progressive release that promoted inmates’ social reintegration. Almost a century later, parole is being marginally used and its function of reintegration is questioned. This chapter expects to shed light on the legal framework, practice and experience of parole that make it a controversial tool for desistance and reintegration. The chapter is informed by interviews with two magistrates that have participated in Parole Commissions, four practitioners that have been involved in diverse stages of parole application and granting, and ten parolees. First, we outline the legal scheme of Chilean parole, starting with a brief description of the Criminal Justice System for readers not familiarised with it. In the second part, the experiences of practitioners and parolees are analysed in the light of the desistance framework, showing that the current parole practices do not support and even hinder the process of crime abandonment. Finally, the discussion reflects on the findings and recommends areas of improvement that can contribute to the understanding of parole and to improve its application in Chile.