In addressing the development of the rehabilitative ideal in the Chilean adult penal system over the last two decades, this chapter pays special attention to two recent legal reforms that declared an explicit interest in promoting and strengthening rehabilitation and reintegration. First, the implementation of the concession system in the early 2000s, which introduced private companies into the management of prisons, and second the enactment of the Law 20.603 in 2013, that established a new scheme of community sentences. These reforms emerged out of crises in the prison system, and while both have brought benefits, the historical problems of recidivism and weak social reintegration remain similar. It is argued that a real solution to those issues requires the strengthening of the rehabilitative ideal in normative, theoretical, practical, and financial terms. The chapter finishes by proposing a few ideas for future directions for policy and practice.