Prison conditions and the treatment of incarcerated individuals in Chile have improved a great deal when compared to the end-of-the-dictatorship period at the beginning of the 1990s. Along with rapid societal changes over the last decade, the Chilean prison system has been transformed in many ways. Today, human rights are more visible within the prison system through a variety of indicators, both quantitative and qualitative. On the other hand, it still has pending tasks and faces new challenges, such as: historical deficit on infrastructure and material conditions, violence inside prison walls, insufficient program access, the COVID-19 crisis, changes in its population, or the threat of organized crime. Although Chile is currently under a democratic regime, the authoritarian legacy still persists and can be traced to how the prison system is operated and structured. Today, the prison service depends on the Ministry of Justice and Human Rights and houses about 45,000 incarcerated individuals, a rate of approximately 236 per 100,000 inhabitants (ICPS, 2022). Some have argued that the Chilean prison system is in better shape than neighboring countries, but others criticize its similarities to the rest of the region, which are far from adequate standards when compared to developed countries. This paper utilizes quantitative and qualitative data to describe some of the efforts that have been made to improve the human rights of the incarcerated, critically analyze some pending challenges, and identify current roles and opportunities for social work professionals inside Chilean prisons.