For years, people sentenced as children to life in prison with the possibility of parole, and their families, have tried to get Maryland to live up to the promise of second chances that a parole-eligible sentence is intended to provide. However, many barriers exist that stop this from happening. Many criminal justice stakeholders have turned to technology to help make parole decisions through “risk assessment tools.” Also labeled artificial intelligence, these tools have been touted as carrying with them the potential to save a broken system. However, these tools may exacerbate the same problems they are supposed to help solve. They rely on flawed criminal justice data that is not controlled for the institutional vestiges of slavery, de jure and de facto segregation, racial discrimination, and biased policing. In this episode we talk to Earl Young, who was sentenced to life as a young man; James Foulds, Assistant professor in the Department of Information Systems at UMBC; and Sonia Kumar, Senior Staff Attorney at the ACLU of Maryland. What are the barriers to people getting a real opportunity to earn a second chance? What can you do to support meaningful reforms to parole systems, like the deeply flawed system in Maryland?