Navigating the HIV and substance use systems of care presents a number of unique challenges, many of which can become more complex depending on a person’s housing, employment, mental health, or economic situation. One system that immediately complicates a person’s access to HIV and/or substance use care is the jail or prison system. This month, the BMC team talks with Dr. Alysse Wurcel, a doctor who provides HIV and substance use care in Massachusetts jails. Among a robust breadth of topics, they cover the complex realities of providing HIV and substance use care for people who are incarcerated; how these complexities are perpetuated and affect a person’s access to care both in and out of the jail and prison system; and how HIV and substance use care in the jail and prison system is slowly starting to change.