Justice-involved young adult (JIYA) men are at high risk for HIV, yet frequently do not access HIV services. A better understanding of testing behaviors and motivation, as well as facilitators and barriers to testing is necessary for treatment-as-prevention approaches to be implemented among JIYA. Seventeen JIYA men and nine staff were recruited from three alternative sentencing programs (ASPs). In-depth interviews and a staff focus group explored HIV risk and testing uptake behaviors. Narratives from JIYA demonstrated a lack of connection among HIV risk and behavior, views on testing, and knowledge of PreP. Youth and staff also disclosed various youth and environmental/structural barriers to HIV testing. The justice system may be a crucial point of intervention to reduce HIV risk and promote HIV testing with interventions targeted to the needs of JIYA.