Health literacy is increasingly understood to be a mediator of chronic disease self-management and health care utilization. However, there has been very little research examining health literacy among incarcerated persons. This study aimed to describe the health literacy and relevant patient characteristics in a recently incarcerated primary care patient population in 12 communities in 6 states and Puerto Rico. Baseline data were collected from 751 individuals through the national Transitions Clinic Network (TCN), a model which utilizes a community health worker (CHW) with a previous history of incarceration to engage previously incarcerated people with chronic medical diseases in medical care upon release. Participants in this study completed study measures during or shortly after their first medical visit in the TCN. Data included demographics, health-related survey responses, and a measure of health literacy, The Newest Vital Sign (NVS). Bivariate and linear regression models were fit to explore associations among health literacy and the time from release to first clinic appointment, number of emergency room visits before first clinic appointment and confidence in adhering to medication. Our study found that almost 60% of the sample had inadequate health literacy. Inadequate health literacy was associated with decreased confidence in taking medications following release and an increased likelihood of visiting the emergency department prior to primary care. Early engagement may improve health risks for this population of individuals that is at high risk of death, acute care utilization, and hospitalization following release.