This document summarizes a presentation on working with the criminal justice system to educate and enroll the recently incarcerated in health insurance. It discusses why focusing on this population matters for health and cost savings. Examples of initiatives in Kentucky, New York, Arizona and Illinois are provided. The document offers tips on getting started, including researching the landscape, exploring opportunities at different points of the criminal justice system, and forming partnerships. Suggestions are made for potential partners within and outside the criminal justice system. Maintaining momentum is discussed, such as identifying and addressing barriers, leveraging existing resources, tailoring activities based on partners' needs, and assigning tasks. Best practices include various outreach and enrollment strategies.