Low-income young Black men experience a disproportionate burden of violent injury in the United States. These men face significant disparities in healthcare insurance coverage and access to care. The Affordable Care Act (ACA) created a new healthcare workforce, Navigators and In-Person Assisters (IPAs), to support low-income minority populations with insurance enrollment. Using a longitudinal qualitative case study approach with Navigators and IPAs at the two busiest urban trauma centers in Maryland, this study identifies the culturally and structurally responsive enrollment strategies used by three Navigators/IPAs as they enrolled violently injured young Black men in healthcare insurance coverage. These approaches included gaining their trust and building rapport and engaging female caregivers during enrollment. Navigators and IPAs faced significant barriers, including identity verification, health literacy, privacy and confidentiality, and technological issues. These findings offer novel insight into the vital work performed by Navigators and IPAs, as they attempt to decrease health disparities for young Black male survivors of violence. Despite high rates of victimization due to violent firearm injury, little is known about how this population gains access to healthcare insurance. Although the generalizability of this research may be limited due to the small sample size of participants, the qualitative case study approach offers critical exploratory data suggesting the importance of trauma-informed care in insurance enrollment by Navigators and IPAs. They also emphasize the need to further address structural issues, which affect insurance enrollment and thus undermine the well-being of young Black men who have survived violent injury.