Insurance enrollment is complex for people living with HIV (PLWH) and people at increased risk for HIV, in part, owing to needing to ensure access to adequate provider networks and appropriate formularies. Insurance for PLWH facilitates access to HIV care/treatment and, ultimately, viral suppression, which has the individual benefit of longevity and the public health benefit of decreased HIV transmission. For people at increased risk for HIV, access to insurance facilitates improved access to HIV biomedical prevention, which has the individual benefit of elimination of transmission risk and the public health benefit of decreased HIV transmission. The objective of this study was to explore perceptions of priorities related to plan navigation, barriers and facilitators for enrolling and maintaining insurance coverage, and questions related to regional, state, and federal policies impacting plans provided both on and off the Affordable Care Act (ACA) marketplace. We interviewed a national sample of assisters ( n = 40), who specialize in insurance plan selection for these populations. We found that assisters tailor their approaches to HIV-specific and person-specific concerns by navigating challenges related to affordability, formularies, and provider networks. In a complex coverage landscape during a time of uncertainty about the long-term future of the ACA, assisters have mastered the ability to simplify the insurance selection process for a vulnerable population. Assisters have excelled at incorporating insurance literacy education and encouraging client engagement in the process. Assisters play an essential role in the current complicated and fragmented United States' health care delivery system for PLWH and people at increased risk for HIV and could be incorporated into the Ending the HIV Epidemic initiative.