Little is known about dental case managers as few programs have been scientifically evaluated. The goal of this study was to explore the impact of dental case manager on retention in dental care and completion of treatment plans, while specifically exploring the number of dental case manager encounters. Fourteen programs enrolled people with HIV/AIDS (PLWHA) in dental care and a longitudinal study between 2007 and 2009. The 758 participants had a total of 2715 encounters with a dental case manager over twelve months: 29% had a single encounter; 21% had two; 27% had 3–4 and; 23% had 5–29 encounters. Adjusting for baseline characteristics, participants receiving more encounters were significantly more likely to complete their Phase 1 treatment plan, be retained in dental care, and experience improvements in overall oral health status. Organizations considering efforts to improve the oral health of vulnerable, hard-to-engage populations should consider these findings when planning interventions.