An estimated 1.2 million people in the United States are living with HIV. Of those living with HIV, only 40% are engaged in HIV care, 37% are prescribed antiretroviral therapy (ART), and 30% are virally suppressed. Individual-, interpersonal-, and structural-level factors that represent barriers to engagement along the HIV care continuum are important to identify in order to inform priority areas and interventions. 296 adult residents of Rhode Island living with HIV between November 2015 and January 2016 were asked to participate in an observational study (Ryan White Part B Health Resources and Services Administration-funded consumer needs assessment) to identify the multilevel factors associated with engagement in the HIV care continuum outcomes (i.e., being retained in care, being prescribed ART, adhering to ART, and achieving viral suppression-all in the past 12 months). Multivariable logistic regression models were fit to model the four HIV care continuum outcomes. The majority of participants were over age 30 (92.5%), racial/ethnic minorities (67.1%), cisgender men (56.9%), and identified as straight/heterosexual (60.5%). Overall, 95.2% of participants were retained in care in the past 12 months, 93.0% were prescribed ART, 87.1% were currently adherent to ART, and 68.2% were virally suppressed. Factors positively associated with not being retained in HIV care in the past 12 months included having no income and challenges navigating the HIV care system. Being age 18-29 and having a provider who does not know how to treat people with HIV/AIDS were each positively associated with not being prescribed ART. Factors positively associated with not being adherent to ART included being age 18-29 and substance use in the past 12 months. Finally, having private insurance and having a provider who is not trustworthy were each positively associated with not being virally suppressed. Regardless of the fact that many of the individuals living with HIV in this sample are able to achieve an undetectable viral load, challenges with retention in HIV care and ART adherence threaten to undermine the clinical and public health benefits of treatment as prevention. Future longitudinal research conducted to better understand how to boost the effectiveness of treatment as prevention in this population should focus on examining the unique multilevel factors, polymorbidities, and conditions (mostly social determinants of health including housing, socioeconomic position, etc.) associated with suboptimal engagement across the stages of the HIV care continuum.