Contextual factors at systemic, organizational, and community levels not only affect individuals’ experiences of homelessness but also impact the implementation of housing programs designed to address this issue. In order to be effective, programs must be culturally appropriate and adapted to fit the needs of the target population (Galavotti et al., 2008; Wandersman et al., 2008). This presentation will discuss the ways in which a Housing First program (HF) on the island of O‘ahu adapted its model to respond to cultural, systemic, and community-level factors. Part of an ongoing four-year program evaluation, this study relied on data from a PhotoVOICE project (PV) with HF clients and in-depth interviews with program staff, case managers, clients, and landlords. Thematic coding of interviews and PV group transcripts revealed that the program made useful, creative adaptions to the model that addressed these contextual issues. For example, the staff explained that the high prevalence of large extended families in Hawai‘i impeded quick placement and client housing choice – important HF model criteria (Watson et al., 2013). Therefore, the program secured acceptable units as they became available so that staff could place families once they were vetted. Additionally, data revealed significant community and landlord stigma toward homeless individuals. However, there was also a public consensus that the island needed “to work together” to solve the “homelessness crisis” (see http://www.staradvertiser.com/homeless-in-hawaii). The program capitalized on the community’s general interest and openness to addressing homelessness by conducting community education designed to reduce stigma. One such educational event included a PV exhibit of clients’ photos and stories. Ultimately, this study showed that HF program implementation was enhanced by a flexible fidelity to the model and the addition of a community education component because these adaptations helped the program respond to contextual and cultural factors.