Housing First (HF) represents a fundamental shift in thinking about how to address chronic homelessness that has taken place during the past two decades. Whether and how the logic of HF fits in rural systems of care has not been previously explored in the research literature. Using a case study approach and thematic analysis of accounts from 20 key stakeholders, this study investigated whether and how the introduction of HF into a small, rural state in the Northeastearn United States affected the dominant institutional logic. The overall account by multiple stakeholders remained largely consistent: The introduction of an outside HF program brought new resources and expertise, which resulted in a previously underserved population being effectively engaged in services. The extent to which the introduction of an outside provider with a specific, well-defined HF philosophy fit within the existing social services system was complicated by existing providers’ limited knowledge about or input during the grant submission that provided funding for the HF program. Numerous social forces and concerns regarding limited resources also influenced stakeholder perceptions. The impact of HF on existing institutional logics was not always clearly identified by stakeholders, yet HF’s emphasis on providing service options and allowing for client choice, as well as the demonstrated effectiveness of the approach, emerged as influential. Features of local environments (including systems of care but also funding, political, and cultural contexts) and their potential for triggering transformative change may influence the relative merits of implementing HF services by an outside provider with known expertise or supporting an existing provider to develop the infrastructure and foster a service philosophy based on an HF logic.