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Objectives: Homelessness is increasingly recognized as a crisis beyond Canada's largest cities where it is most visible, yet little is known about the experience and outcomes associated with rural homelessness. The aims of this study were to explore the experience of housing insecurity and its impact on the health of rural residents, identify the various factors contributing to homelessness in a rural Ontario context, and give voice to people with lived experience about their needs, challenges, and potential solutions to the housing crisis., Methods: This exploratory qualitative study used interpretive description and a critical theory lens. Interviews were conducted with people who were currently experiencing homelessness and key informants in a rural community experiencing a housing crisis. Data collection took place between August 2020 and May 2021. Analysis was inductive and concurrent., Results: Findings from interviews with 27 participants (16 with lived experience and 11 key informants) revealed how the structural and social context contributed to rural homelessness. Barriers to securing rental housing in a tight market were influenced by small-town dynamics and discrimination. These experiences led to feelings of hopelessness, which combined with daily stressors of managing unsuitable living conditions to contribute to deteriorating physical and mental health. Opportunities for tailoring interventions to the rural context include increasing awareness, expanding transportation, improving access to local services, and applying Housing First principles., Conclusion: Interventions to prevent and manage homelessness must be tailored to the unique rural context., (© 2022. The Author(s) under exclusive license to The Canadian Public Health Association.)