People experiencing homelessness (PEH) experience more negative social determinants of health, more health issues, worse health outcomes, and a shorter life expectancy in comparison to their housed counterparts. The prioritization of occupations of survival, combined with inadequate health management and functional literacy skills, often hinder the successful and proactive management of health conditions. Subsequently, PEH often defer addressing their health until crisis occurs. This capstone project piloted novel occupational therapy programming with participants in a medical respite setting where PEH stay temporarily while recovering from illness or injury. The researcher used a strength-based, trauma-informed approach, and functional literacy strategies to implement an intake session and four situated learning sessions with participants that focused on health management skills. Overall, the pilot program was well received, as indicated by comparing pre- to post-session satisfaction survey results: 33% increase in “Very Confident” in medication management; and 66% increase in “Very Confident” in health system navigation. Finally, a majority of the participants evaluated the content and functional literacy strategies taught over each of the four sessions as “Very Useful” or “Useful.” Results of the study suggest that including an occupational therapist on the interprofessional medical respite team would be helpful in supporting homeless patients to learn strategies to manage their health more confidently and proactively.