Service providers have a unique understanding of older homeless adults’ challenges and service needs. However, research on the experiences of health care providers (HCPs) who work with this population is limited. We aimed to gain a better understanding of the experiences (roles, challenges, and rewards) of HCPs who work with older homeless adults (age 50 and over) in outreach settings. We conducted individual semi-structured interviews with 10 HCPs who worked in these roles. Four themes emerged: (a) the client–provider relationship as an essential building block to HCPs’ work; (b) progression of care that acknowledges the “whole person”; (c) collaboration as integral to providers’ work; and (d) the importance of system navigation. Providers found their work personally and professionally fulfilling but were frustrated by system-level challenges. Findings can be used to identify strategies on how to further support providers in their roles and enhance service provision for older homeless individuals.