This study aims to explore the relationship between the context of screening for housing instability and Veterans’ access to services, with the goal of ensuring effective processes to address housing instability among Veterans. This study used administrative data from 100,022 Veterans’ electronic medical records and qualitative data collected during in-depth interviews with 22 health care providers and six Homeless Program staff. A mixed effects logistic regression assessed the relationship between Veterans’ screening experiences and connection with services; qualitative data were analyzed using a grounded theory approach to present providers’ reflections on administering screening for housing instability and responding to Veterans’ positive screens with needed resources. We observed a significant relationship between providers’ roles and location of screening with patients’ timely linkage with services. Providing additional training related to how to conduct the screen and provide required resources, shifting screening responsibilities to providers with more flexibility to address these needs, and embedding supportive services in the care team may improve post-screening linkage with services.