This study explored how the U.S. Departments of Housing and Urban Development-Veterans Affairs Supportive Housing (HUD-VASH) program applies Housing First principles in the context of ten single-site programs. Focus group discussions with 64 HUD-VASH staff and community partners explored how the programs were influenced by Housing First principles and specific strategies to implement these principles in a single-site setting. Focus group respondents described resourceful ways that the principles of Housing First were implemented in their programs specifically related to (1) housing choice and structure, (2) separation of housing and services, (3) service philosophy, and (4) service array. Several of the Housing First domains cite the importance of integrated housing and the provision of services off-site; it was of particular interest to learn how single-site programs address these issues logistically. Lessons learned from this study include the importance of leveraging the independent yet overlapping tasks of case management and property management to ensure functional–if not geographic–separation of housing and services; maintaining staff on-site to address Veterans’ needs; working with community service organizations to complement the array of service available to residents; and housing single-site programs in mixed-use buildings.