Though the U.S. Departments of Housing and Urban Development (HUD) and Veterans Affairs (VA) supportive housing (HUD-VASH) program endeavors to address barriers to Veterans accessing and maintaining housing, participants report challenges that lead to program exits. This study aims to understand participants’ views on the factors contributing to their exits from HUD-VASH, as well as how program staff may respond to challenges. This mixed methods study includes four sources of data: (1) surveys with Veterans, (2) semi-structured interviews with a subsample of surveyed Veterans, (3) Veterans’ administrative data from VA electronic data systems, and (4) focus groups with staff from local public housing authorities and VA case management teams. Veterans reported barriers to housing access (e.g., difficult procedures, lack of communication, lack of affordable and adequate housing stock) and housing maintenance (e.g., program rules, mental health and substance use, access to resources), and staff described strategies devised, at the local level, in response to these issues (e.g., better engagement with property owners, funds for deposits and household goods, increased interagency collaboration through HUD-VASH Boot Camps). Findings can inform communities seeking to eliminate Veteran homelessness through HUD-VASH and other supported housing programs.