Although people with gambling problems are now recognised to be among those groups of people at increased risk of homelessness, little research has explored their experiences. This qualitative interpretive study explored the experiences of people who were homeless and had gambling problems, and the housing and gambling service providers assisting them. In-depth interviews were conducted with 17 service users and 18 service providers. A key finding was that gambling problems among those experiencing homelessness are often hidden; few people presented to housing services admitting to gambling problems. Shame, stigma, and identity issues were described as the main reasons service users did not disclose their gambling activities. The research highlighted that the relationship between service providers and service users was infused with power imbalances and shaped by social discourses and policies that demand self-responsibility and hinder information sharing between service providers and service users.