This study explored the lived experiences of UK Armed Forces veterans with gambling-related harm. Specifically, the study examined how military culture, institutional practices, and transitions to civilian life influenced gambling behaviours and prevented help-seeking, and the long-term impact on veterans’ well-being. A total of 14 UK Armed Forces veterans were interviewed. The researchers identified four interconnected themes: (1) normalization of gambling in civilian and military contexts; (2) gambling as a way to cope; (3) stigma and fear of repercussions as barriers to help-seeking; and (4) escalation of gambling post-military.