This study examined gambling trajectories, motivations, and support-seeking behaviours among UK Armed Force veterans and family members. The researchers interviewed six veterans and three family members. The findings highlighted gambling behaviour and recovery of veterans, as well as the impact on, and experiences of, family members. The veterans’ gambling trajectories were shaped by their personal histories, military culture, and post-service transitions. They described how gambling was a part of military life, with gambling being socially encouraged and readily accessible. Gambling also became a way to cope with stress and trauma. Both veterans and family members described severe negative consequences of gambling, including debts and mental health issues. Reasons for delaying seeking help included shame, stigma, and lack of tailored services.