Serving in the military is a risky and stressful occupation. The nature of military service might be a risk factor for risky behaviour, such as problem gambling. This study examined the lived experiences of serving members of the United Kingdom Royal Air Force (RAF) with problem gambling and help-seeking. A total of 17 currently serving members were interviewed. The findings identified several factors that influenced perceptions and experiences of gambling and help-seeking. These included harmful and protective occupational factors; socio-cultural and personal influences; organizational attitudes towards mental health and help-seeking; and support pathways and provision.