Chronic pain in Canadian Veterans is twice that of the general population and the prevalence of their related mental health concerns is alarmingly high. This likely puts their children at an increased risk of developing pain and mental health problems that can pervasively impact daily life and persist into adulthood. Pain care and military culture of (acute and chronic) pain has been identified as a top priority of Canadian Veterans. This study aimed to gain an in-depth understanding of the pain experiences of Canadian Armed Forces (CAF) families. Thirty-five semi-structured qualitative interviews were conducted. Demographic information was collected; age, gender, and ethnicity were reported. Twelve CAF members/Veterans, 17 youth, and six spouses were interviewed. Ninety-two percent of Veteran participants reported chronic pain. Reflexive thematic analyses generated four themes: i) Military mindset: herd culture and solider identity, ii) The culture of pain within military families, iii) Inseparability of mental health and pain, iv) Breaking the cycle and shifting the military mindset. Military culture and identity create a unique context within which pain expression and experience is integrally shaped within these families. This study sheds light on how pain is experienced and perceived within military families and can inform research on and efforts to foster resilience in these families. PERSPECTIVE: This is the first qualitative study to explore the lived experiences of pain in Canadian military families. Findings underscore the key role that military culture and identity plays in how pain is experienced and perceived in all family members.