Background/Objectives: Military identity serves as a foundational lens through which service members navigate the events of everyday military and civilian life. However, the very process that cultivates a sense of unity and purpose can be a double-edged sword in civilian life. Although the prevalence and transition needs are known, few studies have explored how chronic pain specifically disrupts military identity in depth. This qualitative study explores three distinct trajectories through which Veterans with chronic pain experience identity change. Methods: This study used narrative inquiry involving two sets of in-depth interviews with 20 Veterans. Reflexive thematic analysis was employed to describe and differentiate three distinct trajectories of chronic pain. Results: Veterans with chronic pain experience identity change through three overlapping pain trajectories: (1) traumatic injury -> immediate discharge; (2) misdiagnosed/non-traumatic injury -> delayed discharge; and (3) cumulative wear and tear -> gradual discharge. Regardless of trajectory, chronic pain consistently disrupted military identity and forced Veterans to confront tensions between institutional expectations of stoicism and combat readiness and the physical realities of chronic pain during military service. Those interviewed described experiencing fragmented institutional support, uneven access to care, and the systemic invalidation of pain that did not conform to military ideals. Conclusions: These findings underscore the need for Veteran-centred approaches, including responsive services, comprehensive pain science education throughout military careers, early detection of conditions that can lead to chronic pain, and flexible care pathways tailored to the nuances of each pain trajectory and grounded in military culture and lifestyle.