Introduction: A third of Canadian Armed Forces veterans report difficulty adjusting to post-military life. Moreover, an estimated 40% of Canadian veterans live with chronic pain, which is likely associated with greater needs during the transition from military to civilian life. This review explored challenges and transition needs among military personnel living with chronic pain as they return to civilian life. Methods: We searched MEDLINE, EMBASE, CINAHL, Scopus, and Web of Science from inception to July 2022, for qualitative, observational, and mixed-method studies exploring transition needs among military veterans released with chronic pain. Reviewers, working independently and in duplicate, conducted screening and used a standardized and pilot-tested data collection form to extract data from all included studies. Content analysis was used to create a coding template to identify patterns in challenges and unmet needs of veterans transitioning to civilian life, and we summarized our findings in a descriptive manner. Results: Of 10,532 unique citations, we identified 43 studies that reported transition challenges and needs of military personnel; however, none were specific to individuals released with chronic pain. Most studies (41 of 43; 95%) focused on military personnel in general, with one study enrolling individuals with traumatic brain injury and another including homeless veterans. We identified military-to-civilian challenges in seven areas: (1) identity, (2) interpersonal interactions/relationships, (3) employment, (4) education, (5) finances, (6) self-care and mental health, and (7) accessing services and care. Conclusions: Military personnel who transition to civilian life report several important challenges; however, the generalizability to individuals released with chronic pain is uncertain. Further research is needed to better understand the transition experiences of veterans with chronic pain to best address their needs and enhance their well-being.