Introduction: Analyses of the Canadian Armed Forces Transition and Well-Being Survey (CAFTWS) were conducted to identify the most prominent challenges faced by Canadian Armed Forces (CAF) Veterans during their military to civilian transition, and to assess the importance of various characteristics, including release category and health status, as risk factors for experiencing such challenges. Methods: Prevalence estimates and logistic regression analyses were computed on data from the CAFTWS, which was administered in 2017 to 1,414 Regular Force Veterans released from the CAF in the previous year. Results: Two of seven perceived transition challenges had the strongest associations with difficult post-military adjustment: the loss of military identity (adjusted odds ratio [AOR] = 5.4) and fi nancial preparedness (AOR = 2.3). In adjusted regression analyses, Veterans who had non-commissioned rank, who had primarily served in the army, had 10-19 years of service, had a medical release, and had poor physical or mental health, were more likely to report loss of military identity. Veterans who had junior non-commissioned rank, a medical release, and poor physical or mental health were more likely to report challenges with financial preparedness. Furthermore, we observed significant interaction effects between Veterans' release type and their health status. Discussion: This study extends prior research to inform ongoing efforts to support the well-being of CAF members adjusting to post-service life. Findings emphasize the importance of preparing transitioning service members and civilian communities for the social identity challenges they may encounter. Findings also support the value of programs and services that help prepare transitioning service members with managing fi nances, finding education and employment, relocating, finding health care providers, and understanding benefits and services.