The transition from military-to-civilian life may be difficult for military members, but early or unplanned release can be especially stressful, and may be associated with different challenges from those who planned their release. This study examined transition challenges, and identified whether associated factors differed by release type. The Canadian Armed Forces (CAF) Transition and Well-being Survey surveyed 1,414 recently released CAF Veterans (86% male; 52% 30‒49 years old; 58% Noncommissioned Members; 51% 20+ years of service; 58% Army) using a stratified random sample. Respondents indicated how challenging they perceived ten items related to the military-to-civilian transition (e.g., financial preparedness). They also were asked about their current health, release type (i.e., medical or non-medical release), demographic, and military characteristics. Results revealed that being female, releasing mid-career, having poorer health, and having fewer social provisions may place all Veterans at higher risk for transition challenges. However, certain correlates, such as age, rank, or education level, may be differentially associated with challenging transitions depending on whether Veterans released for medical or for other reasons. Identifying patterns of correlates for perceived challenges can provide insight into how to best support CAF members who are releasing for varying reasons – whether medically, or other circumstances.