Abstract: Introduction: Limited research has focused on the military-to-civilian transition from the perspective of both Veterans and their spouses and on the role each may play in shaping one another’s experiences during this time. This study is a dyadic analysis of psychosocial factors associated with the experience of challenges during the military-to-civilian transition among Canadian Armed Forces (CAF) Veterans and their spouses. Methods: Analyses were conducted on data from the CAF Transition and Well-being Survey, which assessed well-being among Veterans who recently transitioned out of the CAF and, if applicable, their spouses. Structural equation analyses were performed on couple dyads to investigate the associations of Veterans’ and spouses’ psychosocial attributes with their perceived transition challenges and those of their partners. Results: Veterans’ social support and sense of community belonging were associated with reporting fewer perceived transition challenges, and spouses’ social support was associated with reporting fewer perceived transition challenges. Spouses’ perceived ability to manage stress, social support, and sense of community belonging were associated with Veterans reporting fewer perceived transition challenges, whereas only Veterans’ sense of community belonging was associated with spouses reporting fewer perceived transition challenges. Discussion: Multiple interdependent psychosocial factors may be associated with Veterans and spouses experiencing challenges during the military-to-civilian transition, emphasizing the need for services and programs that can address the needs of both parties to promote mutual readiness for, and support during, this important period of change.