Military spouses play an important role in enabling military operational effectiveness. Studies show that poor physical and psychological health among military members negatively impacts the well-being of their spouses. However, little is known about the main challenges and protective factors related to the well-being of military spouses dealing with ill or injured military members. Existing research has mostly focused on one perspective—either military members’ or spousal. Therefore, this quantitative study was conducted with a matched (member and spouse) sample (N = 130). The aim of the research was to understand the role of military members’ illness from both the members’ and spousal perspectives, as well as the role of protective factors, including relationship quality and social support, in the well-being of Canadian Armed Forces (CAF) spouses. Hierarchical regression analyses demonstrated that members’ psychological health predicted the psychological health of military spouses. Analyses also revealed that spousal perception of the relationship quality was a key predictor of spousal life satisfaction and psychological distress.