Multiple chronic conditions (i.e., multimorbidity) increase a person's depressive symptoms more than having one chronic condition. Little is known regarding whether multimorbidity similarly increases the depressive symptoms of one's spouse and whether this depends on type of condition, gender, or both spouses' health status. Analysis of multiple waves of the Health and Retirement Study reveals husband's number of chronic conditions is positively related to wife's depressive symptoms when both spouses are chronically ill. The association between wife's chronic conditions and husband's depressive symptoms is weaker and less robust. Type of chronic condition also matters but which type depends on the gender and health status of both spouses. By highlighting key contexts where chronic conditions are connected to spousal depressive symptoms, this study identifies areas of vulnerability and urges researchers and clinicians to consider multimorbidity when designing and implementing interventions, along with gender, both spouses' chronic conditions, and condition type.