This paper uses a postmodern family perspective to examine the interaction between Army Casualty Assistance Officers (CAOs) and the families of deceased soldiers. The data we examine are open-ended survey responses of CAOs (N = 188) who assisted bereaved families of soldiers killed in three unrelated air disasters. Five themes emerged from our analysis of the qualitative responses: postmodern family structures, contested definitions of "significant other," language, diversity, and emotion. These themes appear to be related to the difficult demands associated with bereavement work. We argue that the experiences of the CAO are comparable to the experiences of others who may work with the bereaved (e.g., police officers, medical workers, and disaster workers) when working in similar familial contexts.