This study sought to understand the ways that adult daughters and their parents make sense of the older adult’s aging and one another’s changing roles within the context of the decision to move a parent to a care-related facility. In particular, the decision to move a parent to a care-related facility provides a context for the study of uncertainty, ambivalence, and other concerns connected with role transitions and decision-making difficulties. How older parents and adult daughters communicate about and cope with these challenges was compared. Babrow’s problematic integration theory provides a framework for this research. A qualitative study employing in-depth interviews with 44 residents at continuum-of-care facilities and 12 adult daughters of residents was conducted. Findings indicate that both parents and daughters experience significant problematic integration. However, their attempts to cope are in marked contrast to one another. These differences, along with theoretical and practical implications, are discussed further.