Between 2008 and 2016, students in an Introduction to Gerontology course were required to complete a dynamic case study project simulating caregiving arrangement decision making. Students were divided into groups representing typical multigenerational families and were required to determine how to develop caregiving arrangements to respond to an older family member’ s changing levels of need. The assignment concluded with students writing a final paper summarizing what they learned. This study examined the themes emerging from student group case study papers to gain an understanding of the challenges students face in understanding the dynamics of making family-based caregiving decisions. This is of particular importance as many students were seeking careers in human services and would be assisting clients in such decision-making processes, as well as involvement in decision making for their own family members. Themes that emerged from group papers and the implications related to gerontology education and policy are discussed.