Families caring for children with medical complexity (CMC)—children with multiple chronic conditions requiring frequent hospitalizations, many care specialists, and complicated medication regimens and/or device use—face many challenges in providing the around-the-clock, in-home care their children need. These challenges often result from the mismatch between families’ resources and the work required to provide high-quality care for their children. Families consistently report being under-trained and under-supported in performing necessary, yet complex care tasks, e.g., tracheostomy care. Thus, families are often forced to develop their own solutions to overcome the challenges they face in caring for their CMC in light of the limited resources. This dissertation uses a Human Factors Engineering approach to explore the strategies that families develop to care for their CMC, conceptualizing caregiving as care work that takes place in a care work system, which invariably shapes work processes and outcomes. Specifically, this dissertation expands our understanding of how family-generated strategies relate to the dynamic care work system. Building off previous analyses of a rich dataset of 30 in-home, contextual inquiry-style interviews with families caring for CMC, I conducted an analysis of the relationships between family-generated strategies and work system barriers and facilitators, i.e., factors that hinder or support care work. The results of this dissertation provide theoretical grounds for an expanded conceptual model of family-generated strategies that recognizes that work system facilitators are integrally related to strategies. Further, the study provides practical insight into the work systems of families caring for CMC that can be used to design interventions that support families’ care work and their capacity to adapt, i.e., develop strategies, as needed to ensure the delivery of high-quality care to their child.