Research on young people experiencing homelessness often emphasizes the role of abuse, neglect, and rejection from guardians in the process of pushing or forcing young people out of the home. More recently, the research has begun to pay attention to how parents and other family members can remain a part of a young person’s network throughout their homelessness trajectory. Nevertheless, within this literature, questions remain about the impact of ongoing family dynamics on youths’ potential pathways through homelessness. This paper aims to focus on one type of family dynamic in particular, that of the young caregiver experiencing homelessness. The analysis uses interviews with five young people with histories of young caring and homelessness to stimulate future research on how youthful caregiving intersects with the experience of housing instability and youth homelessness. The paper focuses on three main themes: insights into the nature of the family dynamic and the caregiving relationship, discussions about the burden associated with the care relationship, and themes about resilience.