Housing instability threatens the health and well-being of millions of families across the United States, yet little is known about the characteristics or housing trajectories of at-risk families. To address this gap in our understanding of family risk for housing instability and homelessness, we undertook a qualitative descriptive study utilizing a convenience sample of 16 mothers recruited from a housing service agency living in Detroit and receiving emergency services to avoid homelessness. Participants completed the Brief Patient Health Questionnaire (PHQ), then narrated their life events and reasons for housing instability and disclosed desired interventions for homelessness prevention. Data analysis reveals that women experienced high rates of previously undisclosed trauma, broken family relationships, early parenting responsibilities, social isolation, and system failures that contributed to recurrent episodes of housing instability. We argue that housing instability is a symptom of multiple chronic underlying issues that need more than a temporary financial patch.