This study explores in depth interviews of parents, teachers, and educators within the confined geographical boundary of Santa Cruz County, California in order to offer to the broader community a more concise look at the challenges families and schools face in addressing the issue of family homelessness. The current state of family homelessness is detailed by viewing the data obtained via various measurement methods. In addition, specific barriers and challenges that homeless students and families face outside of and on the school site are explored. The legal policies that support homeless youth and families are described, as well as the literature surrounding supports and other factors that contribute to the success of homeless students and families outside of and on the school campus. Finally, previous research completed that included the voices of homeless students and families, and teachers working with these families is summarized. The data for this study were obtained in video format and were then edited to produce a documentary. Participants included families that were currently or recently homeless, educators who worked with these families directly, and community members who had a direct connection with homeless families in Santa Cruz County. Findings indicated that strong relationships between educators and homeless parents create an environment in which families feel supported. Future research areas are detailed in order to further expand the knowledge base of the experience of homeless students and families as they interact with the education system.