This article discusses a number of administrative dilemmas faced by homeless families. For example, homeless families are often prevented from enrolling their children in public schools due to their inability to provide age, health, and educational records. Another administrative dilemma faced by homeless families is providing the school with an address, phone number, and emergency contact information. Many parents are also unwilling to tell school officials about their homelessness out of fear that the child might be stigmatized in school. Therefore, the parents falsify information. This has its own risks. In addition, these children show signs of depression, low self-esteem, and anger. Depression is common among children who are homeless (Nunez, 1994). These problems are aggravated by the lack of parental support these children receive at school. Topping it all off is the fact that schools simply are not designed with homeless children in mind. While the McKinney Act has attempted to remove some obstacles to education for a growing population of homeless children and while there have been efforts to study various aspects of homelessness, there is an urgent need for better understandings on how best to serve children in shelters. The remainder of the article discusses directions for the future including restructuring shelter programs, introducing shared book reading sessions, creating opportunities for personal narratives, and educational implications for teachers.