Background: The drastic surge in the number of homeless families in the United States (U.S.) has resulted in an increase in the number of homeless students attending U.S. public schools. Meanwhile, the U.S. public school system is struggling to meet the educational needs of their homeless students. Objective: This study examined the historical trajectory of U.S. federal initiatives that aim to respond to the needs of homeless youth; homeless youth research, classifications and typologies; homeless youth social conditions; and the factors that foster or impede their education. Methods: This study reviewed U.S. federal policies that intend to address homeless youth needs and education; the causes and impact of homelessness on youth; the economics of homelessness; and the relevance of resiliency in improving homeless youth prospects. Results: Despite the enormous challenges homeless youth face, some manage to successfully graduate from high school. While homeless youth are incapable of building or institutionalizing the support networks and structures they need, they are capable of utilizing available support systems within their surroundings. Conclusion: Without responsive structural support this vulnerable population is at high risk of failure. Several federal programs are mandated to assist homeless youth meet their basic needs and education. For these programs to realize their objectives, deliberate efforts must be expanded to assess and evaluate program efficiency. Also, past federal educational initiatives may offer insights on how to better chart and inform the many existing federal homeless youth programs that aim to meet the diverse and complex needs of homeless students.