Given the extent to which our society values education, it is perplexing to learn that we continue to struggle to provide all children, especially homeless children, an adequate education. This troubling issue is the focus of this paper. Specifically, this paper will center around two basic questions; 1) what has the legal system done to ensure that homeless children receive an adequate education, and 2) what might be done, legally, to advocate for the educational well-being of such children? In addressing these two questions, this paper will begin by problematizing the definition of homelessness and by analyzing some national statistics on homelessness and homeless education. It will go on to discuss a few barriers to resolving the problem of homeless education. Then, it will examine two potential remedies to this problem. The first is the McKinney-Vento Homeless Assistance Act. The second is an alternative schooling arrangement that is uniquely designed to address the educational needs of homeless students. Ultimately, I hope to show that homeless children and families face a number of debilitating barriers to receiving an adequate education and that while the available remedies to these barriers (legal and non-legal) have offered some relief, they are not without problems.