This article presents a qualitative study of how undocumented students experience a unique dimension of legal oppression in the U.S. that results in diminishing their hope in a country that they consider their home. Throughout this study and with the use of a Critical Legal Studies perspective, the author interrogates the role that U.S. immigration law plays in creating hostile and, many times, hopeless scenarios for undocumented youth trying to receive an education. By identifying the ways that undocumented youth face both de jure and de facto detrimental consequences, this study demonstrates how a double layer of legal oppression is formed that is omnipresent in the minds and lives of undocumented students. It is argued that, as educators, it is important to comprehend that undocumented students live under the constant threat of legal enforcement as they traverse the U.S. educational system from K-12 through college. As classroom instructors, this unique dimension is not always apparent because we either do not know that someone is undocumented, or, unless we are undocumented, we do not sufficiently understand what it means to be undocumented. This article attempts to help better understand this experience through the voices of college-bound, undocumented youth from California and Arizona.