Educational borderlands are the physical and/or conceptual landscapes where one must negotiate notions of cultural difference as she or he lives and learns--landscapes that envelop an array of pedagogical and cultural spaces, yet are typically guarded by exclusionary tactics. In this article, we examine how US immigrant youth navigate three "educational borderlands": the geopolitical, institutional, and home community. We also discuss how educators' biased ideologies and actions towards these youth solidify borders and increase inequity. Data from studies of California and North Carolina school communities allow us to extend border crossing theories and address how many immigrant youth confront and resist inequities, negotiate their cultural identities, and enact agency. While emphasizing that borderlands are sites of risk and transformation, we also suggest how educators can draw upon their relative power and privilege to cross borders too, advocate for immigrant youth, and ultimately improve education.