The United States’ legislation and jurisprudence regulating the deportation of legal permanent residents is harsh by many standards. The harshness of the legal regime is particularly acute as it relates to minor drug crimes. Under current U.S. law, possession of a single pill of Xanax leads to mandatory detention and can even lead to deportation. This Note explores the impact that the United States’ drug policy has had on deportation law, the current legislative regime surrounding drug-based deportations, the changing landscape of drug enforcement, and the lack of meaningful protection that current legislation and jurisprudence affords permanent residents facing deportation due to minor drug crimes. Finally, this Note argues that the harshest aspects of the United States’ drug-based deportation laws can be mitigated, either via the legislature or the judiciary, so that only truly dangerous criminal non-citizens face the prospect of mandatory detention and deportation.