Courts have traditionally held that deportation is a civil proceeding, not a criminal proceeding, and that deportation does not constitute punishment. Consequently, the constitutional limits on punishment do not apply to deportation. In this article, the author argues that in light of the recent amendments made by the Illegal Immigration Reform and Immigrant Responsibility Act of 1996 ("IIRIRA") and several recent Supreme Court decisions, the doctrine that deportation is not punishment is no longer tenable. In some circumstances, deportation has become punishment and therefore at least some constitutional limits on punishment must apply in the deportation context. In a series of recent cases, including United States v. Halper, 490 U.S. 435 (1989), Austin v. United States, 509 U.S. 602 (1993), Department of Revenue v. Kurth Ranch, 511 U.S. 767 (1994), and United States v. Usery, 518 U.S. 267 (1996), the Supreme Court has recognized that there are "quasi-criminal" civil proceedings, that is, civil proceedings that are punitive in their effect. This can occur in a variety of contexts that have traditionally been recognized as civil, including tax cases, forfeitures, and pre-trial detention. If the civil sanction cannot be justified by its remedial purpose, but can only be explained as also serving retributive or deterrent purposes, then the sanction is deemed to be punitive even though it is "civil". In such cases, the civil sanction is subject to constitutional provisions that limit the government's power to impose punishment. The author argues that deportation should not be treated any differently than other civil sanctions. In particular, because the extremely harsh measures adopted by Congress in IIRIRA cannot be explained or justified by the remedial purposes of the legislation, deportation must be regarded as punishment, at least in some cases. As a result, and contrary to the traditionally accepted doctrine, at least some constitutional provisions that limit punishment, including the Eighth Amendment and the Ex Post Facto Clause, apply to some deportation cases. The author also argues that if deportation is to be a truly remedial measure and not punishment, then immigration laws must be amended to allow for waivers of deportation in appropriate cases, similar to the 212(c) waivers that were previously available before the IIRIRA amendments. Such waivers would in effect allow a court to review a case and prevent the deportation if the deportation cannot be justified by the underlying remedial purposes of the statute. Otherwise, where deportation is not justified by the underlying remedial purposes of the statute, deportation is punishment.