Although government searches generally must be supported by warrant and probable cause, the Supreme Court rarely has applied this requirement in penal contexts such as prison, probation, and parole. In order to justify the government’s broad search authority in those contexts, the Court has created a patchwork of categorical rules and skewed balancing tests based on search targets’ diminished expectations of privacy. This Note argues that the Court’s current approach is unsound: Broad government search authority is justified in certain penal settings, but only because those settings create compelling government needs, not because the search targets have diminished privacy interests. Penal searches should therefore be analyzed under the “special needs” doctrine, which was designed for just this type of situation—where the government has compelling interests above and beyond those found in typical law enforcement contexts. A special needs analysis would allow courts to address the government’s unique interests without devaluing the strong privacy interests at stake. Most importantly, it would impose an additional safeguard to cabin discretion and protect against harassment: Warrantless penal searches could be performed only with individualized suspicion of wrongdoing or through a neutral, nondiscretionary plan.