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In the much-maligned 1985 case Williamson County Regional Planning Commission v. Hamilton Bank of Johnson City, the Supreme Court articulated a rule of "ripeness" requiring most Fifth Amendment regulatory- takings claimants to seek 'just compensation" in state court before attempting to litigate in federal court. Williamson County and its progeny have opened a Pandora's box of unforeseen complications, spawning many more questions than they purported to answer. At the forefront is what kind of requirement the rule is anyway. This Article contends that reading Williamson County as grounded in the Constitution (specifically, in Article III or the Fifth Amendment) runs the risk of inflicting considerable and unintentional harm on litigants and the judicial system alike. The rule, therefore, ought to be reconceptualized as a matter of merely "prudential"ripeness. Indeed, the Supreme Court has recently taken a few tentative and unexplained steps in that direction. This Article seeks to justify that shift by demonstrating the superiority of a prudential framing of the requirement with respect to various persistent areas of uncertainty, ranging from so-called "facial" Fifth Amendment challenges to the effect of claim preclusion in state courts. In short, viewing the compensation prong as prudential in nature permits a comparison of competing considerations on a case-by-case basis and, ultimately, allows courts to avoid some of the most surprising and senseless potential implications of alternative understandings.