Guilty pleas have come to resolve all but a fraction of federal criminal cases. So for most federal defendants, sentencing is the criminal justice process’s most important phase. That phase begins with the calculation of a recommended sentencing range based on the U.S. Sentencing Guidelines. If a defendant has previously committed two violent crimes or drug offenses, the Guidelines designate him a career offender and drastically enhance his recommended sentencing range. The range is only advisory, but judges must consult and account for the range, and it plays an unquestionably significant role in the defendant’s ultimate sentence. What if the Supreme Court later clarifies that the defendant’s crimes were not career offender predicates after all? What if the correct inputs would have yielded a shorter sentence?

This Note examines remedies for mistakes like erroneously applying the career offender enhancement. It begins by exploring the federal sentencing system’s background and the available remedies for sentencing errors in general, including some remedies grounded in a due process right to be sentenced based on accurate information. It discusses sentencing and appellate-review practices since the Supreme Court made the Guidelines advisory, and observes how courts of appeals have treated those practices—erroneous career offender enhancements are generally curable on direct appeal, but recent appellate decisions have denied relief to prisoners who are subjected to the same errors but whose sentences had already become final. This discussion concludes by scrutinizing those cases and discussing them in the context of concerns for due process and fundamental fairness.

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