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Career offender sentencing enhancements present difficult questions for courts. One of the most difficult of these questions is deciding what crimes warrant the application of these serious enhancements. Federal courts sentencing defendants often must decide, with little guidance, what offenses constitute a "crime of violent" or "violent felony." On a few occasions, the Supreme Court has stepped in and told lower courts that certain crimes do not fit within these categories, and that their interpretation of the career offender enhancement is incorrect. Often, the recognition of this misapplication of the enhancements occurs years after an individual defendant has been convicted, when all direct appeals have been exhausted. How should a court review a prisoner's collateral challenge to an incorrect career offender sentence? Federal courts are currently debating this issue. Circuit courts have been deeply divided in deciding whether these collateral attacks under 28 U.S.C. § 2255 are cognizable. In order to successfully challenge an erroneous career offender sentence on collateral review, a prisoner must show that the error constituted a 'fundamental miscarriage of justice." This Note argues that such errors meet this standard. Erroneous career offender sentences are not ordinary sentencing errors. These enhancements are powerful tools that sentencing courts use to separate especially violent crimes, and can double the length of a prisoner's sentence. An erroneous application of this enhancement is a fundamental miscarriage of justice.