The Federal Sentencing Guidelines are riddled with policy oversights. In United States v. Kimbrough, the Supreme Court permitted district courts to vary from the Guidelines based on categorical policy disagreements. Yet, although district courts often vary from the Guidelines for individualized reasons, the policy variance power has been underutilized. This Note provides a case study of the history of one obscure Guideline, section 2M5.1, as applied to one particular type of case, a nonmilitary-related embargo violation. The case study exposes the United States Sentencing Commission’s systemic oversights in the history of creating Guideline section 2M5.1 and demonstrates how lawyers and judges can rely on that history on a case-by-case basis to expose categorical problems with Guidelines policy. Employing such a categorical policy approach to supplement an individualized approach promotes fairness, transparency, and feedback for future refinement of the Guidelines.