Although students of the Soviet period have long been fascinated with criminality, few works have studied courts and common criminals on the basis of trial records, especially during the nep. Aside from scholarly treatments of show trials, the reasoning behind judicial decisions and criminal pleas has been left to the imagination of Sovietologists. This gap is addressed by examining case files involving the primary form of appeal available to Soviet convicts: cassation. After detailing the evolution of Soviet cassation from its origins in the French Revolution and contextualizing its place in the Soviet justice system, this article embarks on a close reading of convicts’ pleas, prosecutors’ reports, and judges’ written decisions in cassational cases. Cassational appeals are examined to determine how different seats of power within the judiciary sparred over verdicts. Judicial decisions of cassational cases are cross-referenced with legal codes and legislation to determine how Soviet judges applied the law, particularly when considering the social backgrounds of appellants. From the outlook of criminals themselves, the wording of their appeals is analyzed to determine how they understood the law, Soviet society, and what they thought they needed to say to gain redemption. Ultimately, this paper explores how individuals brought before courts understood Soviet power and justice through the lens of criminal appeals during the infancy of the Soviet Union.