Despite burgeoning interest in prisoner re‐entry and the “collateral consequences” of criminal convictions, we know little about the practical operation of policies governing the rights and privileges of people with criminal convictions. This study examines New York's Certificates of Relief from Civil Disabilities to explore the workings of the US carceral state at the intersection of criminal and civil law. These certificates remove some legal restrictions accompanying convictions, particularly licensure barriers, and are easier to achieve than pardons; other states have used New York's policy as a model. Interviews with judges and probation officers reveal deep variations in how they understand and award certificates. In some cases, differences stem from informal local agreements, particularly concerning firearms in rural communities; in others, from discretionary judgments in a context of legal ambiguity. These practices demonstrate how specific legal, organizational, and cultural factors contribute to complexity and variation in the US carceral state.