A set of motions filed during the COVID-19 pandemic challenged federal judges to consider whether they should always view the duration of imprisonment—as contrasted with prison conditions—as the sole determinant of how much punishment a sentence carries out. Under 18 U.S.C § 3582(c)(1)(A)(i), federal judges may “reduce” already imposed terms of imprisonment upon finding that “extraordinary and compelling reasons” warrant reductions. Prior to 2019, the Bureau of Prisons (BOP) effectively controlled the scope of a catch-all subcategory of “Other Reasons” justifying sentence reductions. The BOP used this authority almost exclusively for people who were in the final stages of terminal illness. The First Step Act of 2018 (FSA) amended § 3582(c) in a manner that freed federal judges to decide for themselves what types of circumstances meet the “extraordinary and compelling reasons” standard. The FSA also authorized people in federal custody to file motions on their own behalf, instead of permitting only the Director of the BOP to do so. Roughly a year later, the COVID-19 pandemic prompted the increased use of lockdowns and other restrictions inside U.S. prisons. Among the many thousands of people who moved for sentence reductions, several hundred argued that imprisonment with these new restrictions amounted to a greater punishment than pre-pandemic imprisonment. This Article explores the lessons that the decisions adjudicating these motions offer for the design of sentencing laws—including second looks—as well as efforts to increase transparency surrounding life inside prisons.