Reversing the tough-on-crime policies that have defined American criminal justice for the past two decades, cash-strapped states across the nation have begun reducing the number of people they confine in prisons and jails. In their efforts to reduce correctional populations, numerous states have passed laws that allow parole boards, prison officials, or judges to shorten the sentences of people already serving time in custody. These so-called "early release" laws have proven highly controversial, and in at least three states have been repealed outright. In others, they remain on the books but have provided less savings than anticipated because of the failure of decision-makers to utilize their newly-conferred authority. This Article examines the early demise of early release in several jurisdictions, identifying practical, political, and moral obstacles to the practice of early release that may account for the failure of recent legislation. Responding to those concerns, I suggest principles to guide future efforts to reduce custodial populations through the use of early release. These include drafting laws that respect the limits of institutional capacity, adopting principled rules about who may be released early and for what reasons, and emphasizing the moral concerns that justify efforts to reduce prison populations.