The last decade has seen the beginning of a new era in United States criminal justice policy, one characterized by a waning commitment to over-criminalization, mass incarceration, and a punitive War on Drugs as well as a growing regret for the consequences of our prior policies. One of the central questions raised by this shifting paradigm is what to do about the millions of individuals punished, marked, and shunned as a result of policies we now regret. This issue is particularly pointed for marijuana convictions, as the coexistence of strict regimes of collateral consequences for drug convictions and the active government promotion of a new cannabis economy present a stark and deeply racialized contrast. This Article argues that, in states where marijuana has been legalized, our policy-making apparatus should acknowledge and move to redress both the failings of our prior system of drug regulation and the social and economic disparities in current law by embracing a concept of “retroactive legality.” Retroactive legality is a framework in which we seek to restore those convicted of marijuana crimes to the rights and civic status they would have had if their conduct had never been illegal. Such an approach would build upon the piecemeal expungement and pardon policies adopted or proposed in some of these jurisdictions but would reach substantially further, by incorporating those convicted of more serious offenses, putting the onus on the state to identify and clear such convictions, and declining to impose additional requirements and costs on those seeking to have their convictions retroactively legalized.