The fallout of criminal convictions permeates nearly every aspect of an individual’s life long after sentences have been served and court files have been closed. This truth appears to contradict our popular beliefs that people are free to move forward with their lives after they’ve “done their time” and “paid their debt to society.” But too often people find it extremely difficult to extricate themselves from the collateral consequences of their convictions and reintegrate back into the community. Employment rights and voting rights are strongly linked to collateral consequences. These two fundamental facets of life, work and political participation, are foreclosed to millions of people because of their criminal histories. Criminal record expungements have the potential to ameliorate the impact of collateral consequences, but even these remedies should be bolstered. This Article challenges the legitimacy of collateral consequences of convictions insofar as they are illogical, purely punitive, or counterintuitive given our expectation that people achieve meaningful reintegration. The Article further implores us to analyze these challenges within a larger social, political, and historical landscape.