Efforts to assist in the reintegration of prisoners back into society are typically either risk-based or need-based. An alternative philosophy for reintegration, strengths-based (or ‘restorative’) reentry, treats people returning from prison as assets to be utilized rather than threats. This chapter explores the theory behind these efforts, drawing on one of the original formulations of this perspective in the work of the psychologist Albert Eglash. Eglash argues that the process of redemption requires more than just punishment or providing compensation to one’s victims, but involves individuals going a ‘second mile.’ This ‘second mile,’ which he calls ‘creative restitution’ involves making up for one’s wrong-doing by working to help others, in particular other prisoners or those at risk of going to prison. We argue that these strengths-based efforts work primarily as a stigma management strategy. Individuals who have been punished for doing wrong can redeem their reputations through explicit involvement in help-giving behaviors and other efforts to contribute positively to society. This change in public perceptions can then lead to changes in the person’s own self-beliefs and self-identity. We conclude by exploring a new development in the strengths-based movement, which we describe as going a ‘third mile.’ This involves more direct efforts at stigma reduction through activism on ex-prisoner issues on a political level. We argue that this is a natural next step in efforts towards destigmatization.