This study considers ethical questions of freedom and reconciliation in Jimmy Boyle’s autobiographical A Sense of Freedom (2016). A Scottish life prisoner, Boyle describes a moral phenomenology of freedom and reconciliation through his life and his time in prisons, including Glasgow’s Barlinnie Special Unit. Promoting mature democratic relations between prisoners and staff, the Unit enabled development and change in participants’ moral psychology. Boyle’s ‘sense of freedom’ moves from negative forms of refusal, resistance and withdrawal to ever more positive forms: abstract ideal freedom, emancipatory agency, trust, collective empowerment, taking responsibility, coming alive and loving creativity. Reconciliation recognised the human in the enemy, mature engagement, democratic involvement and thinking socially and politically beyond the prison. This metaphysics transcending violence was grounded in Boyle’s metapsychology as one capable of love. The chapter draws on earlier discussions of freedom and reconciliation in the young Hegel, recognition and complex victimhood, atonement and mature retributivism. The penal system is seen as combining a persecutory impulse in the major key and humanistic traces in the minor, a ‘structure in dominance’ of the former over the latter. Barlinnie Special Unit inverted this structure briefly, pointing to a deep abolitionist tendency inside what became ‘the loving prison’.