Financial austerity, welfare state retrenchment, and the movement towards evidence-based interventions have intensified the pressures on penal voluntary sector (PVS) organizations. The result is an increasingly competitive field of social service provision in which organizations must differentiate themselves in the struggle over funding, contracts, symbolic authority, and potential clients. We explore this struggle by examining the distinct roads to reentry constructed at four PVS organizations in Ontario, Canada. Our analysis initiates a dialogue between individual narratives and organizational discourses, contending that the road to reentry is coauthored among organizations and criminalized individuals—albeit on unequal terms. Our findings reveal that there are significant pressures for criminalized individuals to perform narrative labor to align themselves with organizational understandings of reentry. Such pressures include: the denial of services or social assistance payments, threats of being returned to prison for “inadequate” participation in rehabilitation, and risks of not being considered for coveted “professional ex” positions at PVS organizations. In light of these empirical findings, we also offer a conceptual reflection on the challenges criminalized individuals likely face accessing services from multiple organizations with differing roads to reentry, suggesting that navigating these diverse roads not only requires narrative labor, but also narrative dexterity.