This chapter analyses and compares the challenges faced by the Danish, Finnish, and Swedish penal voluntary sector organisations (PVSOs). Our data indicates that the main challenges across the three Nordic countries relate to precarious funding structures and disorganised co-operation with the prison and probation services. Furthermore, the Nordic PVSOs are subjected to many similar constraints regarding their independence and critical voice as noted in previous Anglophone research. We argue that neoliberal transformations have increased the importance of Nordic PVSOs and placed them in a sense in a position of a shadow state. We also suggest that the PVSOs’ unstable position compromises prisoners’ and released prisoners’ access to welfare rights and jeopardises their possibilities for successful reintegration.