Our understanding of the structural factors shaping the agency of penal voluntary organisations in different jurisdictions is limited. This article explores how political, economic, and ideological factors in the voluntary and criminal justice sectors have affected two voluntary and community organisations (VCOs) which work with offenders – Finland’s KRITS and New Zealand’s NZPARS – and their ability to pursue their charitable goals and values. Based on qualitative thematic documentary analysis, our findings indicate that while marketisation and the populist penal policy environment contributed to the downfall of NZPARS, KRITS has been able to pursue its value-based mission of introducing unique elements to the criminal justice system, in spite of also experiencing pressures ofmarketisation. By contrasting these accounts it is clear that the current structures in New Zealand society have not supported the autonomy of all penal voluntary sector organisations, adding to the challenges of reforming the criminal justice system.