Drawing on governmentality studies and utilizing aspects of institutional ethnography, this chapter examines work in the Penal Voluntary Sector (PVS) in the youth justice system of Ontario, Canada. This chapter explores how those in helping professions working in the PVS navigate the currently preferred risk discourses and cognitive behavioral therapies in their work with youth offenders. The author traces the history of the voluntary sector in shaping the Canadian youth justice system and provides contextual considerations for understanding the current youth justice system and the role of the PVS. The PVS workers who were interviewed do not experience their work as autonomous from the state. Instead, PVS work is conducted in relation and in reference to the traditional criminal justice system. Within these social relations, PVS workers resist, accommodate, subvert, extend, and negotiate state goals and rationalities.