As mass incarceration and supervision decline in the U.S., subtler forms of “invisible punishment” continue to affect individuals with a history of legal system involvement. Increasingly, the state recedes from direct involvement in invisible punishment, instead devolving responsibility—and potentially controlling at a distance—community-based organizations. In the process, punishment in the community is shaped by both the state and various segments of civil society. The present ethnography examines how staffers at a community-based reentry organization are subject to and resistant to state influence, and how this resistance generates new forms of invisible punishment. While state influence directs staffers to provide services focused on altering clients’ internal dispositions, staffers resist state influence by encouraging members to be their own advocates against the penal system. This agonistic process of resistance generates a hybridized form of invisible punishment, commingling the organizational goals and routines of penal state authorities with those of reentry staffers who see advocating against structures of punishment as a core mission. The final, hybridized form of this mode of penalty requires the client not only to look inward to effect dispositional changes, but also to look outward to be an active agent advocating against the exclusionary penal structures affecting them.