In the absence of a critique of the logics at the heart of the prison industrial complex, seemingly progressive trends such as prisoner reentry initiatives will simply bolster racialized state violence. This essay grapples with questions of representation and power, and details how the disposability of imprisoned people is reproduced and renaturalized through carceral practices. Academic accounts continue to be complicit in this process, without a complex theorizing of subjectivity, representation, and state violence. This essay uses interviews with formerly imprisoned people in the Twin Cities to disrupt the way that formerly imprisoned people’s narratives are “mined as rich sources” in pathologizing and voyeuristic ways. Prisoner reentry programs appear progressive on the surface; however, they expand the prison industrial complex through perplexing logics that make it harder for women to navigate toward freedom. I use the notion of perplexity as a rubric for understanding penal logics and subjectivities as they emerged in my interviews with people recently released from Minnesota’s only women’s prison and analyze how they reproduce the vulnerability of people leaving prison. The gender-responsive façade of this unique prison and the surveillance orientation of reentry programs naturalized imprisonment as a solution to social problems in deeply problematic ways.