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Budget cuts have led to reduced expenditures on beneficial prison programming. Despite evidence that educational programs have important rehabilitative effects, such programs have also suffered significant reductions. Programs that have not been eliminated have increasingly relied on volunteers. Prison accreditors demand that inmates be given the opportunity to participate in post-secondary education. Finding funds for such programming, however, is particularly challenging due to budget constraints. One might therefore expect that prison administrators would enthusiastically welcome professors willing to volunteer their services. In practice, however, volunteers from the academy are often viewed with suspicion. This paper details the process of establishing college courses at a women’s prison in Pennsylvania, and the different and sometimes contradictory reactions of prison administrators, inmates, student and professorial participants. The navigation and negotiation between these groups has not run smoothly. This experience reveals that prison administrators may not view college professors and students as ideal volunteers. The paper concludes with recommendations for how best to navigate the terrain to provide educational programming to the incarcerated.