This essay argues that while fostering individual and collaborative literacy can indeed promote self-awareness, confidence, and political awareness, the threat of emotional and material retribution is ever-present in jail, making the development of infrastructure challenging. Such reality compels engaged teacher-researchers to develop tactical methods for promoting literacy with limited social and material support from institutions that are primarily invested in compliant behavior. Rather than relying upon traditional models for building engaged university-community infrastructure in such contexts, I suggest a participatory curatorial model and explore the notion of curating a program within an ever-shifting set of artists, regulations, allegiances, and expectations.