Even as education is always a high-stakes endeavor, the stakes of prison education contexts are even higher. Given the ongoing violences of surveillance, censorship, and obfuscation in prisons, these environments are neither conducive to literacy practices nor do they support the flourishing of human life or growth. Simultaneously, however, prison educators working with incarcerated students navigate and push back against these oppressions to support students learning in everyday contexts. In exploring these tensions through qualitative research, I argue that prison educators mobilize complex and highly situated literacy practices to subtly and quietly bend the rules in carceral environments. In deploying subversive acts of “creative maladjustment” (King Jr., Kohl), these instructors circumnavigate state power to sustain educational commitments to incarcerated students in the face of state violence. Through such explorations, I contend that literacy educators can better comprehend what it means to resist the state: for research, praxis, and survival.