This paper calls attention to educational opportunities inside of correctional facilities. Literature correlates a direct relationship between education and reduced recidivism (Esperian, 2010; Rand Corp., 2014; DOJ, 2016b). Using Freire and hooks’ educational philosophies I discuss how I engaged critical pedagogy while teaching incarcerated juvenile offenders. I found that the youth I worked with were eager for an educational experience that allowed them to critically engage with our social world and analyze their lived experiences. Teaching in this controlled environment was challenging. My autonomy was encroached upon, which offered me a unique insight into the daily lives of the inmates. Through dialogical interactions, my perceptions and assumptions about incarcerated youth were confronted and changed. A radical and transformative pedagogy created a space where the notion of freedom could be negotiated.