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This paper focuses on the role of emotions in critical pedagogy, specifically in the context of prison education. It centers on the pedagogy of love, the foundation and emotional source of critical pedagogy and aims to discuss the following question: how do educators address the pain incarcerated students experience in liberatory education? In the context of prison education, pain and trauma fill students’ lives, and educators’ love is necessary to co-create spaces of safe discomfort. Through the pedagogy of love, the pedagogy of healing and pain, and the concepts of difficult knowledge and troubled knowledge, I discuss how the pedagogy of discomfort becomes the center of prison education.