Late medieval culture tends to value pain highly and positively. Accordingly, much medievalist scholarship links pain with fear and emphasizes their usefulness in the period’s philosophy, literature, visual art, and drama. Yet, key moments in The York Play of the Crucifixion, The Second Shepherds’ Play, and The Tretise of Miraclis Pleyinge trouble the significance of pain and its relationships with punishment and performance; these works admit the unreliability of pain and fear, even as they harness the formidable power pain holds throughout Middle English literature. This essay analyzes passages from all three texts to demonstrate their deep skepticism about the signifying power of pain alongside their abiding investments in pain’s utility. I argue that these texts ultimately challenge Middle English drama’s dominant discourses of patriarchy and empire by way of their representations of pain.