This paper examines the prison poetry (habsiyyat) of young al-Mutanabbi (d. 965), one of the most celebrated poets in Arabic literature. Imprisoned for offending sensibilities, al-Mutanabbi responded with a series of poems that earned his release. Despite the outstanding reception of al-Mutanabbi by commentators and literary critics, no study has offered an interpretation of these poems. My analysis of his overlooked habsiyyat engages current theories of power relations by demonstrating how art effects change. This paper aims to highlight the unexpected ways that medieval artists not only communicated unspeakable experiences, but also achieved great feats. The young al-Mutanabbi's time in prison resulted in poetry that reportedly prompted the governor to grant his freedom. My analysis of his habsiyyat, alongside some examples of prison poetry from other historical contexts, demonstrates how poets transform pain into verbal art in order to effect change. In al-Mutanabbi's case, the poetic skills that he honed in prison would prepare him for a lifetime of poetry that would express emotions, effect change, and come to occupy a prominent position in the Arabic literary canon. I approach al-Mutanabbi's prison poetry by using methods from comparative works on torture (Elaine Scarry) as well as a performance theory (Richard Bauman), which give attention to composition strategies, interactions between artist and audience, and the retransmission of poetry beyond its debut context. By using performance theory and comparative studies on torture, I illustrate how unspeakable pain can be expressed through poetry and that artists advocated for themselves in the face of political authority in the Middle Ages. This analysis affords comparisons with contemporary literature, bridging the perceived gap between classical and modern literature. This project adds one medieval case study to the body of literary criticism of prison literature that focuses almost exclusively on resistance to late twentieth-century violence. This paper exposes the relevance of al-Mutanabbi's prison poetry to contemporary experience and to current literary studies. The outcome of this study will be a published article.