Prison poems, texts written in conditions of physical captivity or on the subject of imprisonment, flourished in the fifteenth century. This edition compiles five such poems, all of which draw on Boethius’s Consolation of Philosophy, the sixth-century philosophical treatise that preached against fickle Fortune and for the constancy of God. James I of Scotland and Charles D’Orleans—both royalty captured by political rivals—follow a Boethian trajectory in their poems (the Older Scots Kingis Quair and Middle English Fortunes Stabilnes, respectively), though they situate themselves as prisoners to love. George Ashby, a government clerk imprisoned for an unknown reason, pleads in his Complaint of a Prisoner in the Fleet 1463 for patience and purification of the soul against the vicissitudes of Fortune. Taken together, these poems consider prison not only as a physical condition but also as a literary trope that allows for both complaint and empowerment, providing avenues for escape through the pursuit of love, religious faith, or intellectual contemplation.