In addition to his signal achievements as a knight errant, Don Quixote de la Mancha produced a small but noteworthy body of poetry. Samples of this poetry appear at different places in the history that Miguel de Cervantes wrote about the great knight. The most dramatic depiction of Don Quixote as a poet comes in chapter 26 of the first half of the story, when Don Quixote retires to the mountains to lament his love for the beautiful Dulcinea del Toboso. He sends his squire, Sancho Panza, on a mission to Dulcinea to express his love. Then Don Quixote strips down to his underwear, leaps about a bit, and writes some poetry. I want to consider here the challenges he faces in his poetic undertaking.