This article analyzes the relationship between the sixteenth-century poet Luis Barahona de Soto and the ducal House of Osuna. Literary scholars have largely ignored the biography of Barahona de Soto, which could be further explored by researching the historical context in which the poet lived and incorporating the most recently published historical evidence. In the last decades, the analysis of patronage relationships has shown to be a rich source of knowledge in literary studies. This paper aims to fill that void in Barahona studies by discussing the relationship between Barahona and the dukes of Osuna. This relationship is mentioned often by scholars but virtually has never been studied. The article argues that Barahona benefited considerably from that relationship and could live comfortably without struggling as much as other contemporary writers -e.g., Miguel de Cervantes- did. However, the support of the dukes of Osuna was not enough to help Barahona develop a more successful literary career and publish its extensive poetic work.