This chapter presents the significance of both Spanish cancioneros and Portuguese cancioneiros for the scholarly examination of medieval Jewish history and literature on the Iberian Peninsula. Through a close integration of historiographical and literary analysis, all major cancioneros are examined and contextualized based on exemplary interpretations. The chapter is divided into six parts; the first one explains the importance of the historical context of warfare in the development of late medieval Iberian cultures; the second part showcases Cancionero de Baena and Cancionero de Palacio as the two initial stepping-stones of the new poetry style and their connection with the problems endured by both Jewish and conversos; the third part explains the evolution occurred during the reign of Enrique IV (1454-1474), whilst the fourth part is focused on the Catholic Monarchs reign (1474-1504) and how the Castilian cancioneros can be considered as a real proof of the issues endured by Jewish and converso populations during those uncertain times. Finally, the fifth part analyzes the influence of the expulsion of the Jews and the Inquisition in the paramount example of Castilian poetry, the Cancionero general (1511), by Hernando del Castillo; and the sixth and final part is centered on the expulsion of the Jews from Portugal and how this is reflected on the Cancioneiro geral (1516), by Garcia de Resende.