Chapter 2 treats the early Italianate-poetry that Cervantes wrote for Isabel de Valois (1567, 1568) when he was around twenty years old as serious works composed within the particular cultural and poetic practices of the Habsburg court. In his first sonnet, Cervantes’ speaker develops a conceptual play between the speaking ingenio and the lofty lady through the use of an exalted apostrophe, a key feature of Pastoral Petrarchism that would inflect the subsequent decades of the author’s literary career. The only known copy of this sonnet was preserved in an early seventeenth-century manuscript collection of pastoral and erotic lyric and narrative poetry pertaining to the Habsburg court, now housed in the Bibliothèque Nationale de France, Richelieu. This chapter examines and draws upon the manuscript in order to reconstruct the literary environment in which Cervantes wrote, as it was understood by the early modern compiler (a primary source on readership, reception, and genre). Ms. Espagnole 373 also recontextualizes the poetry that Cervantes composed the following year for the untimely death of Isabel on October 3, 1568. This chapter considers Cervantes’ relationship to Giulio Acquaviva while the papal legate was present in the Habsburg court, his journey to Rome, and the Sigura affair.