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This paper focuses on the fascinating figure of Leonor Pimentel, daughter of the Marquises of Távara and lady-in-waiting to Queen Margaret of Austria (r. 1598-1611) and Queen Isabel of Bourbon (r. 1621-1644). In 1622, Leonor married the Count of Benavente, Isabel of Bourbon’s High Steward and an important political figure in Philip IV’s new government. Due to her privileged position at the Spanish Court and her connections to Florence, Leonor acted as agent for the Grand Duchesses of Tuscany, Cristina of Lorena and Maria Maddalena of Austria. She provided them information about the different court factions, acted as cultural intermediate between the Grand Duchesses and the Spanish Royal family, and supported Tuscan political interests. In return, she obtained Florentine gifts and benefits for herself and for the members of her family network.