The Citadel of Senigallia, also known as "Roveresca", was built in the early modern era starting from a defensive structure dating back to Roman antiquity. This essay focuses on the unpublished construction project by Luciano Laurana (1478-1479), and then the transition to the variant conceived by Baccio Pontelli (1480), thus resulting in a deep historical and technical investigation on the iconographic design of Italian military architecture in the sixteenth century.