By the end of the thirteenth century, the communes of central and northern Italy decided to entrust their initiatives of information gathering and of espionage to specific institutions. Receiving different names in various cities, from the Florentine Deputati super Spiis to the Bolognese Officium Spiarum, these structures were a constant topic of council discussions. Many a council minute, in cities where the Papacy exercised a strong influence, report that in particularly delicate cases the Pope was consulted and interfered in the practices of these institutions. The aim of this project is to explore these episodes—often only vaguely described in communal sources—by systematically reading the papal correspondence produced by four specific popes, chosen for their temporal proximity to the functioning period of these offices: Clement V (1305–14), John XXII (1316–34), Benedict XII (1334–42), and Clement VI (1342–52). The broader goal is to understand how much this papal interference shaped, altered, and influenced these institutions, and how it marked the form these cities gathered information and practiced espionage in general.