This article reconstructs the cultural, familial and religious environment in which Sofonisba Anguissola’s training took shape, highlighting her role among the leading portraitists of the sixteenth century and her early recognition within the “Europe of the courts”. Drawing on archival sources, literary testimonies and stylistic analysis, the study examines portraits of ecclesiastical figures attributable to her early Cremonese period, with particular attention to the Portrait of a Lateran Canon recently acquired by the Nationalmuseum in Stockholm. The paper critically reassesses the identification of the sitters, relating them to the milieu of the canons of San Pietro al Po and to local patronage networks. These works are shown to reflect strategies of familial self-representation, aristocratic dynamics and the religious tensions of sixteenth-century Cremona, offering a new documentary and historical reading of the painter’s early activity.