This article examines the dedicatory letters to Henry Wotton of two books published in Italy : Fonti toscani by Orazio Lombardelli (Siena 1598) and Morte innamorata by Fabio Glissenti (Venice 1608). Wotton came into contact with Lombardelli during his first Italian journey of 1591-1593. The volume dedicated to him describes the readings he probably did under Lombardelli’s guidance to learn Italian during his stay in Siena. The dedication of Glissenti’s Morte innamorata to Wotton, the Protestant ambassador of a heretic king, sparked controversy and protest from the Inquisitor, the Nuncio, and the Curia of Rome. The reconstruction of these controversies adds to our understanding of what has been defined as the philo-Protestant period in Venice (1606-1609).