Religion has played an important role in the movements of merchants, settlers and officials of the trading companies between Europe and 17th-century America, either by urging to depart or by ensuring transnational settlers with a cultural fixation through the adoption of a new religious identity. In this article, the contrasting religious destinies of three important actors of early 17th-century New Netherland are examined. They embody three ways of confessionalisation, with different degrees of intensity: the first comforter of the sick Bastiaen Jansz Krol, a former Mennonite, who during a short moment acted also as director of the colony; the second Reformed minister Evert Willemsz Bogaert (Bogardus), educated in a Puritan climate, but who, pushed by the evolution of the colony, was to adopt a critical stance toward confessionalisation; and the merchant Govert Loockermans, born in a Catholic family of Spanish Brabant, but converted into an exemplary Protestant burgher and dignitary in New Netherland.