His father and mother died within a year of one another and Peter Winkel, his former schoolmaster at Gouda, became Erasmus's guardian. Erasmus was poor, but had decidedly humanistic interests. A monastery seemed to be the only place where he could pursue them, although Erasmus himself wanted to go to a university. The compromise effected was that he should go to 'sHertogenbosch (1484-7) where lived with the Brethren of the Common Life but received from them very little help in his studies. In 1487 he entered the priory of the Augustinian Canons at Steyn at the same time as his elder brother Peter went to the monastery of Sion at Delft.

In the monastery Erasmus pursued his studies, and wrote two treatises. One was on the contempt of the world, a subject which attracted several Parisian humanists who entered contemplative monasteries at about the same time, and which was not without humanist overtones, since the peace required for contemplation was also that which favoured study. The other treatise was the Anti-Barbari (Against the Barbarians). Both were humanist works in their original texts, although they were not to be published until 1521 and 1520 in texts which had later been re-written. About I492 Erasmus entered the service of Henry of Bergen, Bishop of Cambrai, by whom he was ordained priest in that year and whom he hoped to accompany to Italy.