This paper demonstrates the techniques used by five Syriac writers of the mid-fourth to early sixth centuries in interpreting the dominical injunction in Matt 18:3 to become like children in order to enter the kingdom of Heaven. Unlike modern critical approaches, early Syriac exegesis of this saying is shaped less by the surrounding context than by association with other scriptural texts, in a manner more reminiscent of Jewish midrashic technique. The writers are Aphrahat, Ephrem, the author of the Book of Steps, Narsai and Jacob of Serugh. This study notes the interaction in some of the sources with their interpretation of Gen 2–3 and demonstrates the influence of the writers' pre-existing protology and eschatology on their exegesis of the New Testament passage. Recurring themes include whether Adam and Eve were believed to be children before the fall; whether the goal of the believer should be a return to a state of prelapsarian innocence; the existence of sexuality before the fall; and how to imitate angels as well as children. Key terms used in the sources are ̆sabrutā ‘infancy’ or ‘naivety’, and gmirutā ‘perfection’ or ‘maturity’, and the rather different concepts they represent in the five writers.