While scholarship has often treated Sir 15:11–20 primarily within a philological and exegetical framework, this book examines the passage through a text-critical, comparative, and reception exegetical analysis. The study begins by situating Ben Sira within the international context of wisdom literature in Hellenistic times and reviews the previous research. It then offers a text-critical analysis of this passage, assessing textual variants and translation choices. This is followed by a comparative analysis of key texts in Ben Sira, which situates the teaching of free will in 15:11–20 within the context of the larger structure of the book. The comparison helps to clarify the passage’s meaning within a system of related doctrines, themes, and anthropological terms. The study continues with an examination of the history of exegesis, specifically addressing how Augustine, Aquinas, Erasmus, and Luther interpreted this passage. The results of this research suggest that Sir 15:11–20 presents human responsibility within the interplay between freedom and grace. This study also contributes to the ongoing conversation among scholars regarding the value of combining historical-critical methods with reception exegesis.