The Greek version of Sirach has been neglected, probably owing to its complex textual history and its appearance in the Apocrypha (a rare exception is the work of B.G. Wright). Its translation technique has also often been viewed as displaying a high degree of interference from the Hebrew and therefore unsophisticated. However, the translator himself uniquely provides a preface to the translation, displaying literary concerns and awareness of translation issues. Attention to linguistic features in the translation indicates a trend towards natural Greek construction, and vocabulary of a literary nature. This paper will therefore argue that this is an important step in the development of translation methods among Greek-speaking Jews. Drawing examples from key passages of the book it will show how the translation has crafted the translation around key Greek literary themes, and while still naturally following the Hebrew source text he has expressed the message in Greek terms. In that way the translation it itself a negotiation between Greek and Hebrew cultural worlds. It reflects the work of an accomplished translator and skilled Greek writer, and suggests a development and reconsideraion among Jews of methods in translation. It therefore serves as a window into the cultural world of Jews in Egypt.