The extreme complexity of Sirach’s text at times makes it almost impossible to come to one clear conclusion as regards certain issues. There are numerous differences between various translations of this deuterocanonical text. In addition, the Armenian translation, being a textual witness to not one but multiple parent texts, has its own complications. This research provides a sustained theological reading of the Armenian text of Sirach on the basis of Yakob Nalean’s commentary written in the 18th century. At the same time it places a great emphasis on the textual evaluation of the various versions of Sirach in Armenian. In this respect an attempt has been made to display the unique features of the Armenian Sirach within the wider scope of the scholarship of this biblical text. Through a comprehensive linguistic and theological analysis of some major parts of Sirach in Armenian, this study assesses the extent to which this book was in use amongst Armenians throughout the centuries. In particular, the numerous references to Sirach in both Armenian and non-Armenian patristic literature are examined, with the aim of dating the first translations into Armenian and tracing the development of the text in the Armenian medieval schools.