Several years ago, I was asked to prepare a commentary on Ben Sira from a Jewish perspective, one that took seriously the connections between the book and later rabbinic writings. There was already a commentary that went in this direction, but it was only in Hebrew. As I was working on this commentary I published a short (and accessible) article called, “The Wisdom of Ben Sira: How Jewish?“
That commentary is finally out, as part of The Jewish Annotated Apocrypha, edited by Jonathan Klawans and Lawrence Wills (Oxford University Press, 2020, pp. 427-498). I am now using the volume for an adult education course, and for those considering doing such a thing, it teaches very well. I am very grateful to the editors for their work on this volume, and helping me to improve my own contribution.
I spent several good years getting to know Ben Sira. He’s definitely worth a look!