Be on guard against her impudent eye: Good News Translation focuses on the attitude behind the impudent eye and says “is too self-willed.” For the whole line we could say “When she has a defiant look [in her eyes], be on guard” or “… be very careful.”

And do not wonder if she sins against you: Here wonder means “be surprised.” The verb sins does not adequately express the Greek verb here. Its basic meaning is to hit a wrong note in music; here it seems to have the meaning “go wrong,” but going wrong with reference to the father. Good News Translation “disappoints” is a good translation, true to the nuance of the Greek verb and true to the context.

Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on Sirach. (UBS Helps for Translators). New York: UBS, 2008. For this and other handbooks for translators see here.