Le Lévitique 19:10 Commentaire : Rashi, Kitzur Ba'al HaTurim, Rashbam & Rabbeinu Bahya

לא תעולל AND THOU SHALT NOT GLEAN [THY VINE YARD] — (עלל is a verb connected with the noun עולל "young, tender, not developed"; cf. Samuel 15:3: עולל ויונק) thus לא תעולל means, thou shalt not take the tender grapes of it. They can be recognized as such from the description given in Mishna Peah 7:4 (cf. also Sifra, Kedoshim, Chapter 3 3) where it is stated: What are עוללות? Clusters which have neither כתף, “arms" nor נטף, "drippings".

You shall not gather. The commandment, “you shall not steal,” is juxtaposed to this to warn a property owner not to steal from what is fitting for the poor, and also to warn the poor not to steal from the property owner more than what they are entitled.

לא תעולל, meaning something akin to the concept of peyah in cornfields, i.e. the farmer must not harvest the entire vineyard for his own use. The parallel verse appears in Jeremiah 6,9 עולל יעוללו כגפן, “let them glean over and over, as a vine.”

ופרט כרמך [NEITHER SHALT THOU COLLECT] THE FALLEN GRAPES OF THY VINE YARD — i. e. the single berries of the grapes which fall to the ground during the grape gathering.