Commentary for Deuteronomy 23:16

לא תסגיר עבד THOU SHALT NOT DELIVER [UNTO HIS LORD] THE SERVANT [WHO IS ESCAPED FROM HIS LORD UNTO THEE] — Understand this as the Targum has it: עבד עממין the servant of the heathens. Another explanation is: that it implies even a Canaanite servant belonging to an Israelite who fled from outside the Land (from a foreign country) into the Land of Israel (Gittin 45a).

THOU SHALT NOT DELIVER UNTO HIS MASTER A BONDMAN THAT IS ESCAPED. This is connected with the section above that [when you go forth against the enemy] if a slave flees from his master against whom the host has gone forth and saves himself by fleeing to your camp you are not to deliver him to his master for money that he may give you. And since it states, he shall dwell with thee, in the midst of thee, in the place which he shall choose,²⁸⁴Verse 17. it appears that it is a commandment that he become a free man and that we should not enslave him. The reason for this commandment is that with us he will worship G-d and it is not proper that we return him to his master to worship idols. Moreover, it is possible that he [the bondman] may show them the entrance into the city,²⁸⁵Judges 1:25. for in that way they will capture many cities through slaves and captives fleeing from there. And our Rabbis have said²⁸⁶Gittin 45a. [that this prohibition is applicable] even [to] a Canaanite bondman who belongs to an Israelite who fled from outside the Land into the Land of Israel, for this one too, should preferably work for those who dwell in the Land of G-d and be saved from working for those that dwell in an unclean land,²⁸⁷Amos 7:17. and where not all commandments are binding.

לא תסגיר עבד אל אדוניו, after the Torah had spoken of the sanctity that must be prevalent in an encampment of Jewish soldiers in war, it switches to matters which are apt to happen in such surroundings, explaining how to correct deviations. One of these is how to deal with a gentile slave who has escaped from his master and taken asylum among the Jewish people; another is the subject of loose women who have infiltrated into the encampment of the Jewish army, an everyday occurrence in gentile armies. (verse 18)