כִּֽי־גֹאֲלָ֥ם חָזָ֑ק הֽוּא־יָרִ֖יב אֶת־רִיבָ֣ם אִתָּֽךְ׃
װאָרום זײער אױסלײזער איז שטאַרק, ער װעט זיך אָננעמען זײער קריג אַקעגן דיר.
Mishneh Torah, Human Dispositions
A man is obliged to watch out for orphans and widows, for their soul is very lowly, and their spirit humble even though they be wealthy in money, even though they be the widow and orphans of a king, we are charged concerning them, for it is said: "Ye shall not afflict any widow or fatherless child" (Ex. 22.22.). What, then, are the rules of conduct toward them? One must not speak to them save in soft words; not to treat them in any way, save in an honorable way; not to pain their body with labor, nor their heart with hard words; to be careful with their money more than with the money of one's own self. He who worries them, or vexes them, or pains them, or masters them, or causes the loss of their money, violates a prohibitive commandment, needless to mention one who smites them or curses them. This prohibitive commandment, notwithstanding that the punishment of flogging is not inflicted for its violation, behold, the punishment therefor is plainly stated in the Torah: "My wrath shall wax hot, and I will kill you with the sword" (Ibid. 22.23). Moreover, He Who spoke and called the universe into being, made a covenant with them, that whenever they will cry out against violence, they shall be answered, even as it is said: "For if they cry at all unto Me, I will surely hear their cry" (Ibid. 22.22). But all these warnings are applicable when one afflicts them out of a selfish motive; but if the master who, in order to instruct them in the Torah, or teach them a trade, or lead them in a righteous path, does inflict punishment upon them when they are contrary, behold, such he may do. Nevertheless, he should not follow the rules of other people in dealing with them but conduct himself toward them differently, to lead them slowly, with great mercy and honorable consideration, even as it is said: "For the Lord will plead their cause" (Prov. 22.23). Whether it be a fatherless orphan or a motherless orphan, the treatment to be accorded to them must be identical. Now, until when are such called orphans for the purpose of the subject treated herein? Until they will have no need to lean upon a grown-up person to rear them and support them, but each one be able to take care of all his personal needs even as all other adults do.
Kitzur Shulchan Arukh
You should be very careful [in the way you treat] orphans and widows, to speak only kindly to them, to treat them respectfully, not to hurt them even with words,59This prohibition includes taunting widows and orphans, causing them anger, wounding their feelings, oppressing them, and causing them financial loss. because their souls are very depressed and their spirits are low, even if they are wealthy. Even [regarding] the widow and the orphans of a king, we are warned [in the Torah], for it is said: "Do not mistreat a widow or an orphan."60Exodus 22:21. A covenant was made [with widows and orphans] by Him Whose Word called the world into being, that whenever they cry because of an injustice that was done to them, their [cries] will be answered, for it is said: "For if he cries out to Me I will hear his cry."61Ibid. 22:22. This applies only where someone hurts them for his own benefit. But if a teacher afflicts them in order to teach them Torah or a trade, or to lead them on a straight path, this is permitted. Nevertheless, [the teacher] should be careful to guide them gently and with great compassion, for it is said: "For God will plead their cause."62Proverbs 23:11. [In all of these laws, it makes no difference] whether he is an orphan from his father or an orphan from his mother. And for how long are they considered orphans in this regard? Until they are able to take care of all their needs by themselves as all other adults.