הלכה על יבמות 130:20

This applies only in a case when you [have reason to] believe that the sinner will listen to you,⁴⁹If the sinner is your friend you should chide him even if you know that he will pay no attention to your words. (Magein Avraham 156:2) but when you know [for sure] that he will not pay attention to your words, then you are forbidden to admonish him. For Rabbi Ila'a said in the name of Rabbi Elazar ben Rabbi Shimon,⁵⁰Yevamos 65b. "Just as it is a mitzvah for a person to say something that will be heeded, so it is a mitzvah to refrain from saying something that will not be heeded." Rabbi Abba says, "It is his duty" [to refrain from saying anything that will not be taken under consideration]. for it is said:⁵¹Proverbs 9:8. "Do not admonish a scorner lest he hate you; reprove a wise man and he will love you."

That is that He commanded us to be fruitful and multiply, with the intention of preserving the species. And that is the commandment of piryah verivyah. And that is His, may He be exalted, saying, "And you, be fruitful and multiply" (Genesis 9:7). And they have already explained (Berakhot 16a) that a groom is exempt from the recitation of Shema on account of being busy with [this] commandment. And the laws of this commandment have already been explained in Chapter 7 of Yevamot. But women are not obligated in this commandment. And in the explanation, they said (Yevamot 65b), "A man is commanded to be fruitful and multiply, but not a woman." (See Parashat Bereishit; Mishneh Torah, Marriage 15.)

From the laws of the commandment is that which they, may their memory be blessed, said (Arakhin 16b) that the obligation of this commandment is until hitting - meaning to say that the one rebuking is obligated to multiply his rebukes upon the sinner until it is enough that the sinner is close to hitting the one rebuking. And nonetheless they, may their memory be blessed, also said (Arakhin 16b) that if the one rebuking sees that there is no benefit at all found from the words of his rebukes - from the greatness of the sinner's evil, or that he is deaf [to it] and extremely evil and [the rebuker] is afraid of him that he not stand against him and kill him - that he is not obligated in this commandment with this man. And this is what they, may their memory be blessed, said (Yevamot 65b), "In the same way as it is a commandment to say something that will be heard, so [too,] is it a commandment to be quiet in a place where the thing will not be heard" - since there would be disgrace in the matter for the one who is rebuking and no benefit to the one who is rebuked. And nonetheless, it is for every careful person to consider and to pay great attention to these matters and to think and see if there will be a benefit to the sinner with his words, such that he should rebuke him and trust in God, may He be blessed - as He will help him in his fight with His enemies. And let his heart not be soft and let him not fear, since 'the Lord protects all those that love Him and He obliterates all of the evildoers.' And if the sinner returns, he will have great reward for this. But the one who has in his hand [the possibility of] bringing him back and rebuking him, and does not rebuke him, is caught in his sin. And this is something clear from the words of our Rabbis (Shabbat 55a) and also from Scripture (Isaiah 3:14). And they, may their memory be blessed, also said (Yevamot 65b) that even a minor is obligated to rebuke an adult if he sees the adult going in a path that is not good. [These] and the rest of the details of the commandment are elucidated in scattered [places] in the Talmud (see Mishneh Torah, Laws of Human Dispositions 6).