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1 When thou wilt do good know to whom thou doest it; so shalt thou be thanked for thy benefits. 2 Do good to the godly man, and thou shalt find a recompence; and if not from him, yet from the most High. 3 There can no good come to him that is always occupied in evil, nor to him that giveth no alms. 4 Give to the godly man, and help not a sinner. 5 Do well unto him that is lowly, but give not to the ungodly: hold back thy bread, and give it not unto him, lest he overmaster thee thereby: for [else] thou shalt receive twice as much evil for all the good thou shalt have done unto him. 6 For the most High hateth sinners, and will repay vengeance unto the ungodly, and keepeth them against the mighty day of their punishment. 7 Give unto the good, and help not the sinner. 8 A friend cannot be known in prosperity: and an enemy cannot be hidden in adversity. 9 In the prosperity of a man enemies will be grieved: but in his adversity even a friend will depart. 10 Never trust thine enemy: for like as iron rusteth, so is his wickedness. 11 Though he humble himself, and go crouching, yet take good heed and beware of him, and thou shalt be unto him as if thou hadst wiped a lookingglass, and thou shalt know that his rust hath not been altogether wiped away. 12 Set him not by thee, lest, when he hath overthrown thee, he stand up in thy place; neither let him sit at thy right hand, lest he seek to take thy seat, and thou at the last remember my words, and be pricked therewith. 13 Who will pity a charmer that is bitten with a serpent, or any such as come nigh wild beasts? 14 So one that goeth to a sinner, and is defiled with him in his sins, who will pity? 15 For a while he will abide with thee, but if thou begin to fall, he will not tarry. 16 An enemy speaketh sweetly with his lips, but in his heart he imagineth how to throw thee into a pit: he will weep with his eyes, but if he find opportunity, he will not be satisfied with blood. 17 If adversity come upon thee, thou shalt find him there first; and though he pretend to help thee, yet shall he undermine thee. 18 He will shake his head, and clap his hands, and whisper much, and change his countenance.
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[AD 430] Augustine of Hippo on Sirach 12:4
Execute mercy to the wicked, but not because he is wicked. Do not receive the wicked, in so far as he is wicked, that is, do not receive him because you have an inclination and love toward for his iniquity. For it is forbidden to give to a sinner and to receive sinners. Yet how do we hear, “Give to every one that asks of you,” and this, “If your enemy is hungry, feed him”? This is seemingly contradictory, but it is opened to those who knock in the name of Christ and will be clear to those who seek. “Do not help a sinner,” and, “Do not give to the ungodly,” and yet, “Give to every one who asks of you.” But it is a sinner who asks of me. Give, not as though you were giving to a sinner. When do you give as though you were giving to a sinner? When that which makes him a sinner pleases you so that his sin becomes the reason that you give.

Source: EXPOSITIONS OF THE PSALMS 102:13
[AD 604] Gregory the Dialogist on Sirach 12:5
The mind should first be predisposed to patience, and then either much or all should be given bountifully, otherwise, when the inroad of want is borne with but little equanimity, then, both the reward of previous bounty could be lost and subsequent murmuring might bring even worse ruin on the soul. Just in case they should give nothing at all to those on whom they ought to bestow something, let them hear what is written: “Give to everyone who asks of you.” And, just in case they should give something, however little, to those on whom they ought to bestow nothing at all, let them hear what is also written: “Give to the good person, and do not receive a sinner; do well to the one who is lowly, and do not give to the ungodly.” And again, “Set out your bread and wine on the burial of the just, but do not eat and drink with sinners.”6For the one who gives his bread and wine to sinners provides assistance to the wicked because they are wicked. This is also why some of the rich of this world nourish players with profuse bounties, while the poor of Christ are tormented with hunger. He, however, who gives his bread to one that is indigent, though he is a sinner, not because he is a sinner but because he is a human being, does not in truth nourish a sinner but a poor righteous person, because what he loves in him is not his sin but his nature. Those who already distribute compassionately what they possess are to be admonished also so that they might learn how to be vigilant, lest, when they redeem by alms the sins they have committed, they commit others that will still require redemption; otherwise they might suppose that the righteousness of God is for sale, thinking that if they take care to give money for their sins, they can sin with impunity.

Source: PASTORAL RULE 3:20
[AD 533] Fulgentius of Ruspe on Sirach 12:6
The impious and sinners who have no intention of repenting of their impiety or iniquity will be condemned at the end to eternal torments, while to those who have repented God will lavish his mercy. This is what is written in the book of Ecclesiasticus: “The Most High has mercy on the penitent and will inflict punishment on the impious and sinners.” Further, in the same book it is said, “Remember that wrath will not be late in coming. Humble yourself to the utmost, because fire and worms fill up the punishment of the ungodly.” Again, Isaiah says that “their fire shall not be quenched, and their worm shall not die.” It is also written in Ecclesiasticus, “A synagogue of sinners is like a bundle of oak, and their end will be the flame of fire. The way of sinners is full of offenses, and, at the end, there will be the fiery pit, darkness and pains.”

Source: ON THE FORGIVENESS OF SINS 1:27.2
[AD 407] John Chrysostom on Sirach 12:13
Like a wild beast fallen onto a noble and delicate body incapable of defending itself, thus vanity has sunk its heavy teeth into you and injected its poison and diffused a great stench. It has thrown away some parts, after having mutilated them; other parts it has torn to pieces, again others devoured. And, if it were possible for someone to see vanity and the church in the same arena, the pitiful spectacle might have looked like this—although much more distressing than what happens in the arena—the body thrown away with the beast towering over it and watching over every part of it. The beast drives back anyone who assaults it and does not distance itself or abandon that body. Who then will chase this wild animal away? It is the duty of him who wages this battle to send his angels, invoked by us, and, after they have closed this beast’s daring and impudent mouth as if with braces, they will chase it away. But when he waged the battle it was under the condition that once it was chased away, we would not go after it. And so, after he sends it away, ordering that terrible beast to stay away from us, if we—even after we have been saved from its clutches and it has been chased into its cave—covered with a thousand wounds still go looking for it again and get it roused up and excited again, then he will not have further pity on us, and he will not save us: “Who, in fact, will have pity on a snake charmer bitten by a serpent and on those who get close to the wild beasts?”

Source: ON VAINGLORY AND THE RIGHT WAY FOR PARENTS TO BRING UP THEIR CHILDREN 1