2 Timothy 4:2

Preach the word; be diligent in season, out of season; reprove, rebuke, exhort with all longsuffering and doctrine.
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Ambrose of Milan

AD 397
Accordingly, the apostle says, “What do you wish? Shall I come to you with a rod, or in love and a spirit of meekness?” He mentioned a rod first, striking those who were astray as with an almond rod, that he might afterwards comfort them with the spirit of meekness. So the man whom the rod deprived of the heavenly sacraments was restored by meekness. He gave similar instructions to his disciple also, saying, “Reprove, exhort, rebuke,” two stern words and one gentle, but stern only that he might soften them. To bodies sick with excess of gall, bitter food and drink taste sweet and, on the other hand, sweet dishes taste bitter. Similarly when the mind is wounded, it sickens under the attentions of an unctuous flattery and is again tempered by the bitterness of correction.

Athanasius the Apostolic

AD 373
It is our duty and obligation to remember and heed the special day of Easter Sunday every year. St. Paul taught his disciple Timothy to be aware of dates, saying, “Stand ready in season and out of season.” Paul wrote that, of course, so that Timothy would do things when they were supposed to be done and avoid the blame for doing things at the wrong time.
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Augustine of Hippo

AD 430
I know that it is written, “In the multitude of words you shall not avoid sin.” But would that I were to speak only by preaching your word and by praising you, Lord! Not only would I avoid sin, but I would obtain a good reward, no matter how many words I spoke in this way. For the blessed Paul would not command a sin to his own true son in the faith, to whom he wrote, “Preach the word, be urgent in season, out of season.” For are we to say that a man did not speak many words, who not only in season but also out of season did not keep silent, O Lord, respecting your word? But they were not many, therefore, because they were only what was necessary. .

Benedict of Nursia

AD 547
In his teaching the abbot is ever to observe this rule of the apostle: “Reprove, beseech, correct.” This consists in a judicious timing: to mix gentleness with sternness—at one time to show the severity of a master, at another the tenderness of a father. Use rigor with the irregular and the turbulent, but win to better things the obedient, mild and patient. Rule of St.
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George Leo Haydock

AD 1849
In season, out of season; i.e. whether the hearers are willing to hearken to thee or not. Or, as others understand it, whether it be convenient or inconvenient for thee to signify that the ministers of God must not desist from preaching, whatever troubles they are under. (Witham)
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Gregory The Dialogist

AD 604
Pastoral guides must also see to it with careful concern that not only should nothing evil proceed from their lips but that not even what is proper be said in excess or in a slovenly manner. Often the force of what is said is wasted when it is enfeebled in the hearts of the hearers by a careless and offensive torrent of words. Indeed, this sort of loquacity defiles the speaker himself, inasmuch as it takes no notice of the practical needs of the hearer…. Thus Paul also, admonishing his disciple to be constant in preaching, said: I charge you before God and Jesus Christ, who shall judge the living and the dead, by his coming and his kingdom: preach the word, be instant in season, out of season. When he was about to say “out of season,” he premised it with “in season,” for if being in season is not combined with being out of season, the preaching destroys itself in the mind of the hearer by its worthlessness.

John Chrysostom

AD 407
Therefore, let food, and bathing, and banqueting, and the other necessities of life have a definite time. But let instruction about the love of truth from above have no set hour—let all the time belong to it. “In season, out of season, reprove, entreat, rebuke,” Scripture says. And the prophet, “On his law he will meditate day and night.” And Moses too asked the Jews to do this continually.
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John Chrysostom

AD 407
Let it always be your season, not merely in peace and security and when sitting in the church.
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John Chrysostom

AD 407
Whether you are in danger, in prison, in chains or going to your death, at that very time do not hesitate to admonish. Do not withhold your admonition. For it is then most seasonable, when your rebuke will be most successful, when the circumstance is at hand. “Exhort,” he says. After the manner of physicians, having shown the wound, he makes the incision, he applies the remedy. If you omit either of these, the other becomes useless. If you rebuke without convicting, you will seem to be rash, and no one will tolerate it. After the matter is proved, one will submit to rebuke. But before this, he will be headstrong. If you convict and rebuke, but vehemently, but do not apply exhortation, all your labor will be lost. For conviction is intolerable in itself if consolation is not mingled with it.

John Chrysostom

AD 407
What means in season, out of season? That is, have not any limited season: let it always be your season, not only in peace and security, and when sitting in the Church. Whether thou be in danger, in prison, in chains, or going to your death, at that very time reprove. Withhold not rebuke, for reproof is then most seasonable, when your rebuke will be most successful, when the reality is proved. Exhort, he says. After the manner of physicians, having shown the wound, he gives the incision, he applies the plaster. For if you omit either of these, the other becomes useless. If you rebuke without convicting, you will seem to be rash, and no one will tolerate it, but after the matter is proved, he will submit to rebuke: before, he will be headstrong. And if you convict and rebuke, but vehemently, and do not apply exhortation, all your labor will be lost. For conviction is intolerable in itself if consolation be not mingled with it. As if incision, though salutary in itself, have not plenty o...

John of Damascus

AD 749
That is to say, do not think its not time to preach, always let it be that time for you, not just in peace or in gladness, nor should you teach only in Church while you are being censored, but even if you are in prison laying in chains, do not cease preaching.
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Severian of Gabala

AD 425
The opportune time for preaching and teaching is when the sinner needs the prophylaxis that will lead him to repentance. The sinner will be helped at exactly the right moment between the intention to sin and the commission of sin and will turn to penitence instead. .
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Knowing this first, that no prophecy of the scripture is of any private interpretation - 2 Peter 1:20

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