Proverbs 26:5

“Answer a fool according to his folly, etc.] The Targum is, “but speak with a fool in thy wisdom;” and the Syriac version, “yea, speak with a fool according to thy wisdom;” which would at once remove the seeming contradiction in these words to the former, but then they are not a true version; indeed it is right, and must be the sense, that when a fool is answered, as it is sometimes necessary he should, that it be done in wisdom, and so as to expose his folly; he is to be answered and not answered according to different times, places, and circumstances, and manner of answering; he is to be answered when there is any hope of doing him good, or of doing good to others; or of preventing ill…”

“Answer--by reproof.”

“Two sides of a truth. To “answer a fool according to his folly” is in Proverbs 26:4 to bandy words with him, to descend to his level of coarse anger and vile abuse; in Proverbs 26:5 it is to say the right word at the right time, to expose his unwisdom and untruth to others and to himself, not by a teaching beyond his reach, but by words that he is just able to apprehend. The apparent contradiction between the two verses led some of the rabbis to question the canonical authority of this book. The Pythagoreans had maxims expressing a truth in precepts seemingly contradictory. return to 'Top of Page'”

“According - So as his folly needs and requires, convincing him strongly, reproving him sharply, and exposing him to just shame. Proverbs 26:6”

“a fool: Kg1 22:24-28; Jer 36:17, Jer 36:18; Mat 15:1-3, Mat 16:1-4, Mat 21:23-27, 22:15-32; Luk 12:13-21, Luk 13:23-30; Joh 8:7, Joh 9:26-33; Tit 1:13 lest: Pro 26:12, Pro 28:11; Rom 11:25 conceit: Heb. eyes, Isa 5:21; Rom 12:16 Proverbs 26:6”

“5 Answer the fool according to his folly, Lest he regard himself as wise. ענה־כסיל (with Makkeph, and Gaja, and Chatef) (Note: Thus after Ben Asher; while, on the contrary, Ben Naphtali writes ענה כסיל with Munach, vid., Thorath Emeth, p. 41.) here stands opposed to אל־תען כסיל. The Gospel of John, e.g., Joh 5:31, cf. Pro 8:31, (Note: Vid., my dissertation on three little-observed passages in the Gospel of John, and their practical lessons, in the Evang. luth. Kirchenzeitung, 1869, Nos. 37, 38.) is rich in such apparently contradictory sayings. The sic et non here lying before us is easily explained; after, or according to his folly, is this second time equivalent to, as is due to his folly:…”