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Psalms 142:1 (Maschil of David; A Prayer when he was in the cave.) I cried unto the LORD with my voice; with my voice unto the LORD did I make my supplication.
Psalms 142:1 Word Study on “Maschil” Gesenius says the Hebrew word “Maschil” ( מַשְׂכִּיל ) (H4905) is a participle meaning, “a didactic poem.” Strong it means, “instructive,” thus “a didactic poem,” being derived from ( שָׂכַל ) (H7919), which literally means, “to be circumspect, and hence intelligent.” The Enhanced Strong says it is found 13 times in the Old Testament being translated in the KJV all 13 times as “Maschil.” It is used as a title for thirteen of the 150 psalms (Psalms 32:0; Psalms 42, 44, 45, 52 through 55; 74; 78; 88; 89; 142).
Most modern translations do as the KJV and transliterate this Hebrew word as “maschil,” thus avoiding the possibility of a mistranslation. The LXX reads “for instruction.” YLT reads “An Instruction.” Although some of these psalms are didactic in nature, scholars do not feel that all fit this category. The ISBE says, “Briggs suggests ‘a meditation,’ Thirtle and others ‘a psalm of instruction,’ Kirkpatrick ‘a cunning psalm.’” 
 John Richard Sampey, “Psalms,” in International Standard Bible Encyclopedia, ed. James Orr (Grand Rapids, Michigan: Wm. B. Eerdmans Publishing Co., c1915, 1939), in The Sword Project, v. 1.5.11 [CD-ROM] (Temple, AZ: CrossWire Bible Society, 1990-2008).
Psalms 142:1 “A Prayer when he was in the cave” - Comments - This is probably a reference to the cave Adullam or the cave in the wilderness of Engedi (1 Samuel 22:1; 1 Samuel 24:1-9.24.3).
1 Samuel 22:1, “David therefore departed thence, and escaped to the cave Adullam : and when his brethren and all his father's house heard it, they went down thither to him.”
1 Samuel 24:1-9.24.3, “And it came to pass, when Saul was returned from following the Philistines, that it was told him, saying, Behold, David is in the wilderness of Engedi . Then Saul took three thousand chosen men out of all Israel, and went to seek David and his men upon the rocks of the wild goats. And he came to the sheepcotes by the way, where was a cave; and Saul went in to cover his feet: and David and his men remained in the sides of the cave.”
Psalms 142:2 I poured out my complaint before him; I shewed before him my trouble.
Psalms 142:1-19.142.2 Comments - Psalms 142:1-19.142.2 is Hebrew parallel poetry in which each verse states parallel thoughts.
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Everett, Gary H. "Commentary on Psalms 142". Everett's Study Notes on the Holy Scriptures. https://www.studylight.org/
the Second Week of Advent