Etymology
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ingenuity (n.)

1590s, "honor, nobility," from French ingénuité "quality of freedom by birth" and directly from Latin ingenuitatem (nominative ingenuitas) "condition of a free-born man," figuratively "frankness, generosity, noble-mindedness," from ingenuus "frank, candid, noble" (see ingenuous).

Etymologically, this word belongs to ingenuous, but in 17c. ingenious "intellectual, talented" and ingenuous so often were confused (even by Shakespeare) that ingenuity in English has come to mean only "capacity for invention or construction." That sense of this word is first attested 1640s; the word for it in Middle English was ingeniosity (the native word is craftiness). French ingénuité, meanwhile, has evolved through "natural and graceful freedom of manners" to "graceful simplicity" (compare ingenue); for the sense "ingeniousness," French uses ingéniosité.

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frank (adj.)

c. 1300, "free, liberal, generous;" 1540s, "outspoken," from Old French franc "free (not servile); without hindrance, exempt from; sincere, genuine, open, gracious, generous; worthy, noble, illustrious" (12c.), from Medieval Latin francus "free, at liberty, exempt from service," as a noun, "a freeman, a Frank" (see Frank).

Frank, literally, free; the freedom may be in regard to one's own opinions, which is the same as openness, or in regard to things belonging to others, where the freedom may go so far as to be unpleasant, or it may disregard conventional ideas as to reticence. Hence, while openness is consistent with timidity, frankness implies some degree of boldness. [Century Dictionary]

A generalization of the tribal name; the connection is that Franks, as the conquering class, alone had the status of freemen in a world that knew only free, captive, or slave. For sense connection of "being one of the nation" and "free," compare Latin liber "free," from the same root as German Leute "nation, people" (see liberal (adj.)) and Slavic "free" words (Old Church Slavonic svobodi, Polish swobodny, Serbo-Croatian slobodan) which are cognates of the first element in English sibling "brother, sister" (in Old English used more generally: "relative, kinsman"). For the later sense development, compare ingenuity.

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outsmart (v.)

"to prove too clever for, get the better of by craft or ingenuity," 1926, from out- + smart (adj.). Related: Outsmarted; outsmarting.

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weaver (n.)
mid-14c. (mid-13c. as a surname), agent noun from weave (v.). The weaver-bird (1826) so called from the ingenuity of its nests.
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capture (v.)

"take or seize by force or stratagem," 1779, from capture (n.); in chess, checkers, etc., "win by ingenuity or skill," 1819. Related: Captured; capturing. Earlier verb in this sense was captive (early 15c.).

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engineer (v.)
1818, "act as an engineer," from engineer (n.). Figurative sense of "arrange, contrive, guide or manage (via ingenuity or tact)" is attested from 1864, originally in a political context. Related: Engineered. Middle English had a verb engine "contrive, construct" (late 14c.), also "seduce, trick, deceive" (c. 1300) and "put to torture."
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outwit (v.)

"to get the better of by superior wits, defeat or frustrate by superior ingenuity," 1650s, from out- + wit (n.). Related: Outwitted; outwitting. Middle English had a noun outwit "external powers of perception, bodily senses; knowledge gained by observation or experience" (late 14c.; compare inwit).

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puzzle (n.)

c. 1600, "state of being puzzled," from puzzle (v.); meaning "perplexing question, difficult problem" is from 1650s; that of "a toy contrived to test one's ingenuity" is from 1814. Puzzle-ring "number of small rings intertwined inseparably with one another that can be arranged as a single ring" is by 1877.

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cunning (adj.)

early 14c., conning, "learned, skillful, possessing knowledge," present participle of connen, cunnen "to know," from Old English cunnan (see can (v.1)), from PIE root *gno- "to know." Also compare cun (v.). Sense of "skillfully deceitful, characterized by crafty ingenuity" is probably by late 14c. Related: Cunningly.

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subtlety (n.)
c. 1300, sotilte, "skill, ingenuity," from Old French sotilte "skillfulness, cunning" (Modern French subtilité), from Latin subtilitatem (nominative subtilitas) "fineness; simplicity, slenderness," noun of quality from subtilis "fine, thin, delicate" (see subtle). From late 14c. as "cleverness, shrewdness; trickery, guile, craftiness," also "thinness, slenderness, smallness; rarity." The -b- begins to appear late 14c. in English, in imitation of Latin.
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