cunning

Etymology 1

From Middle English cunning, kunning, konnyng, alteration of earlier Middle English cunninde, kunnende, cunnand, from Old English cunnende, present participle of cunnan (“to know how to, be able to”), equivalent to con + -ing. Cognate with Scots cunnand (“cunning”), German könnend (“able to do”), Icelandic kunnandi (“cunning”). More at con, can.

adj

1. Sly; crafty; clever in surreptitious behaviour.
2. (obsolete) Skillful, artful.
3. (obsolete) Wrought with, or exhibiting, skill or ingenuity; ingenious.
   cunning work
4. (US, colloquial, dated) Cute, appealing.
   everybody gives something to the cunning little boy; his eyes are large and soft, and he wears a pointed hat, and tight breeches, and jacket 1857, Barbara H. Channing, The Sisters Abroad, Or, an Italian Journey

Etymology 2

From Middle English cunning, kunnyng, partially from Old English *cunning (verbal noun), from Old English cunnan (“to know how to, be able to”); partially from Old English cunnung (“knowledge, trial, probation, experience, contact, carnal knowledge”), from cunnian (“to search into, try, test, seek for, explore, investigate, experience, have experience of, to make trial of, know”), equivalent to con + -ing.

noun

1. Practical knowledge or experience; aptitude in performance; skill, proficiency; dexterity.
   indeed at this very moment he's slipped away with the utmost cunning into a form that's most perplexing to investigate. 2005, Plato, translated by Lesley Brown, Sophist, page 236d
2. Practical skill employed in a secret or crafty manner; craft; artifice; skillful deceit; art or magic.
3. The disposition to employ one's skill in an artful manner; craftiness; guile; artifice; skill of being cunning, sly, conniving, or deceitful.
4. The natural wit or instincts of an animal.
   the cunning of the fox or hare
5. (obsolete) Knowledge; learning; special knowledge (sometimes implying occult or magical knowledge).