Etymology
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Words related to canny

can (v.1)

Old English 1st & 3rd person singular present indicative of cunnan "to know," less commonly as an auxiliary, "to have power to, to be able," (also "to have carnal knowledge"), from Proto-Germanic *kunnjanan "to be mentally able, to have learned" (source also of Old Norse kenna "to become acquainted, try," Old Frisian kanna "to recognize, admit, know," German kennen "to know," Middle Dutch kennen "to know," Gothic kannjan "to make known"), from PIE root *gno- "to know."

It holds now only the third sense of "to know," that of "to know how to do something" (as opposed to "to know as a fact" and "to be acquainted with" something or someone). Also used in the sense of may, denoting mere permission. An Old English preterite-present verb, its original past participle, couth, survived only in negation (see uncouth), but compare could. The present participle has spun off with a deflected sense as cunning.

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-y (2)
adjective suffix, "full of or characterized by," from Old English -ig, from Proto-Germanic *-iga- (source also of Dutch, Danish, German -ig, Gothic -egs), from PIE -(i)ko-, adjectival suffix, cognate with elements in Greek -ikos, Latin -icus (see -ic). Originally added to nouns in Old English; used from 13c. with verbs, and by 15c. even with other adjectives (for example crispy).
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.

uncanny (adj.)

1590s, "mischievous;" 1773 in the sense of "associated with the supernatural," originally Scottish and northern English, apparently from un- (1) "not" + canny (q.v.) in one of its specialized senses in 18c. Scottish English. But canny itself also had a sense of "superstitiously lucky; skilled in magic."

In Wright's "English Dialect Dictionary" (1900) the first sense of uncanny as used in Scotland and the North is "awkward, unskilful; careless; imprudent; inconvenient." The second is "Unearthly, ghostly, dangerous from supernatural causes ; ominous, unlucky ; of a person : possessed of supernatural powers".