early 14c., "learned, skillful," present participle of cunnen "to know" (see can (v.1)). Sense of "skillfully deceitful" is probably late 14c. As a noun from c. 1300. Related: Cunningly.
1580s, "skillful, cunning," from Latin daedalus, from Greek daidalos "skillful, cunningly wrought." Also an anglicized form of the name Daedalus from Greek mythology (1610s).