knowing

adjective

1
highly educated; having extensive information or understanding
knowing instructors
a knowledgeable critic
2
evidencing the possession of inside information
3
alert and fully informed
a knowing collector of rare books
surprisingly knowledgeable about what was going on
4
characterized by conscious design or purpose
intentional damage
a knowing attempt to defraud

Also useful for “knowing”:Scrabble— High-value letters — see what it scores