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Answer:
HIPTO
Possible Questions:
Aware of
Informed about
Familiar with
Savvy about
In the know about
In on
Not in the dark about
Aware of, slangily
Aware of, to cool cats
Knowing what's what about
In on, slangily
Huey Lewis and the News tune, "___ Be Square"
Digging, in a sense
Aware of, so to speak
Aware of, in '60s slang