Originally Posted by
JD3030
Is there any chance I might get tagged at the GE kiosk for my trip to Cuba?
Possible, but quite unlikely. Since Obama took office, OFAC has essentially stopped pursuing penalties for unlicensed travel to Cuba.
See http://www.fas.org/sgp/crs/row/RL31139.pdf (p. 22). It's hard to see why they would go to the effort of tagging unlicensed visitors when they aren't pursuing penalties.
Still, your cigars are contraband. You're rolling the dice with those.