ANSWERS: 2
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I believe so, since you are in effect 'importing them'. US customs may or may not confiscate them. . I have heard of people removing the rings and other brand signifiers (the box, if you bought a box) and that stuff to yourself while taking plain cigars through customs. It is unlikely that they're going to do a DNA test after all. . Personally I haven't been that impressed with Cuban cigars versus others from the same general region. I suspect their illegality gives them a mystique but some people swear by them.
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You could get them confiscated by customs at the airport coming back in....
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