Quote Originally Posted by F.T. Pulver
But, as Tim said, it is illegal for an American to purchase a Cuban cigar under any conditions.
Just to clarify - it is NOT ILLEGAL for an American to purchase a Cuban cigar under any conditions. You just cannot bring it/import it to the US (AOARoss, I don't know if base counts as "US"). Check out the link http://www.cbp.gov/xp/cgov/travel/al...ban_cigars.xml and make your own determination.

So when you're in Thailand or Japan, buy 'em, enjoy 'em, just don't take 'em back to base. And above all, don't advertise what you're doing.