I've probably flown 20+ times (I know, not a lot for some of you) with my Haliburton and my Otterbox loaded with dozens of banded Cuban cigars. They have opened the Haliburton twice, and one time asked (in curiousity, not accusingly) if the Cigars were Cuban. "Yeah, right....I wish" I responded.
I would never put my cigars in a checked bag.
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Thanks Dave, Julian, James, Kelly, Peter, Gerry, Dave, Mo, Frank, Týr and Mr. Mark!