Two Separate Cuba Sanctions Laws Create Legal Exposure on Both Sides of Same Transaction

U.S. Cuba sanctions operate on dual, non-overlapping legal tracks. OFAC licenses authorize Americans to pay for certain transactions—including hotel stays—while Helms-Burton Title III (activated in 2019 after decades of presidential waivers) allows U.S. nationals to sue foreign companies profiting from property seized by Cuba after 1959. A licensed American tourist's payment may be legal; the foreign hotel operator faces potential U.S. court liability. Compliance requires separate analysis of each framework.