But in a 2002 letter, OFAC's director at the time, Richard Newcomb, said the Internet had transformed those booking systems into commercial ventures where financial transactions take place. As a result, the subsidiary was banned from selling Cuba trips. Clif Burns, an export lawyer specializing in Cuba, said the matter seemed settled with the letter. An OFAC official who did not want to be identified said Travelocity was the first large online travel provider to face an OFAC fine.

Still, the issue has gotten complicated amid the globalization trend.

Burns said European Union regulations bar companies operating in member countries from denying commerce to Cuba — a rule that would apply to U.S. subsidiaries. He said EU regulators have not enforced the 1996 rule, so most U.S. companies adhere to Washington's protocol toward Havana.

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