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Can I send money to a sanctioned country using a third-country company's website? Can I buy gifts for someone in a sanctioned country over the internet? The websites tell me that it's o.k. because they themselves are not sanctioned parties.
You cannot do something indirectly that you would not be able to do directly. Therefore, these sites can be used to facilitate authorized transactions, but you cannot use them to perform a transaction which would be in violation of U.S. law. For example, the Cuban Assets Control Regulations authorize any U.S. person to send $300/quarter to any individual in Cuba. The U.S. remitter can use a third-country provider to send these funds to Cuba. If the person attempts to send more than $300/quarter to any one individual, however, he or she is in violation of U.S. law and subject to penalties. Another example is booking tourist travel to Cuba using an internet travel service provider in a third country. Spending money on tourism is prohibited by the CACR, regardless of how the travel is booked or how it is paid for. Ultimately some of these funds will end up in Cuba in violation of U.S. law. The fact that the trip was booked through a third-country company, either in person or over the internet, is irrelevant.
Office of Foreign Assets Control (OFAC), U.S. Treasury Department
http://www.treas.gov/offices/enforcement/ofac/
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