72. 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 ok 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 (CACR) authorize any U.S. person to send $1,000 per quarter to close relatives in Cuba, provided that the recipient is not a prohibited official of the Government of Cuba, as defined in § 515.337 or a prohibited member of the Cuban Communist Party, as defined in § 515.338, or a close relative of such persons, as defined in § 515.339. See 31 CFR § 515.570(a) and (j) for additional applicable conditions. Subject to those conditions, the U.S. remitter can use a third-country provider to send these funds to Cuba. If the person attempts to send more than $1000 per quarter to any one individual, however, he or she may be in violation of U.S. law and subject to penalties. Another example is booking unauthorized travel to Cuba using an internet travel service provider in a third country. Spending money on unauthorized travel-related transactions involving Cuba is prohibited by the CACR, regardless of how the travel is booked or how it is paid for. The fact that the trip was booked through a third-country company, either in person or over the internet, is irrelevant.