The Countering America Adversaries through Sanctions Act (CAATSA) clearly shows that the United States will counteract Russia and threats stemming therefrom by using sanctions. Among other means, CAATSA provides for secondary sanctions to be imposed on a person who knowingly engages in a significant transaction with a person that is part of, or operates for or on behalf of, the defense or intelligence sectors of the Government of the Russia Federation, irrespective of both where this person is domiciled and conducts its business. The ongoing designation of Russian legal entities and individuals as Special Designated Nationals and Blocked Persons raises before legal science one practical question of the extraterritorial nature of the US legislation and its extension on non-US persons. Russian political leaders, businesses, parastatal entities, and their management long for answers to (i) whether the exterritorial application of sanctions is legal as a matter of US Law; (ii) how American courts apply sanction regulations; and (iii) whether there is any deficiency of law that could be used to evade US sanctions. Based on recent case law of US federal courts, this research deals with the extraterritorial application of US sanctions legislation. The judgment in United States vs Erdal Akova answers the question of why it is difficult for a foreign accused individual to challenge the legitimacy of extraterritoriality in his or her defense. The Judge found that the purpose of the sanctions law is to protect national security – a fact made clear by the name of the basic statute itself: The International Emergency Economic Powers Act can be applied internationally and thus exterritorialy. A conspiracy to violate US sanction that was allegedly formed abroad will lower or even prejudice the chances of success if at least one of the conspirators overtly acted in the US. The subject matter of the second case at issue was a failed attempt of an American partner to evade investment, civil, and contract liability on the basis of extraterritorial violation of US sanctions law committed by his Iranian partner in Iran. The federal judge ruled in favor of the Plaintiff on the payback of investments count, but was reluctant to address the Defendant’s apparent violations of the relevant sanctions regulation and abuse of process. The author criticizes the Judge for a number of flaws and irregularities in law and gives insight on how not to lose one’s investment due to either the formal requirements of the US sanctions regime or an American partner acting in bad faith.