Over the last six months, the Trump Administration has demonstrated a renewed focus on efforts to pressure the Cuban government to change its domestic and foreign policies, in particular its support for the Maduro regime in Venezuela. Then-National Security Advisor John Bolton laid out the administration’s approach, including a number of concrete policy changes, in an April 17, 2019 speech to veterans of the Bay of Pigs invasion. These changes will be fully effective by October 9, 2019. Potentially the most significant of these changes is the Trump Administration’s decision to cease issuing waivers under Title III of the Cuban Liberty and Democratic Solidarity (LIBERTAD) Act of 1996 (often referred to as the “Helms-Burton Act”), thereby allowing suits by U.S. nationals against persons who “traffic” in property confiscated by the Cuban government following the 1959 Cuban Revolution to proceed, effective May 2, 2019. In addition, in a series of actions, the U.S. Department of the Treasury’s Office of Foreign Assets Control and the U.S. Department of Commerce’s Bureau of Industry and Security have amended their regulations to re-impose restrictions on certain non-family travel to Cuba, impose new requirements and limitations on remittances to Cuba, and eliminate the authorization for banking institutions subject to U.S. jurisdiction to process certain kinds of financial transactions involving or related to Cuba. Separately, in June, OFAC announced three enforcement actions in one day against travel services providers for violations of its Cuba regulations. In light of the recent regulatory changes and the Administration’s renewed focus on pressuring the Cuban government, both U.S. and non-U.S. firms should consider existing and future business involving or related to Cuba with the understanding that recent changes in U.S. policy likely has increased the sanctions risk associated with such relationships.