The Trump administration has maintained and expanded a maximum-pressure sanctions regime against Cuba since January 2026, including executive orders that authorize tariffs on third countries supplying oil and designate Cuba’s state-owned oil company CUPET for blocking sanctions. These steps followed the cutoff of Venezuelan crude after Maduro’s capture and have contributed to severe fuel shortages, repeated nationwide blackouts, and an acute energy crisis on the island. Limited humanitarian carve-outs, such as licenses for private-sector resale of Venezuelan oil, have not altered the broader blockade posture. No official announcements or diplomatic signals of broad oil-sanction relief have emerged through mid-August 2026. Market resolution hinges on whether the administration issues a public statement or formal action easing restrictions before the contract deadline, an outcome tied to ongoing bilateral dynamics, Cuban policy responses, or shifts in U.S. enforcement priorities.