Under the second Trump administration, US policy toward Cuba centers on sustained maximum pressure through reinstated state sponsor of terrorism designations, expanded executive orders authorizing secondary sanctions, and targeted measures against military-linked entities like GAESA and the state oil firm CUPET. These steps, including tariffs on third-country oil shipments and restrictions on foreign investment, have intensified the economic embargo and contributed to Cuba’s energy shortages and reform efforts that have yet to produce verifiable progress toward privatization or political concessions. Diplomatic channels remain open but stalled, with Cuban officials reporting no active negotiations or agendas as of early September. Trader consensus on an economic deal reflects these barriers, though scheduled UN General Assembly consideration of the embargo in late October could test diplomatic momentum without altering core US demands for structural changes.