US military contingency planning for potential operations against Cuba has advanced through 2026, including Army Reserve assessments for SOUTHCOM support units, reconnaissance near the island, and review of air assault options involving the 101st Airborne Division. These steps coincide with administration accusations that Havana hosts Russian, Chinese, and Iranian capabilities plus transnational groups. Economic pressure has intensified via fuel shipment seizures, sanctions on military-linked entities, and an oil embargo that has deepened Cuba’s energy and infrastructure crises. President Trump has publicly stated that a deal remains likely and military action is unnecessary, while Cuba reports ongoing communication channels without formal negotiations or willingness to alter its political system. Guantánamo Bay has seen expanded autonomous systems deployment. No deployment orders have been issued, and trader focus centers on whether sanctions and diplomacy produce results before any escalation.