US military contingency planning for Cuba has intensified in recent months under the Trump administration, with the Army Reserve assessing logistics, medical, engineering, and military police support units for US Southern Command as early as late 2026, alongside earlier reconnaissance of Cuban waters and examination of air assault options. This occurs amid escalated economic measures including fuel shipment seizures, expanded sanctions on Cuban military-linked and nickel entities, and an ongoing oil embargo that has contributed to severe shortages and blackouts on the island. President Trump has publicly stated that military action is unlikely and that a deal remains possible given Cuba’s economic difficulties, while Cuban officials report maintained communication channels without formal negotiations and have increased defensive preparations. These developments, set against historical US-Cuba tensions and Guantanamo Bay operations, shape trader assessments of whether diplomatic or coercive pathways will lead to military engagement.