US military contingency planning for Cuba has intensified amid ongoing economic sanctions and an oil blockade, with September 2026 reports detailing Army Reserve assessments for logistics, engineering, medical, and military police units potentially available to Southern Command within 90-120 days. Earlier 2026 activities included maritime reconnaissance and airpower readiness reviews, though no deployment orders have been issued. President Trump has repeatedly stated that military action is unlikely, emphasizing expectations of a bilateral deal, Cuba’s economic difficulties, and a preference for opening the island to US influence. Cuban officials have rejected formal negotiations while maintaining communication channels and bolstering defensive preparations against possible aggression. These developments, alongside Guantanamo Bay infrastructure updates, shape trader assessments of near-term escalation risks.